faulty communication: the bottom line · 2018-02-27 · robyn taylor ph/fax (03) 9328 2033/2670...

ALSO IN THIS ISSUE: At work with heavy hydrogen • Chemical reactions make cohesive concrete • Behind the scenes at Agilent

in AustraliachemistryMay 2015

chemistryFaulty communication: the bottom line

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news & research5 On the market8 News12 Research42 Events42 Cryptic chemistry

members4 From the President30 RACI news31 Obituary

views & reviews6 Your say32 Books35 Instrumentation36 Economics38 Education39 Grapevine40 Plants & soils41 Letter from Melbourne

22 Heavy hydrogen: making the most of conductive moleculesMolecular deuteration is making its mark in the expanding field ofoptoelectronics.

26 Bomb-proofing buildingsA new form of reinforced concrete that can absorb the blast of an explosion isbeing developed for use in buildings that can withstand terrorist attacks.

War of wordsThe L’Aquila earthquake convictions are a reminder that communicating riskis a risk in itself.

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People join RACI for a variety of reasons. I joined in the last millennium (1986) during the Honours

year of my degree at the University of Newcastle. The drivingforce was unusual, but not unique, because all of my fellowHonours students that year did the same. We all had, as agroup, spent a lot of time solving the (then) annual RACICryptic Chemistry Crossword created by Dr Malcolm McCamishfrom the University of Queensland. We feared that our entrywould be invalid unless we were RACI members so we all dulyjoined. Our entry was correct and we received an attractivecertificate in the post, but not the famed ‘handsome trophy’ forthe ultimate winner.

I never knew whether RACI membership was a requirement toenter this competition. Ironically, when I joined the ChemistryDepartment at the University of Queensland in 1994, I finallymet Malcolm face to face and I told him my story. Malcolmadmitted sheepishly his membership had lapsed years ago buthe was still compiling cryptic crosswords for Chemistry inAustralia. Now a cryptic chemistry crossword appears in everyissue of Chemistry in Australia (thanks to the sustained effortsof Graham Mulroney), but almost 30 years on and without all ofmy colleagues to help I am hopelessly out of my depth!

So, apart from chemistry cryptic crosswords, why have Iremained an RACI member all this time? There are significanteconomic benefits of membership. The many conferences andsymposia that RACI runs offer members significantly discountedregistration fees, often in excess of annual membership.Chemistry in Australia (including its crossword) is anotherbenefit and its engaging content and presentation (hard copyor online) is something I look forward to every month. Theseare benefits that all RACI members enjoy passively.

However, the greatest benefit that I have derived from RACImembership is when I have been actively involved. I joined theQueensland Branch Committee in 1995 and for the first time Ibegan to see the breadth and diversity of RACI events(conferences, symposia, career development etc.) outside my

own interests and meet chemists from different sectors (otheruniversities, industry, teachers and government organisations).

An overseas sabbatical in 2000 meant that I stepped downfrom the Committee and I fell back into passive membership. In2007, I became Chair of the RACI Inorganic Chemistry Division(2007–10) and joined the RACI Assembly – the elected 14Divisional Chairs and eight Branch Presidents and the principaladvisory group to the RACI Board. Here I saw how the RACIreally functioned on so many levels and its role as a nationalnetwork of professional chemists.

When the opportunity arose to be nominated for theposition of RACI President Elect in 2012, I didn’t hesitate.Joining (and now chairing) the RACI Board, the group thatcollectively makes the decisions that shape the Institute, hasbeen, and continues to be, one of the most rewardingexperiences of my professional life.

Not everyone wants to be RACI President (it’s a lot of work!);involvement in the RACI can be at many of the abovementionedlevels. What we need is your input, ideas and initiatives. Isthere is an area of chemistry (research, education, industry,government etc.) that would benefit from the establishment ofa new group (local or national) or even running events thatwould be of interest to RACI members? RACI will provide theresources and infrastructure to help you get started and gathermomentum. That’s really what RACI is – a network (or family) ofchemists who share a professional interest in chemistry.

If you want to become involved, your first point of contactcan be me or perhaps your Branch President. To paraphrase anoften quoted speech, ask not what your Institute can do for youbut …

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Chemistry in Australia4 | May 2015

from the raci

From the President

Paul Bernhardt FRACI CChem ([email protected]) is RACI President.

on the market

Chemistry in Australia 5|May 2015

Mira M – handheld Ramanspectrometers with ORStechnologyMetrohm is pleased to introduce theMetrohm Instant Raman Analysers(Mira). The Mira spectrometers arethe only handheld Raman analysersavailable with Orbital-Raster-Scan(ORS) technology. This highlyreproducible averaging techniqueextends the scope of possiblesamples to any kind ofheterogeneous and sensitivematerials.

The Mira analysers arehandheld, high-performancespectrometers for rapid, non-destructive analysis of chemical andpharmaceutical samples, be they liquid or solid. Barelylarger than a smartphone, the Mira analysers may be usedanywhere: in the warehouse, in the process, in the field,and – of course – in the laboratory. The user benefits ofMira in a nut-shell:• Light, compact and handy – single-handed operation • Instantly ready to use in any place• Fast and reliable real-time results – no sample

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MicroCal PEAQ-ITC – advancedand easy to useIsothermal titration calorimetry (ITC) is a technique usedto measure and characterise biomolecular bindinginteractions. ITC works by directly measuring the heat thatis either released or absorbed during a biomolecularbinding event. ITC is the only technique that cansimultaneously determine binding parameters such asbinding affinity (Kd), stoichiometry (n), enthalpy (DH) andentropy (DS) in a single experiment. Requiring nomodification, either with fluorescent tags or throughimmobilisation, ITC measures the affinity of bindingpartners in their native states. Applications range fromdrug discovery and design, for characterising biomolecularinteractions to fundamental research such as theunderstanding and regulation of signal transductionpathways.

One of the challenges associated with the measurementand characterisation of binding interactions is the broadaffinity range that needs to be addressed, which typicallyspan from low millimolar to subnanomolar range.

The new MicroCalPEAQ-ITC isdesigned for ease ofuse and exceptionalsensitivity. The wideaffinity rangeenables analysis ofweak to highaffinity binders withexcellentreproducibility. Thenon-reactive

Hastelloy cell ensures chemical resistance and compatibilitywith biological samples while the high-precision pipetteenables smaller injection volumes. The high signal to noise,fully automated options for unattended operation and auser-friendly guided workflow ensure data analysisconsistence for confident decision-making.

For over 25 years ATA Scientific have supplied andsupported their customers with innovative scientificinstruments. We are now the new local distributor forMicroCal ITC/DSC products. These systems are in use in over1000 labs worldwide, both for R&D and commercialapplications and have over 10000 citations in referencedatabases.

For further details, contact ATA Scientific Pty Ltd, ph. (02) 9541 3500, email [email protected] visit www.atascientific.com.au.

your say

6 | May 2015Chemistry in Australia

Hy-Cycle commercialisationI enjoyed Professor Aguey-Zinsou’s article on a hydrogen fuelcell bicycle, and learned a lot about the storage of hydrogenusing borohydrides (March issue, p. 16). However, I have somedoubts about the commercial viability of such a product. Notethat I am not questioning the technical aspects at all, nor am Iquestioning the project as a valuable learning exercise forstudents. I guess if someone were to come to me and ask me tofund a commercial venture to manufacture these vehicles, Iwould want to ask at least three questions up front.1 Who do you see as the market?2 What is the competition?3 How much is it going to cost?

In terms of question 1, I would be asking such things as:who is the likely purchaser, what is an estimate of the likelycommute distance, where and when is it likely to be used?

Concerning competition, this is a product that clearlyalready has competitors in the marketplace. Looking at justbicycles (and not other vehicles on the road), I would nominatethe common push bike, and bicycles fitted with battery-poweredelectric motors or small petrol motors. The fuel cell electric bikeis clearly most similar to the battery-powered bike, and shouldbe compared to that product first up. How many battery-powered bikes are sold per year? What percentage of thismarket would a fuel-cell bike be expected to capture?Alternatively, would a fuel-cell bike be expected to grow theauxiliary motor bicycle market, and if so, by how much? I wouldnote that the battery-powered bike has the advantage of anestablished infrastructure in the form of mains power to charge

the battery, although in Australia both types rely on mainlycoal-fired power stations as the ultimate source of their energy.

The cost of the product is another factor. Here, the fuel-cellbike runs up against the not-so-humble push bike as acompetitor, especially as this vehicle requires no power supplyinfrastructure. Bear in mind that Aldi sells bikes with 21 gearsfor around $125, and you start to get an idea of thecompetition. For well under $1000 you can get acomprehensively featured commuter bike that will, with amodicum of care, last for many years. With 30 gears andweighing about 11 kilograms, a cyclist with a reasonable levelof fitness can tackle virtually any hill and ride for longdistances. Compare this to the Hy-Cycle. It’s a heavy-lookingclunker, without even considering the 2.5-kilogram hydrogenpack. From what I can see, you’d spend little time pedalling,and most of the time letting the electric motor tow you around.From the few battery-powered bikes I’ve see around, most seemto be used on battery power only (and mostly on thefootpaths!)

I must declare a prejudice against motorised bicycles. I simply can’t see the need. At 73, I have been riding a bike for exercise (an hour a day) for the past 35 years or so. My oldCannondale Headshok mountain bike weighs 12 kilograms, andwith 27 gears, I can climb virtually any hill, although a littlemore slowly these days.

Tom Smith FRACI CChem

I also enjoy riding my bike to go to work. It is a hybrid bikewith an aluminium frame and thus very light. However, when Ihave important meetings I prefer to use my hydrogen bikebecause I can still easily go through Sydney’s traffic and arrivefresh at my meetings. Some of my colleagues also enjoy theflexibility of bicycles and take their kids to school in a biketrailer on their way to work. Once again, electrical assistancetransforms the experience.

Bicycles have become more than a means to exercise. In busycities, they are now a very effective way to commute. The electricbike market is a multibillion dollar industry. China for obviousreasons is one of the biggest markets for electric bikes (about200 million in 2014) – and India is projected to be a biggermarket. In developing countries, electric bikes provide power tomove goods around. But the number of electric bike users is alsorapidly increasing in other parts of the world. Electric bikes arenow 45% of the sales in Germany, 21% in the Netherlands, and5% in France (www.insg.org/%5Cdocs%5CINSG_Insight_23_Global_Ebike_Market.pdf).

Our main reason for building the Hy-Cycle is to demonstratehow simple the technology is. Obviously it can be adapted torun anything that requires power, including a house. Previousdemonstrations of hydrogen use for transport have been doneon buses because of the space needed to host the pressurisedhydrogen tanks (up to 700 bar) and this poses obvious safetyconcerns in case of failure and hydrogen escape. With thetechnology (metal hydrides) that we have implemented on the

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Send your contributions(approx. 400 words) to theEditor at [email protected].

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Hy-Cycle, the use of hydrogen becomes safe because only asmall amount of hydrogen will be released upon rupture of thecanister (way below the flammability limit of hydrogen).

Often, when thinking of implementing new technologies,one adopts current centralised models, and thus in the contextof energy, major investments will be required to build largecentral infrastructures and distribution networks to deliver thehydrogen. In fact, such an approach is not necessary becausehydrogen can be produced from locally available resources, i.e.solar, wind, waves or even organic wastes in the near future.Many Australians are now equipped with solar panels, and witha combined electrolyser/hydrogen storage unit it is very easy toproduce and store some hydrogen for a Hy-Cycle or a hydrogencar – and thus provide people with the ability to produce theirown clean energy. Considering the alternative of electricvehicles, current infrastructures in Australia and in particularthe electrical grid are not capable of taking the extra load andthis will require major investments in addition to thedevelopment of relatively complex ‘intelligent grid concepts’.

In the commercialisation phase, the Hy-Cycle will come withits own hydrogen generator to refill the canisters from tap waterand electricity in 30 minutes. The estimated retail price is$5000 for a range of 125 kilometres and unlike a battery thehydrogen canister will still safely store hydrogen after 25–30 years. Cheaper bicycles can always be produced. However, ina world where the availability of resources is going to be amajor issue, it is time that we shift our society towards moresustainable models where resources are used wisely, productsbecome better designed so they can be repaired and recycled,and people are treated fairly for the work they produce.

Kondo-Francois Aguey-Zinsou

Climate change and thermodynamicsA recent letter to Your Say (March 2015) by B.F. Gray containsseveral misleading criticisms of my response to the letter ofRichard Corbett (Dec 2014/Jan 2015), which I feel I cannotleave without reply. First of all, B.F. Gray objects to theapplication of the laws of thermodynamics to an animalorganism on the basis that animals are open systems. Of courseevery living organism is an open system, as is the Earth as awhole. This doesn’t mean thermodynamics doesn’t apply. Forexample, as we get older it becomes increasingly clear to all ofus that we can’t escape the second law of thermodynamics.Entropy always wins in the end.

Thermodynamics applies universally to all systems, open orclosed. For open systems, if one wishes to calculate theirtemperature, it is necessary to consider the rates of heat flow inand out. For an animal, this means the rate of heat dissipationto the environment and the rate of heat generation viametabolism. This was already explained in my original article‘When the going gets hot’ (June 2013 issue, p. 20), which,based on the contents of his letter, B.F. Gray obviously didn’t

read. Further evidence of this can be found in his latercomments concerning mechanisms of body cooling (sweatingand panting, for example), which although correct, were alsoalready described in my original article. These thermoregulatorymechanisms allow animals to survive at ambient temperaturesabove their body temperature for a period of time and delay theonset of heat-stress. However, there is no denying thatprolonged exposure to high temperatures inevitably leads todeath, an important reason for taking global warming seriously.

Naturally I apologise profusely to B.F. Gray for not citing his1972 article published in Combustion and Flame. However,before writing another letter to the editor, B.F. Gray might alsolike to consider reading the original article on which the lettershe criticises were based.

Ronald J. Clarke

Climate change and professional dutyJim Bonham’s concise, lucid and logical letter (March issue, p. 5) makes me proud to be a chemist. One can only wish thatthe thinking was as clear at our upper levels of government. A question not often discussed is why the populace is notmarching on Canberra. I have distilled the following aboutpublic opinion from my reading, which includes several booksand many of the official reports.• It’s hard to accept that just 1°C can be causing so much

bother.• The whole climate thing is very complex and too darned hard

to understand (this is fanned by lobbying and a hugedisinformation campaign and a media that gives too muchspace and time to ratbags) – but for a quick summary seealso ‘The science of climate change’ from the AustralianAcademy of Science (2010 and 2015 update).

• Science generally has been downgraded, so some arereluctant to accept scientists’ advice.

• The present population is not trained to think in really bigterms such as the cosmos, or in geological time periods orabout whole ecosystems.

• Australia is too small to make any difference (but not toosmall to host the G20 or chair UN committees).

• The idea of any international agreement to take drasticaction seems cloud nine (though agreements have beensigned between various groups of countries and themovement is building).

• And, even for those who begin to understand, climatechange is just too threatening to face up to.I believe that we professionals have a duty to make the real

situation known whenever we can and even to seek outaudiences that we can reach.

Bruce Graham FRACI CChem

news


The Australian Government will recognisethe practical and commercial successes ofAustralian scientists with a new award tobe added to the 2015 Prime Minister’sPrizes for Science.

Minister for Industry and Science IanMacfarlane said that Australians make asignificant investment in science throughan annual government budget of$9.2 billion.

‘The new prize, the Prime Minister’sPrize for the Commercial Application ofScience, will promote building betterlinks between researchers and industryand encourage entrepreneurship in ourbusiness and research communities.

‘Developments in Australian sciencehave the potential to drive theinnovations that create jobs and improveour quality of life.’

In their 15th year, the PrimeMinister’s Prizes for Science recogniseoutstanding achievements in science

research and excellence in scienceteaching, and are Australia’s pre-eminentannual science awards.

The new prize for commercialisation ofscience complements the other prizeswhich have recognised discoveries suchas the cervical cancer vaccine;technology that made wireless computingfast and reliable; evidence of dark matterand dark energy in the universe; andtechnologies that help to make the oiland gas industry safer and more efficient.

Last year’s recipients of the PrimeMinister’s Prize for Science were LaureateProfessor Sam Berkovic and ProfessorIngrid Scheffer of the University ofMelbourne, who led the way in findingthe genetic basis for many types ofepilepsy.

The introduction of the new prizemeans the Government has increased thetotal prize money to $700 000 across thesix prizes to be awarded in 2015.

The Prime Minister’s Prize for Sciencerecognises a significant advancement ofknowledge through science.

The Prime Minister’s Prize for theCommercial Application of Science isawarded for the translation of scienceknowledge into a substantial commercialimpact.

The Frank Fenner Prize for LifeScientist of the Year and the MalcolmMcIntosh Prize for Physical Scientist ofthe Year acknowledge the work of ourbest early to mid-career scientists.

The Prime Minister’s Prize forExcellence in Science Teaching in PrimarySchools and the Prime Minister’s Prize forExcellence in Science Teaching inSecondary Schools recognise excellencein science teaching with prize moneyshared equally between the recipientteacher and their school.MINISTER FOR INDUSTRY AND SCIENCE

New Prime Minister’s Prize for Science

With one in six Australians recordingsome form of auditory loss, a new studyby the University of Queensland isexamining how exposure to chemicals inthe workplace can affect employeehearing.

Led by Dr Adrian Fuente of the Schoolof Health and Rehabilitation Sciences,the study aims to identify the mosteffective hearing tests to detectproblems caused by chemical exposure,and the safe levels of exposure tomaintain healthy hearing at work.

Fuente said certain occupations weremore at risk than others, includingpainters, spray-painters, those working intextile, clothing and footwear factories,and aviation and lab workers.

‘While much is known about thedangers of noise exposure in theworkplace, the public is often unaware ofthe role that certain chemicals can playin causing early hearing loss,’ Fuentesaid.

The study is currently seekingemployees working in the painting,spray-painting, textiles, clothing,aviation and jet fuel, footwear andhistology lab industries to participate inthe research.

As part of the study, participants willhave their hearing tested via non-invasive procedures.

‘There is still not enoughunderstanding of which levels ofchemical exposure are safe for our ears,’Dr Fuente said.

‘I encourage people working in theseindustries to participate in this vitalresearch, the outcomes of which couldhave a definitive impact on theAustralian workplace in the pursuit ofhealthy hearing for all.’

Those interested in participating inthe study should contact Laura Sheridanon [email protected] or phone(07) 3346 7489.UNIVERSITY OF QUEENSLAND

Does chemical exposure in the workplace affect hearing?

iStockphoto/abbejon

Scientists from the Australian National University (ANU) andUniversity of Bristol have discovered how copper ore formsaround volcanoes.

The findings contradict previous theories of how copperforms, and could lead to changes in exploration for copper,which has limited reserves but is crucial for electricitytransmission.

Lead researcher Dr John Mavrogenes, from the ANU ResearchSchool of Earth Sciences, said the research examined whatcauses the large copper deposits, known as porphyries that formaround volcanoes.

‘We found that these copper deposits need rocks containingboth copper and sulfur,’ he said.

‘If you look at the volcanic rocks that typically surroundthese deposits, they are quite rich in copper but very low insulfur.

‘But the much hotter rocks below them have a lot of sulfur.That sulfur is percolating up and kneading these rocks andcausing the porphyries to form.’

Mavrogenes said that this discovery contradicts the existingtheory that the copper deposits were caused by water thatcomes from magma.

The research involved a laboratory simulation of the copperporphyries formation that was able to replicate the naturalprocess.

‘We found that it’s very likely that this process is crucial toporphyry copper formation,’ he said.

Mavrogenes said the research could lead to improvements inthe way mining companies search for copper porphyries.

‘These porphyries are economically huge deposits. There’s acouple of them in Australia from when we had an ancientvolcanic arc here around 400 million years ago,’ he said.

‘What we would suggest that these companies do is to lookmore at the rock and see if it has the kind of composition we’veidentified.’

The research may also be used to develop a betterunderstanding of when volcanos might erupt.

The research was published in Nature Geoscience (doi:10.1038/ngeo2351).AUSTRALIAN NATIONAL UNIVERSITY

9|May 2015 Chemistry in Australia

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How copperforms aroundvolcanoes Dormant volcanoes, such as this one in a Bolivian desert, may

be a future target of copper exploration.

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news

Scientists at Trinity College Dublin haveuncovered a molecule that blocks a keydriver of inflammatory diseases. Thefinding could meet a major unmetclinical need by inspiring new non-invasive treatments for arthritis,multiple sclerosis and Muckle-Wellssyndrome, among a myriad of otherinflammatory diseases.

In a study published in NatureMedicine, the international researchteam led by Trinity and the University ofQueensland showed how the moleculeMCC950 can suppress the ‘NLRP3inflammasome’, which is an activator ofthe key process in inflammatorydiseases.

Inflammasomes have been identifiedas promising therapeutic targets byresearchers over the last decade. Andnow the discovery of MCC950’s abilitiesrepresents a hugely significantdevelopment in the effort to findtreatments for inflammatory diseases, forwhich current therapies are either highlyineffective or have major limitations.

Crucially, the finding also confirmsthat inflammatory diseases all have acommon process, even though the partof the body becoming inflamed mightdiffer.

Professor of Biochemistry at Trinity,Luke O’Neill, is the joint senior scientistbehind the discovery. He said: ‘Drugs likeaspirin or steroids can work in severaldiseases, but can have side effects or beineffective. What we have found is apotentially transformative medicine,which targets what appears to be thecommon disease-causing process in amyriad of inflammatory diseases.’

Lead author Dr Rebecca Coll said:‘MCC950 is blocking what was suspectedto be a key process in inflammation.There is huge interest in NLRP3 bothamong medical researchers andpharmaceutical companies and we feelour work makes a significantcontribution to the efforts to find newmedicines to limit it.’

Professor Matt Cooper, chemist andco-senior author from the University ofQueensland’s Institute for MolecularBioscience, added: ‘MCC950 is able tobe given orally and will be cheaper toproduce than current protein-basedtreatments, which are given daily,weekly, or monthly by injection.Importantly, it will also have a shorterduration in the body, allowingclinicians to stop the anti-inflammatoryaction of the drug if the patient everneeded to switch their immuneresponse back to 100% in order toclear an infection.’

So far, the results have shown greatpromise for blocking multiple sclerosisin a model of that disease, as well asin sepsis, where potentially fatal bloodpoisoning occurs in response tobacteria. However, the target forMCC950 is strongly implicated indiseases such as Alzheimer’s disease,atherosclerosis, gout, Parkinson’sdisease and rheumatoid arthritis, whichmeans it has the potential to treat allof these conditions.

Another disease where the new drugmight have significant benefits isMuckle-Wells syndrome, which is a rareand severe auto-inflammatory disorder.Using blood samples from patients, theauthors showed that MCC950 can blockthe rogue gene responsible for repeatedinflammatory activation in sufferers.

Dr Dan Kastner of the NationalInstitutes of Health USA, said: ‘MCC950might well be a key addition to theoptions for treating Muckle-Wellssyndrome and similar diseases.’

O’Neill added: ‘We are really excitedabout MCC950. We believe this has realpotential to benefit patients sufferingfrom several highly debilitatingdiseases, where there is currently a direneed for new medicines.’

The above story is based onmaterials provided by Trinity CollegeDublin. LABROOTS

Molecular blocker could lead totreatments for inflammatory diseases

Deakin’s Carbon Nexus topartner with DowAksaAustralia’s carbon fibre industry growthstrategy has been given a boost with a newpartnership between Deakin University andDowAksa – a joint venture between providerof acrylic fibre Aksa and The Dow ChemicalCompany.

DowAksa will work with Deakin’s carbonfibre research centre, Carbon Nexus toadvance worldwide market adoption of carbonfibre composites and promote Australianexpertise in materials and manufacturingtechnologies to industrial composite partsmakers and end users such as automotivemanufacturers in North America and Europe.

Carbon Nexus Director Derek Buckmastersaid the DowAksa partnership was a key partof the growth plan for the research facility.

‘We are already working in partnershipwith the world’s first commercial maker ofsingle-piece carbon fibre auto wheels, CarbonRevolution, which is based at our WaurnPonds campus alongside Carbon Nexus, andrecently expanded its operations,’ Buckmastersaid.

‘Australian carbon fibre parts manufacturerQuickstep is also setting up a dedicatedautomotive division at our Waurn Pondscampus to design and develop automotivemanufacturing cells and enable theproduction of customer prototypes and initialproduction quantities.’

DowAksa is a charter member of USadvanced composites consortium awardannounced last month by President BarackObama to establish a national advancedcomposites manufacturing institute.

Subject to final negotiations between thisconsortium and the US Department of Energy,the new institute being formed, called theInstitute for Advanced Composites MaterialsInnovation, will bring more thanUS$250 million in combined federal, state,corporate and academic support to acceleratethe development of an advanced compositesindustry in the US.

Once the new Institute begins operations,the University hopes it will provide anextended platform for collaborativeengagement and networking with businessand academic leaders in the American market.DEAKIN UNIVERSITY


Researchers have long sought an efficientway to untangle DNA in order to study itsstructure – neatly unravelled andstraightened out – under a microscope.Now, chemists and engineers at KULeuven, in Belgium, have devised astrikingly simple and effective solution:they inject genetic material into adroplet of water and use a pipette tip todrag it over a glass plate covered with asticky polymer. The droplet rolls like aball over the plate, sticking the DNA tothe plate surface. The unravelled DNA canthen be studied under a microscope. Theresearchers described the technique inthe journal ACS Nano (doi:10.1021/nn5063497).

There are two ways to decode DNA:DNA sequencing and DNA mapping. InDNA sequencing, short strings of DNA arestudied to determine the exact order ofnucleotides – the bases A, C, G and T –within a DNA molecule. The methodallows for highly detailed geneticanalysis, but is time- and resource-intensive.

For applications that call for lessdetailed analysis, such as determining ifa given fragment of DNA belongs to avirus or a bacteria, scientists opt for DNAmapping. This method uses the longest

possible DNA fragments to map the DNA’s‘big picture’ structure.

DNA mapping can be used togetherwith fluorescence microscopy to quicklyidentify DNA’s basic characteristics.

In this study, researchers describe animproved version of a DNA mappingtechnique they previously developedcalled fluorocoding.

Chemist Jochem Deen explained: ‘Influorocoding, the DNA is marked with acoloured dye to make it visible under afluorescence microscope. It is theninserted into a droplet of water togetherwith a small amount of acid and placedon a glass plate. The DNA-infused waterdroplet evaporates, leaving behind theoutstretched DNA pattern.’

‘But this deposition technique iscomplicated and does not always producethe long, straightened pieces of DNA thatare ideal for DNA mapping.’

‘Our improved technique combinestwo factors: the natural internal flowdynamics of a water droplet and apolymer called Zeonex that bindsparticularly well to DNA,’ explainedengineer Wouters Sempels.

The ‘rolling droplet’ technique issimple, low-cost and effective.

‘We used a glass platelet covered with

a layer of the polymer Zeonex. Instead ofletting the DNA-injected water dropletdry on the plate, we used a pipette tip todrag it across the plate. The droplet rollslike a ball over the plate, sticking theDNA to the plate’s surface. The strings ofDNA ‘captured’ on the plate in this wayare longer and straighter,’ explainedSempels.

To test the technique’s effectiveness,the researchers applied it to the DNA of avirus whose exact length was alreadyknown. The length of the DNA capturedusing the rolling droplet techniquematched the known length of the virusDNA.

The rolling droplet technique could beeasily applied in a clinical setting toquickly identify DNA features, say theresearchers. The technique couldeventually also be helpful in cancerresearch and diagnosis. ‘KU LEUVEN

Untangling DNA the simple way

Online indexesDid you know that Chemistry in Australia indexes areavailable online? Browse or search our archived backissues from 2003 onwards.

To view the indexes, visit chemaust.raci.org.au and goto Other resources.

iStockphoto/Onur Döngel

research


The natural product epicocconone wasdiscovered by researchers at MacquarieUniversity in 2003 (Bell P.J.L., Karuso P.J. Am. Chem. Soc. 2003, 125, 9304–5).As the first reversible-covalent-latentfluorophore, it has since found widebiotechnological applications inproteomics, live cell imaging and enzymeassays. The masked aldehyde ofepicocconone reacts with amine residues(e.g. lysine) to create a red-fluorescentenamine that is acid-stable but revertsback to the non-fluorescent maskedaldehyde in a base-catalysed reaction,providing a unique ‘turn-on/turn-off’capacity. However, epicocconone suffersfrom photobleaching and a low quantumyield. These challenges inspired theresearchers at Macquarie, along withcollaborators at Rouen University, France,to investigate the design and synthesisof new fluorophores that encompass theadvantages of the natural product butwith improved photophysical properties

(Peixoto P.A., Boulangé A., Ball M.,Naudin B., Alle T., Cosette P., Karuso P.,Franck X. J. Am. Chem. Soc. 2014, 136,15248–56). This group has made the firstapproach to the total synthesis of thenatural product, and concurrently

prepared several analogues that havebetter quantum yields and stability. Thesynthesis is general and straightforward,providing access to libraries offluorophores with long Stokes’ shifts,based on the lead from nature.

A natural fluorophore finessed

Direct oxidative esterification of aliphatic alcohols under mildand base-free conditions is challenging, especially if it is to beachieved using a recyclable catalyst. PhD student Qi Xiao,working with Professor Huaiyong Zhu at the QueenslandUniversity of Technology, has addressed this challenge bydevising a one-pot process for the catalytic transformation ofaliphatic alcohols to the corresponding esters by visible-light

irradiation at ambient temperature (Xiao Q., Liu Z., Bo A.,Zavahir S., Sarina S., Bottle S., Riches J.D., Zhu H.Y. J. Am. Chem. Soc. 2015, 137, 1956–66). The new methodologyuses recyclable heterogeneous photocatalysts comprisinggold−palladium alloy nanoparticles on a phosphate-modifiedhydrotalcite support and molecular oxygen as a benign oxidant.The catalyst effectively couples the basic sites of the supportmaterial with the photocatalytic properties of the alloynanoparticles. Thus, the direct esterification of aliphaticalcohols can be driven without any additives under visible-lightirradiation using benign reaction conditions. Theseheterogeneous catalysts can easily be recycled and reused,which is important in developing practical and cost-effectivecatalytic oxidation processes. This is the first example of ‘green’oxidants and light energy being used to drive direct oxidativeesterification of aliphatic alcohols under mild, base-freeconditions.

Efficient esterification under visible light

May 2015

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Colour control in electron transfer-induced light emissionResearchers from La Trobe andDeakin universities havedemonstrated for the first time theability to finely control the emissioncolour of annihilationelectrochemiluminescence (ECL) inmixtures of luminophores by varyingthe applied potential. AnnihilationECL is the emission that results fromhighly energetic electron transferreactions between electrochemicallyoxidised and reduced precursors. Themany closely spaced redox processesof the mixed systems enable finetuning of the reaction energetics andhence control of the resultingemission colour. The team led byConor Hogan and Paul Francis showedin their recent paper (Kerr E., DoevenE.H., Barbante G.J., Hogan C.F.,

Bower D.J., Donnelly P.S., ConnellT.U., Francis P.S. Chem. Sci. 2015, 6,472–9) that, by using differentcombinations of luminophores andapplied potentials, emission coloursvarying from red to green to blue, aswell as magenta and close to white,could be achieved. These studies arean important step towards thedevelopment of novel voltage-controllable light-emitting devices,and provide interesting fundamentalinsights into electroluminescentsystems. For example, theobservation of efficient HOMO-to-HOMO electron transfer pathways inthese mixed systems sheds light onwhether the reduced or oxidisedpartner becomes the excited state inclassic annihilation ECL experiments.

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The key to exploiting ammonia crackingfor a hydrogen economy is hydrogenrecovery through green approaches.Researchers at the CSIRO led by Dr CherHon (Sam) Lau and Dr Matthew Hill haverecently published unprecedented H2/N2

separation efficiencies of 98% usingpolymer membranes as a green alternativeto energy-intensive separation techniques(Lau C.H., Konstas K., Thornton A.W., LiuA.C.Y., Mudie S., Kennedy D.F., HowardS.C., Hill A.J., Hill M.R. Angew. Chem. Int.Ed. 2015, 54, 2669−73). The key tosuccess is the selective ageing ofpolymers with intrinsic microporosity(PIMs), which reduces nitrogenpermeability over time without sacrificinghigh hydrogen permeability. This isachieved by adding an ultraporousadditive, porous aromatic framework PAF-1,which physically tethers side chains ofthe polymer within its pores to stop thesmallest gas transport pathways taken byhydrogen from closing. The studyadvances membrane use for alternativeenergy production. The CSIRO team isexpanding this study with alternativePIMs for separating other gas pairs.

Like fine wine, gasseparation membranesimprove with age

Living polymerisation catalysed by spinach

Transition metal catalysts have recently been used to achieve spatial andtemporal control of radical polymerisation. But these catalysts are highlytoxic and so the polymers produced require several purification steps beforethey are safe to use. In addition, they are derived from metals that exist intrace amounts in the Earth’s crust and are therefore extremely expensive.Working with Associate Professor Cyrille Boyer at the University of New SouthWales, PhD student Siva Shanmugam has instead used spinach-derivedchlorophyll A, one of nature’s most abundant photocatalysts, to performsustainable green photopolymerisation to produce polymers with myriadpotential biomedical applications (Shanmugam S., Xu J., Boyer C. Chem. Sci.2015, 6, 1341−9). This work harnesses the ability of chlorophyll A to undergophotoinduced electron transfer under light to activate chain-transfer agentssuch as dithioester or trithiocarbonate reagents, which are then able toinitiate and mediate radical polymerisation of a wide range of monomers withexcellent control over molecular weights and molecular weight distributions.

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Bioorthogonal chemistry, or the ability toperform selective chemical reactions in acomplex biological environment, hasrapidly developed into a tool for chemicalbiology. However, its use in disease-targeted pro-drug activation remainslimited. Dr Allan Gamble and co-workersfrom the University of Otago recentlydiscovered a novel method of pro-drugactivation using a bioorthogonal

1,3-dipolar cycloaddition (MatikondaS.S., Orsi D.L., Staudacher V., JenkinsI.A., Fiedler F., Chen J., Gamble A.B. Chem. Sci. 2015, 6, 1212−18). Theapproach involves the use of a strainedtrans-cyclooctene and an azide-functionalised pro-drug, resulting inrapid formation of an unstable 1,2,3-triazoline that undergoes rearrangementto an imine via extrusion of diatomic

nitrogen. The imine is then rapidlyhydrolysed at physiological pH to yieldthe active drug via a spontaneous 1,6-elimination of thep-aminobenzyloxycarbonyl (PABC) linker.Ways to further increase the rate ofcycloaddition and drug release arecurrently being investigated, with theoptimised pro-drugs to be tested in amouse model.

Pro-drug activation using bioorthogonal chemistry

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Surface-oxidised carbon nanotubesare catalystsCarbon-based nanomaterials such as carbon nanotubes havefound significant applications as substrates for supportingmetal and metal oxide nanoparticle catalysts in energy devicessuch as water-splitting cells and fuel cells. Oxygen-containinggroups are omnipresent on the surface of carbon materials, butuntil now their role in catalytic activity has been unclear. Thegroup of Associate Professor Chuan Zhao at the University ofNew South Wales has shown that, upon mild surface oxidation,hydrothermal annealing, and electrochemical activation,multiwall carbon nanotubes (MWCNTs) are themselves effectivewater oxidation catalysts that can initiate oxygen evolution atoverpotentials of only 0.3 V in alkaline media (Lu X., Yim W.-L.,Suryanto B.H.R., Zhao C. J. Am. Chem. Soc. 2015, 137,2901−7). Oxygen-containing functional groups such as ketonicC═O on the outer walls of MWCNTs were found to play a crucialrole in catalysing oxygen evolution by altering the electronicstructure of adjacent carbon atoms and by facilitatingadsorption of reaction intermediates. The well-preservedmicroscopic structure and highly conductive inner walls ofMWCNTs enable efficient transport of electrons generated duringoxygen evolution. These findings open the door to newapplications of surface-oxidised carbon nanomaterials forcatalysing important reactions for electrochemical energystorage and conversion.

Compiled by David Huang MRACI CChem ([email protected]). Thissection showcases the very best research carried out primarily in Australia. RACImembers whose recent work has been published in high impact journals (e.g.Nature, J. Am. Chem. Soc., Angew. Chem. Int. Ed.) are encouraged to contributegeneral summaries, of no more than 200 words, and an image to David.

The April issue is dedicated to the memory of Sir John ‘Kappa’Cornforth, who passed away in December 2013. He was raised inSydney and Armidale and studied chemistry at the University ofSydney, working with Francis Lions and Gordon K. Hughes forhis BSc(Hons) degree. Arthur Birch, later of Birch reductionfame, who was a year ahead of Cornforth at Sydney, hasrecounted in the Historical records of Australian science 2009how Francis Lions used to make cocktails from distilled alcohol,and that ‘his student John Cornforth in about 1938 invented a“cocktail” that contained absolute ethanol flavoured with ethylacetate and vanillin – which effectively smooths down thetissues – coloured by methylene blue [… which] producedchromatic urinary effects after imbibing, dismaying to theuninitiated’. Cornforth was known to make up limericks on therun, and he got his own back on Birch, as reported by SirHarold Kroto in this issue:

That outpost of empire, Australia,Produces some curious mammalia,The kangaroo rat,The bloodsucking bat, and Arthur J. Birch inter alia.

Cornforth subsequently spent all of his scientific life in theUK. Aust. J. Chem. has started a Cornforth Review series in hishonour, and the first such review is published in this issue byL.R. Malins and Richard Payne (University of Sydney) onsynthetic amino acids for applications in peptide ligation–desulfurisation chemistry.

Damon Ridley (formerly of the universities of Sydney andSussex) contributes a foreword with narratives and commentson a number of Cornforth’s publications. Andrew Holmes(University of Melbourne) is the 2015 Cornforth Lecturer at theUniversity of Sydney and reports with several co-workers asynthesis of highly water-soluble adamantyl phosphoinositidederivatives.

Gareth Rowlands of Massey University, New Zealand, and co-workers report an asymmetrical variant of the Bischler–Möhlauindole synthesis.

Martin Banwell and co-workers (ANU) report therearrangement of levoglucosenone, a compound that will soonbe available in tonne quantities through the pyrolysis of acid-treated biomass, to isolevoglucosenone.

Steve Davies (Oxford) and co-workers describe epoxidation oftrans-4-aminocyclohex-2-en-1-ol derivatives, which can takeplace by means of either hydroxyl-directing or ammonium ion-directing pathways. Thus, different ratios of stereoisomers areformed depending on the NRBn substituents as described by thetwo rate constants kN and kO.

Ray M. Carman, Paul V. Bernhardt and Tri T. Le (University ofQueensland) report a highly unusual phenomenon, viz. theformation of a ‘pseudoracemate’; that is a ~70:30 mixture ofdiastereomers instead of the usually expected 1:1 racemate. Thephenomenon is ascribed to a little-known interaction betweenremote chiral centres.

Steven Ley and Sonja Kamptmann (Cambridge University)describe flow chemistry methods resulting in the synthesis of anindole ‘dimer’, which can be converted to the borrerine-derivedalkaloid flinderole A.

Several more papers complete this excellent issue.


Aust J Chem

Curt Wentrup FAA, FRACI CChem ([email protected]),http://uq.edu.au/uqresearchers/researcher/wentrupc.html?uv_category=pub

On November 2014, themultiple manslaughterconvictions of the sixscientists of the Italian

National Commission for the Forecastand Prevention of Major Risks wasoverturned. These scientists and oneex-government official had beenhanded six-year sentences for thedeaths of 309 people in the L’Aquilaearthquake of 2009, the deadliestquake in Italy since 1980.

The conviction itself had leftscientists around the world bothhorrified and alarmed. From one pointof view, it represented a significantescalation in a perceived war onscience and reason that has been

simmering for the last 400 years. Itjoined a chorus of anti-intellectualism,which, like some noxious miasma,pervades societies around the globein forms both overt and perfidious:climate change denial; opposition tovaccination; anti-fluoridation ofmunicipal water supplies; AIDS denial;opposition to the scientific testing ofgenetically modified organisms; and,arguably the grossest moderndebasement of science, ‘intelligentdesign’.

Now, I am not nearly so alarmist.Delving into the L’Aquila case, I foundthat the legal arguments centred noton the fact that the scientists wereincorrect in their predictions, but on


BY DAVE SAMMUT

The L’Aquilaearthquakeconvictions are areminder thatcommunicating riskis a risk in itself.

warofwordsScientists have calculated that the chance of anything so patently absurd as actually existingare millions to one. But magicians have calculated that million-to-one chances crop up ninetimes out of ten.

Terry Pratchett, Mort

iStockphoto/rafal_olechowski

the manner in which their predictionswere communicated. Ultimately, theconvictions were based on theaccused giving ‘inexact, incompleteand contradictory information’ aboutthe dangers of the tremors prior to thequake.

In simple terms, on 5 April 2009 thesix scientists met with a governmentofficial and two local representatives todiscuss a recent series of smalltremors and the alarms raised by alocal lab technician who, reportedly onthe basis of radon levels, predicted animminent quake. They concluded thatthe risk of an earthquake within thenext three days had risen from 1 in200 000 to 1 in 1000 – in other words,unlikely but also significantlyincreased from ‘usual’. The scientistsleft it to the local civil defence officialto speak to a reporter, whoinaccurately reported their findings as‘The scientific community tells us thereis no danger, because there is anongoing discharge of energy. Thesituation looks favourable.’

None of the scientists spoke up tocorrect this statement. In fact, Dr Bernado De Bernadinis,deputy chief of Italy’s CivilProtection Department,added that local citizensshould go and have a glassof wine. The next night, abig quake hit. And this iswhat the trial was about.

Contrast this case to amore recent, andfortunately non-lethal,example – New York’sFebruary 2015‘Nomageddon’. In thiscase, meteorologicalauthorities issued awarning of a major snowfallthat caused the closure ofairports, rail lines and arange of other civicinfrastructure, bringing thecity to a standstill. Yet thethreatened snow fell out tosea, and what had beeninitially forecast as

‘Snowmageddon’ was renamed … tobe followed by widespread publicderision and grovelling apologies fromthe scientists involved.

Both cases come down to the sametwo fundamental principles:uncertainty and risk. Of these,uncertainty lies at the very core ofscience. It is accepted that truescience is measurable, testable andrepeatable. It is honed by detailedscrutiny and repeated challenge, andyet even so it remains open to change.

Even concepts as rigorously testedand thoroughly demonstrable asevolution are only raised to the level of‘theory’ (a term that is widelymisunderstood by non-scientists).Almost no theory ever reaches thelofty peak of becoming a ‘law’, andeven then it is not unassailable.Newton’s laws of motion may form thebasis for a large chunk of modernscience, yet accommodation is stillmade for the contradictory outcomesof quantum theory.

So, uncertainty is critical to thepractice of science. Yet it sitsuncomfortably with the principle of

risk, and this is ultimately what lies atthe centre of many of the ‘debates’listed earlier (except for AIDS denial,which is stupid and reported as such;and intelligent design, where scientificterminology is used without scientificprocess to disguise religiousideology).

Risk is complex. More than just anissue of perception, it embodies boththe chance of an occurrence (positiveor negative) and the effects of thatevent. Acceptable risk variesaccording to the group affected. Theacceptable risk of chemical exposureto a factory worker is different from theacceptable risk for a nearbykindergarten.

Even the language of risk is aproblem. How many of us trulyunderstand what a ‘one in 100 year’flood event risk actually means? As theBureau of Meteorology explains, ‘It isimportant to note that an ARI [averagerecurrence interval] of, say, 100 yearsdoes not mean that the event will onlyoccur once every 100 years. In fact, foreach and every year, there is a 1%chance (a 1 in 100 chance) that the

May 2015

A government office damaged by the 2009 L’Aquila earthquake.

words

Wikim

edia

event … will be equalled or exceeded(once or more than once).’(bit.ly/1DOvji7)

The L’Aquila case ultimately camedown to the perceptions of risk. Lookat the inherent contradiction in thestatement made before the trial by DrVincenzo Vittorini, who lost his wifeand daughter in the quake: ‘Nobodyhere wants to put science in the dock.We all know that the earthquake couldnot have been predicted, and thatevacuation was not an option. All wewanted was clearer information onrisks in order to make our ownchoices.’ He knew that the scientistscouldn’t be certain. He knew thatevacuation was not practical. So what‘clearer information’ would haveenabled him to make his own choices?

Between the ‘scientific community’and ‘the general public’ (both looseterms encompassing quite diversesets of skills and needs) lies a range ofcomplicating stakeholders – media,governments and special interestgroups. Collectively, these complicatethe challenge of communicatingscience effectively to a nearlyinsurmountable extreme.

Of these, I want to particularlyaddress the challenge of the mediaitself. Most critically, the media is abusiness, first and foremost. It thriveson circulation and sensationalism, andits dedication to the truth is peripheralat best.

Setting aside the ideological biasesto reporting underlying particularmajor news networks, the issue of‘balanced reporting’ itself distorts thecommunication of science. Far moreknowledgeable people than me have

commented on the inherent problemin the perceived need in the media topresent ‘both sides’ of a debate,regardless of the scientific merit (orutter lack thereof) of either claim. Callit the difference between the medianand the mean. It gives massivelydisproportionate voice to the fringe,and to special interest groupsmotivated by anything other thanscience.

Consider climate change reporting.Without taking a position on thescience myself, it would be fair to saythat there is a majority consensusregarding the hypothesis ofanthropogenic global climate effects.However, a widely reported paper byM.T. Boykoff and J.M. Boykoff (‘Balanceas bias: global warming and the USprestige press’, Global EnvironmentalChange 2004, vol. 14, pp. 125–36)found that a majority of 636 randomlysampled articles from US mainstreampress gave ‘roughly equal attention’ tothe two ‘sides’ of the discussion, while35% emphasised the consensus viewwhile still presenting the opposition insubordinate fashion, and only 6%focused on the consensus withoutbothering with the other ‘side’.

Just as worryingly, there is anincreasing trend in modern mediatowards the use of ‘sound bites’. Overthe years, science may have had somerare flashes of inspiration in this – think‘Eureka’ (Archimedes), aided forposterity by a naked street run. Butjoking aside, science does not lenditself well to short summaries. It is verydifficult to present findings in ameasured fashion, with due attention touncertainty, in just a few words.

Moreover, our words now haveunprecedented longevity. Hardly aproblem restricted to science alone, itis increasingly common to hearreasoning along the lines of ‘but tenyears ago you said this contradictorystatement’, the corollary being eitherthat the interviewee was or is beinguntruthful, or that whether incorrectthen or now, either way the person canbe universally discounted. Obviously,this directly contradicts the very basisof good science.

In this context, the initial L’Aquilaconviction is of concern – that the legalsystem is increasingly backing apublic perception requiring scientiststo not only do their jobs, but also takeliability for the understanding ofaudiences outside the profession. Thishas the potential to gag scientists fromthe proper participation in publicdiscussion of scientific issues.

As Stuart Clark noted in TheGuardian after the 2012 conviction(bit.ly/17Tf2j9):

In 1633, the punitive treatment of Galileoeviscerated the practice of astronomy inItaly for centuries … although theconviction was for miscommunication,astronomy itself became toxic ...

Today, it is very hard to see how theconviction of these geologists will doanything to improve the sciences in Italy.Certainly, lessons in the communicationof earthquake risk must be learned …but who will dare to speak up now withthis outcome as precedent?

Ultimately, there is no simpleanswer to this problem. However, thereis one emerging solution underwaythat I believe should help – theincreasing inclusion of media andcommunications training inundergraduate science degrees,particularly at institutions in the UK.The better we understand the needsand approaches of the audiences withwhom we are communicating, thebetter prepared we will be to do so.

Dave Sammut FRACI CChem is principal of DCSTechnical, a boutique scientific consultancy,providing services to the Australian and internationalminerals, waste recycling and general scientificindustries.


Between the ‘scientific community’ and ‘thegeneral public’ ... lies a range of complicatingstakeholders – media, governments and specialinterest groups. Collectively, these complicatethe challenge of communicating scienceeffectively to a nearly insurmountable extreme.

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2015 media guidenow available

iStockphoto/Jirkab

The discovery of theconductive properties oforganic materials has led tothe expanding field of

organic electronic devices andconductive polymers. Organic light-emitting diodes (OLEDs), photovoltaicsand dye-sensitised solar cells arecomponents of everyday items such asmobile phone and television displaysand rooftop solar systems forelectricity generation. Globally, thevalue of this market is predicted togrow from over $16 billion in 2014 tomore than $75 billion by 2020(bit.ly/1Fvz8uG).

Development of new organicmolecules with tailoredelectrochemical properties isattracting significant attention. Onemechanism under investigation is thereplacement of hydrogen (1H) withdeuterium (2H, or D) within the organicmolecules in these devices. It is oftenassumed that this isotopic substitution

does not significantly change thechemical and optoelectronicproperties of the parent compound,but the relatively large mass differencebetween hydrogen and deuterium canresult in different behaviours ofdeuterated molecules from that of theirprotonated analogues.

This difference has been observedin optical fibres. They transmit lightalong a length of filament by multipleinternal reflections of light. It isimportant that the light applied at oneend of the filament is efficientlytransmitted to the opposite end, so it isnecessary to minimise light losses dueto absorption and scattering. Thetransmitted light is often (unfavourably)attenuated by the C–H bond vibrationsof the organic molecules used toconstruct the polymeric core of thefibre. Deuteration of these organicmolecules eliminates the C–H bondvibration, reducing light losses alongthe transmission.

Deuteration of conducting polymershas been reported to alter theoptoelectronic properties of themolecules and the resultant processes(such as charge transport) inphotovoltaic devices (Nature Mater.,doi: 10.1038/nmat2633; NatureCommun., doi: 10.1038/ncomms4180).Deuteration of organic moleculeswithin the emissive layer of OLEDs hasimproved features such as light-emitting efficiency, high-voltagestability and device lifetime (J. Phys.Chem. C, doi: 10.1021/jp066116k).

Deuterated molecules can besynthesised in a variety of ways, basedon either chemical or biologicaldeuteration.

Chemical deuterationSeveral methods can be used toperform hydrogen/deuterium-exchange reactions at carbon centres,including pH-dependent exchangeand exchange catalysed by either a


Heavyhydrogen

Making the mostof conductive molecules

homogeneous catalyst (such as Pd orPt salts, e.g. K2PtCl4) or aheterogeneous catalyst (such as Pt/Cor Pd/C). The source of deuterium forexchange is often D2O, but thesereactions can also be performed usingD2 gas or deuterated protic solvents toprovide labile deuterium atoms. Hightemperatures and pressures are alsooften necessary to achieve high levelsof deuterium incorporation, requiringexpensive specialised hydrothermalvessels (see photo p. 22).

Often, a desired molecule cannotbe deuterated directly, because offactors such as insolubility, volatility,instability at high temperature andincompatibility of functional groupswith the catalyst and/or reaction vessel.Instead, the synthesis of the desireddeuterated molecule can require thedeuteration of precursors andassembly via standard organicchemistry methodology.

BiodeuterationAnother method for producingdeuterated molecules isbiodeuteration. Microbial cultures(such as E. coli or algae) are grown inD2O and supplied with eitherdeuterated or hydrogenated ‘food’,depending on the level of deuterationrequired. The desired deuteratedmolecule (such as proteins, lipids,nucleic acids or polysaccharides) isthen extracted from the biomass andpurified by standard biochemicaltechniques.

Synthesis of deuterated OLEDcompoundsTCTA (tris(4-carbazoyl-9-ylphenyl)-amine) protein (utilised in holetransport layers) is one compound thathas been deuterated for use in OLEDdevices. The synthesis of deuterated

TCTA via H/D hydrothermal exchangein D2O directly on protonated TCTAresulted in low yields and relativelylow overall deuterium incorporation.This was despite the addition of THFas a co-solvent to improve thesolubility of the compound in D2O tofacilitate the H/D exchange. Instead,the carbazole precursor was firstdeuterated under hydrothermalconditions in D2O catalysed by Pt/C,and then reacted with protonatedtris(4-bromophenyl)-amine via amodified Ullman condensation (seescheme p. 24) to synthesisedeuterated TCTA (Tetrahedron Lett.,doi: 10.1016/j.tetlet.2011.12.032).

Organic chemists at the NationalDeuteration Facility (NDF) haverecently developed a method thatutilises mild reaction temperatures(80°C) and standard laboratoryglassware for the large-scale (tens ofgrams) deuteration of primary andsecondary arylamines, such as N-phenylnaphthylamine andN-phenyl-o-phenylenediamine. Thismethod eliminates the requirement for

the expensive, specialisedhydrothermal vessels for the bulksynthesis of these molecules. Thesedeuterated precursors can then beused for the assembly of deuteratedorganic molecules (such as NPD andTPBI, see diagram on p. 24) for use inoptoelectronic devices, as directdeuteration of these final compoundsis also not favourable. Thedevelopment of these mild conditionsand the large-scale synthetic methodcan allow for synthesis of deuteratedmolecules with optoelectronicapplications on a larger scale, which


OLEDs are multiple organic layerssandwiched between two electrodes.Typically, an OLED electron transport layercontains electron deficient molecules, thehole transport layer contains electron-richmolecules, with the molecule(s) for theemissive layer selected on the basis ofdesired colour of the device and oftenblended with a host.

BY ANWEN KRAUSE-HEUER

Molecular deuteration is making its markin the expanding field of optoelectronics.

Mass spectrum of deuteratedNPD, showing the distribution ofthe deuterated isotopologues.

may be of benefit for commercialapplications.

Characterisation of deuteratedmoleculesIt is important to be able to calculatethe overall efficiency of deuteration inthe final organic molecule; for neutronstudies, this allows the scatteringlength density of the material to beestimated. The overall levels ofdeuterium incorporation aredetermined by mass spectrometry(MS), as each additional deuteriumatom incorporated into the moleculeincreases the mass of the molecule byone mass unit. The percentagedeuteration can be calculated byanalysing the area under eachcorresponding isotopologue, taking

into account the percentagecontribution of the 13C isotopicdistribution. The example massspectrum of deuterated NPD (p. 23)shows the distribution of theisotopologues.

Nuclear magnetic resonance (NMR)spectroscopy can be used as acomplementary technique to MS tocalculate the percentage ofdeuteration. The deuterium nucleushas a spin quantum number of 1,making it NMR silent in 1H NMRspectroscopy. By adding an internalstandard with a known number ofmoles of protons, and comparing theintegration of the resonance of theinternal standard to the resonances ofthe residual protons (as the deuteratedsites are NMR silent), it is possible to


OLED precursors (carbazole, N-phenylnaphthylamine and N-phenyl-o-phenylenediamine) can be deuterated via H/D exchange in D2O, and then thefinal deuterated OLED molecules (TCTA, NPD and TPBI) be assembled viastandard organic chemistry techniques.

The replacementof hydrogen withdeuterium canalter and improvethe optoelectronicproperties of themolecule, andallow thefunctional devicesto be studied vianeutron scatteringtechniques.

calculate the number of moles ofresidual protons in the sample.Integration of individual resonancescan also indicate the amount ofdeuteration incorporation at specificsites.

In addition to aromatic moleculesfor optoelectronic devices, the NDF isable to synthesise a wide variety ofdeuterated molecules, for a variety ofapplications, including deuterated fattyacids, lipids, phospholipids, sugarsand surfactants. Many of thesemolecules are particularly useful forinvestigations of biological systemsthat can be studied by neutronreflectometry and small-angle neutronscattering (SANS).

Deuteration for neutron studiesAs well as potentially improvingperformance of OLED devices,deuteration allows devices to bestudied by neutron beam instruments,such as those at ANSTO’s BraggInstitute.

Researchers from the University ofQueensland have utilised the Platypusneutron reflectometer at the BraggInstitute to investigate the buriedinterfaces within functioning OLEDdevices.

During a neutron experiment, theneutrons directed at a sample interactwith and are scattered by the nuclei

they encounter. The various nucleiinteract differently with neutrons; themeasurement of this interaction isknown as the scattering length. 1H (0.3742 × 10–12 cm) and 2H(0.6671 × 10–12 cm) have very differentscattering lengths; this difference canbe exploited during a neutron beamexperiment to highlight and studyparticular components of a system.The NDF synthesised deuteratedmolecules for incorporation intofunctioning OLED devices, as selectedcombinations of protonated anddeuterated components providescattering contrast between the layers,allowing analysis and measurements ofthe individual layers.

These experiments revealedinformation about the thermal stressesexperienced by the layers andmaterials found in typicalphotoluminescent OLED devices. Atincreased temperatures (90–100°C),two of the individual layers began todiffuse into one another. This wasmade apparent by the use ofalternating protonated/deuteratedlayers, which showed changes in thescattering length density across thedevice thickness as the protonated anddeuterated materials began to diffuseinto one another at the interface (Adv.Mater., doi: 10.1002/adma.201104029;Adv. Funct. Mater., doi: 10.1002/

adfm.201002365). This diffusionresulted in changes to the chargetransport behaviour of the device anda subsequent degradation inperformance.

Further applications andunderstandingOrganic electronic devices alreadyfeature prominently in many aspects ofour lives, and this will likely onlycontinue to increase. In order tocontinue to improve the performanceand push the boundaries in theapplications of these devices, newmolecules may be required, along witha greater understanding of how thesedevices work. The deuteration oforganic molecules for optoelectronicapplications can assist in achievingboth of these outcomes. Thereplacement of hydrogen withdeuterium can alter and improve theoptoelectronic properties of themolecule, and allow the functionaldevices to be studied via neutronscattering techniques. The beneficialfeatures imparted by deuteration mayalso be applied to many other fields ofchemistry, physics and biology.

Dr Anwen Krause-Heuer MRACI is an organicsynthetic chemist at the Bragg Institute, AustralianNuclear Science and Technology Organisation.


National Deuteration Facility The NDF was established in 2007 and is jointly funded by theNational Collaborative Research Infrastructure Strategy (NCRIS)and the Australian Nuclear Science and Technology Organisation(ANSTO). The NDF primarily provides deuterated molecules to beused for experiments within the Bragg Institute that use neutronsgenerated by ANSTO’s nuclear reactor, OPAL.

Access to the OPAL Neutron Beam Facility and the NDF for non-proprietary research is via a peer-reviewed merit based proposalsystem, with more information available at www.ansto.gov.au/ResearchHub/Bragg/Facilities/NationalDeuterationFacility.

A view of the neutron guide hall atthe Bragg Institute, ANSTO.

The increasing number ofterrorist attacks hasgenerated considerableconcern throughout the

world. Not only do explosive devicesused in terrorist attacks result inmultiple deaths and casualties, theycan also cause the collapse ofbuildings, bridges and other importantinfrastructure.

When a bomb is detonated outsidea building, it releases a huge amountof energy instantaneously. Theresulting shock wave in thesurrounding air expands rapidly to thefront of the building, blowing itsexterior walls and columns. The blastpressure inside the building movesfloors upwards while the blastpressure on the outside of the buildingforces the side walls, roof and rearwalls inwards.

The direct air-blast effects causelocal failure of parts of the building.Flying debris generated from thedirect blast causes further damage tothe building and injury to its

occupants. Local failure may progressto global failure and the collapse of thebuilding.

To enhance the resistance ofstructures to both local and globalfailure due to an explosion, there hasbeen a significant increase in boththeoretical and experimental researchinto the behaviour of structuralcomponents subjected to blastloading. The major objective is toincrease the energy dissipationcapabilities of the structuralcomponents, with most of the focus ondeveloping new materials to absorbblast energy.

In order to improve the capacity ofbuilding materials to absorb the high-energy impacts of bomb blasts, we aredeveloping an ‘ultra-high performanceconcrete’ (UHPC) that substantiallyimproves the mechanical propertiesand plasticity of hardened concrete.We are currently developing andtesting new materials that incorporatenanoscale materials into steel fibre-reinforced self-compacting concrete.


Bomb-proofing

buildingsBY

CHENGQING WU

A new form ofreinforced concretethat can absorb theblast of an explosionis being developedfor use in buildingsthat can withstandterrorist attacks.

The steel fibres not only increase theconcrete’s plasticity and tensilestrength – the ability to withstandstretching or pulling – they also createa homogeneous mix that binds cracksand retards their propagation, thuspreventing sudden compressivefailure.

What is ultra-high performanceconcrete?Ultra-high performance concrete is amix of self-compacting concrete with1–3% steel or synthetic fibres byvolume. With low water to bindercontent and much smaller particlesize, the self-compacting concrete isknown for its high ‘flowability’ andgood cohesiveness.

Combining self-compactingconcrete with end-hooked, waved andspiral steel fibres can enhanceanchorage properties within thesurrounding structure and significantly

improve its performance. The furtheraddition of nanoparticles of CaCO3,SiO2 and Al2O3 facilitate chemicalreactions that can be used to improvethe performance of UHPC.

Immediately after the mixingprocedure, slumps of the freshconcrete are measured to ensure thatthe consistency and flowability of theUHPC is suitable for constructionpurposes.

Improved blast resistanceTests with our Chinese collaborators atTianjin Chengjian University havefound that structural componentsmade from UHPC have a greaterability to withstand the effects of blasts.The material is at least five timesstronger than conventional concrete,with five times the ability to withstandcompression, 10 times the tensilestrength and improved plasticity.Furthermore, the energy dissipation


Damage to the US Embassy, Beirut, caused by a terrorist bomb attack in 1983.US Army/Wikimedia

The steel fibres notonly increase theconcrete’s plasticityand tensile strength– the ability towithstandstretching or pulling– they also create ahomogeneous mixthat binds cracksand retards theirpropagation, thuspreventing suddencompressivefailure.


A new type of steel-reinforced concrete protects buildingsbetter from bomb attacks. Researchers have developed aformula to quickly calculate the concrete’s required thickness.The material is being used in the One World Trade Center atGround Zero.

Earthquakes and explosions produce tremendous forces.Pressures in the immediate vicinity of a car bomb are in therange of several thousand megapascals, and even furtheraway from the detonation itself, pressures are still in theorder of several hundred kilopascals. Pressure in a bicycle tyre– at about three bar – corresponds to about 300 kilopascals.‘So people at a good distance from the detonation point arenot so much endangered by a pressure wave – our bodies canusually cope pretty well with them – it’s flying debris thatposes the real danger,’ explained Dr Alexander Stolz from theSafety Technology and Protective Structures department at

the Fraunhofer Institute for High Speed Dynamics, ErnstMach-Institut, EMI in Efringen-Kirchener, just north of Baselin Germany. This is exactly what happens to conventionalreinforced concrete when it is hit by an explosion’s pressurewave: it is so brittle that individual and often large pieces aretorn off and fly through the air uncontrolled.

Dr Stephan Hauser, managing director of DUCON EuropeGmbH & CoKG, has developed a concrete that merely deformswhen subjected to such pressures – and doesn’t break. Behindthe development is a special mixture made from very hardhigh-performance concrete, combined with finely meshedreinforced steel. The EMI has been supporting Hauser formany years in the optimisation of his patented innovation. In particular, the researchers take responsibility for dynamicqualification testing of the material under extreme loads. Thisalso involves characterising the material and calculatingcharacteristic curve profiles. The researchers have developed amathematical formula that simply and quickly computes therequired thickness of the new concrete for each specificapplication.

‘Calculations used to be based on comparable andhistorical values,’ said Stolz. ‘Now we can use a universalalgorithm.’

The formula was developed during a test series with thenew shock tube in Efringen-Kirchen.

‘We can simulate detonations of different blasting forces –from 100 to 2500 kilograms TNT at distances from 35 to50 metres from buildings. And that’s without even having touse explosives,’ said Stolz.

The principle behind it is this: the shock tube consists of a(high-pressure) driver section and a (low-pressure) drivensection, which are separated by a steel diaphragm. Air can becompressed in the driver section to a pressure of up to 30 bar,i.e. to approximately 30 times atmospheric pressure at sealevel. The steel diaphragm is ruptured when the desired levelof pressure is reached: the air is forced through the drivensection as a uniform shock front that hits the concretesample being tested, attached to the end of the shock tube.

‘With conventional concrete, the impact pressure rippedout parts of the sample concrete wall, which failed almostinstantly, while the ductile and more flexible security versionof the concrete merely deformed. There was no debris, andthe material remained intact,’ said Stolz.

Thanks to its ductile qualities, the security concrete isconsiderably less bulky and yet more stable than conventionalsteel-reinforced concrete. Thinner building components arepossible.

‘As a rule of thumb, you get the same stability with halfthe thickness,’ said Stolz.FRAUNHOFER

The One World Trade Center at Ground Zero rests on a 20-storey,bombproof foundation that reaches 60metres underground.Overall, at points within the building where safety is especiallycritical, several thousand square metres of safety concrete havebeen used to shore up the construction.

Formula calculates thickness of bombproof concrete


capabilities of the UHPC structuralcomponents can be several orders ofmagnitude higher than normalconcrete materials.

Full-scale blast tests have also beenconducted to investigate the resistanceof UHPC columns to nearbyexplosions. In order to resist this blastloading and minimise structuraldamage, the concrete column must be

able to absorb or dissipate the energy. Our blast tests revealed that while a

conventional reinforced concretecolumn failed to withstand a 10 kgexplosive, the new UHPC columncould survive a 50 kg explosive. Thisindicates that columns made of thenew UHPC materials are strongenough to prevent the collapse ofbuildings after terrorist attacks made

with devices such as contact suitcasebombs and nearby car bombs.

UHPC therefore has tremendouspotential for use in high-rise buildings,bridges and other infrastructure underthreat of seismic, impact and blastloads.

Ongoing researchAll military and buildings that may bea target should be designed forreduced vulnerability against terroristattack. The superior strength andplasticity of UHPC make it an idealmaterial for these engineeringchallenges. The new UHPC we havedeveloped has great potential for usein the design of future blast-resistantstructures and ultimately to thedevelopment of blast-mitigatingtechnologies.

Our research team has alreadycarried out an extensive investigation,and both finite element analysis andblast-testing techniques have beenused to study the characteristics ofUHPC under different loadingconditions. The results will help usdevise guidelines for using the newmaterial in building designs.

The price of the new concrete isabout five times that of conventionalconcrete, which is currently prohibitivefor widescale use. However, we areworking to improve the cost-effectiveness of the formula.

If costs can be reduced to enable itswidespread use, there is no doubt thatthe new UHPC can help strengthenAustralia’s defence and nationalinfrastructure engineering capabilitiesand help safeguard against terroristattacks.

Chengqing Wu is a senior lecturer in the Universityof Adelaide’s School of Civil, Environmental andMining Engineering. He is also the Director of theTCU-UA Joint Research Centre on Disaster Preventionand Mitigation, and chairs the Australian Chapter ofthe International Association of ProtectiveStructures.

First published in Australasian Science(www.australasianscience.com.au).

The horizontal spread of UHPC concrete reinforce with steel fibres (left) is comparable withconventional concrete (right). Keeping the horizontal spread consistent is necessary toendure the quality and workability of UHPC.

Top: This reinforced concrete column failed under a 10kg explosive load. Bottom: The UHPC columns maintained their structural integrity after a 50kg explosive load.

raci news obituary


David Wood, past-president of the RACI, has been awarded anhonorary doctorate by the University of Melbourne, of which he is Emeritus Professor and Professorial Fellow. The doctorate waspresented on David’s birthday in December 2014 at the RoyalExhibition Building in Melbourne.

David joined the Department of Chemical Engineering in the1960s as a lecturer, progressing to Head of Chemical Engineeringand then to Dean of the Engineering Faculty. Also, in addition tohis academic work, he has been very involved in outsideactivities. In his view, ‘lucky people like me should give back tosociety what they have gained in terms of good opportunitiesand education’.

In the late 1970s, David initiated a proposal to completelyoverhaul the superannuation scheme for Australian universitystaff. He was active in the staff union and one day he put hishand up and ‘the rest is history’. The end result was UniSuper.

Over many years, David has played significant roles,including Vice-President, Worldwide, of the Institution ofChemical Engineers. He has edited some of its journals, chairedmany of its committees and worked hard to establish theAustralian presence. He has received a number of awards fromthe IChemE, including the CHEMECA Medal in 2001. Thisfollowed the outstanding Sixth World Congress of ChemicalEngineering, which he chaired. He was determined to show thatAustralia could showcase chemical engineering in this countryto the rest of the world. He founded and eventually chaired theWorld Council of Chemical Engineering, which aims to improvethe outreach of chemical engineering throughout the world.

David has been an active member of the RACI, including asPresident, as one of the organisers of the International Year ofChemistry activities and as chair of the Chemistry in Australiamanagement committee.

David described his past 10 years working (in an unpaidcapacity) in China for nine universities as ‘the most satisfying’,including his appointment as an Honorary Professor at TianjinUniversity.

In his citation, David is described as ‘a committed andpassionate chemical engineering professional, a leader andeducator who has made significant contributions to both thisuniversity and the profession of chemical engineering as awhole’. David said his work at the University of Melbourne hasbeen most enjoyable and he is very honoured to have beengiven the opportunity to work there. ‘By world standards it isreally a great university and I have had the chance to teachbrilliant students and to undertake enjoyable research.’

As David was presented with the award in the presence ofmany new graduates, faculty members and his family and friendshe reflected on ‘the great fortune that I have had to have beengiven the opportunity to participate in a great university, a greatprofession (chemistry and chemical engineering) and to havesome wonderful friends and associates’.

Honorary doctorate for David Wood


raci news obituary

Graeme Richard Hanson was born inMelbourne on 16 July 1955. Heattended local state schools andgained entry to La Trobe Universityto study science, completing a BScwith Honours in 1978. His Honoursresearch and thesis showed thehallmarks of tenacity andapplication that were to typify hisscientific life. The work was

continued at La Trobe into his PhD, and it was during theseformative years that Graeme was introduced to the technique,the research area and the people who influenced his researchand led to the establishment of his scientific reputation. Thattechnique was electron paramagnetic resonance (EPR)spectroscopy, the research area was bioinorganic chemistry andthe people were Tony Wedd, John Pilbrow and Keith Murray.

After leaving La Trobe, Graeme moved to the Harvard MedicalSchool with Professor Bert Vallee, where he was involved withEPR characterisation of the inhibitor complexes of cobaltcarboxypeptidase A. From there he moved to Monash University,joining John Pilbrow and Keith Murray, and then to theChemistry Department at the University of Queensland, wherehis interest in the marine cyclic peptides began. He then movedto the then Centre for Magnetic Resonance to establish the EPRfacility, under the directorship of David Doddrell. Graemeestablished, promoted and developed the facility with all thetenacity and perseverance that typified everything he did.Graeme’s reputation in the field of EPR grew, both nationallyand internationally.

At the time of his passing, Graeme was a professorialresearch fellow (promoted in 2002) and the Head of the EPRGroup at the Centre for Advanced Imaging at the University ofQueensland. He was an honorary professor in the School of Lifeand Environmental Sciences at Deakin University in Victoria, aFellow of the RACI and Treasurer of the Society of BiologicalInorganic Chemistry.

One of the many important scientific contributions Graememade was to establish EPR spectroscopy as an essential tool forelectronic structure analysis of paramagnetic compounds and forthe correlation of electronic structure with geometry. His deepunderstanding of the physics of metal complexes and electronspin and the mathematics to describe these phenomena led tothe development of the Sophe suite of programs to simulateEPR spectra, a program package unique in its power andversatility. For Graeme, careful planning and thorough

discussions with collaborators and the optimisation of theexperiment to get the highest possible quality of data wereimportant, coupled with an insistence on a consistentinterpretation of the data. He could see things in a spectrumand interpret what he saw with an uncanny skill, and no paperwas complete until those interpretations and simulations weredone.

Graeme contributed to the development of the BiologicalInorganic Chemistry community. He served as the Treasurer forthe Society of Biological Inorganic Chemistry (SBIC) for twoconsecutive terms. He served as Treasurer of ANZMAG, theAustralian and New Zealand Society for Magnetic Resonance. In 2003, Graeme was co-chair (with Tony Wedd and TrevorHambley) of the 11th International Biological InorganicChemistry Conference held in Cairns. As late as December lastyear Graeme was instrumental in the success of the AsianBiological Inorganic Chemistry Conference (AsBIC7) held on theGold Coast, which he co-chaired with Sue Berners-Price.

A common theme in the messages from the internationalcommunity and former students is the description of Graeme asa kind-hearted person. He was committed to supporting thenext generation of scientists and worked hard to secure travelbursaries for students attending AsBIC7 and established theAsBIC Early Career Awards.

Graeme took a keen interest in soccer and his sons playedthe game at various clubs around Brisbane and he was usuallyinvolved in some capacity. He was President of the MoggillFootball Club in outer Brisbane for a number of years. He waseither coach or manager of various teams over the last 11 yearsor so and coached his team to victory several times at theRegional Futsal Championships held in Brisbane each Easter.

Graeme had an enormous influence on the people aroundhim, especially students. From him we all learnt the value ofperseverance, thoroughness and pursuit of the answer. Just ashis family, his wife Lyn, children Jeff, Harry, Joanne and Adrian,will miss him, so will the scientific community. To quote from acolleague: ‘Graeme was a great man, a wonderful personality,very special, modest, gentle, supportive and patient, and agreat scientist, very thoughtful, thorough, sincere, and restlessin his search for answers. He lived in his own world, in themiddle of a wonderful family, the international EPR society andthe bioinorganic community. Graeme had a special humour, hisway to enjoy life, he was a happy man.’

Lawrence Gahan FRACI CChem (with Sue Berners-Price FRACI CChem, PeterComba MRACI CChem and Tony Wedd FRACI CChem)

Graeme HansonElectron paramagnetic resonance innovator

books

My brief history: a memoirHawking S., Bantam Press, 2013,hardback, 127 pp., ISBN9780593072523, $25 approx.Stephen Hawking must surely be oneof the most widely recognisedpeople on Earth. His frailwheelchair-bound body, whichentraps one of the most brilliantminds of our age, evokes pity,wonder and awe that somebodywhom life has dealt such a poorhand should have become one ofthe world’s greatest theoreticalphysicists and cosmologists.

Hawking’s most famous book is A brief history of time. It’sprobably true to say that a lot more people have started it thanfinished it. Complex stuff! By contrast My brief history is briefby title and content, I suspect both for marketing reasons(playing on the word ‘brief’) and because, for Stephen Hawking,the actual writing task is horrendously difficult. His memoir iseasy reading (I polished it off over a couple of nights in bed)and recommended for a general readership.

The book is dedicated to Hawking’s three children and is,accordingly, a personal family memoir. It’s astonishing to learn,for example, that the Lucasian Professor of Mathematics atCambridge University, a Chair once held by Isaac Newton,concluded his formal study of mathematics when he finishedschool in St Albans. The rest of what he needed he just pickedup subsequently, along the way. Hawking’s father, a researcherin tropical medicine, counselled there was no future inmathematics (he could only become a teacher!) and rather heshould direct his efforts towards chemistry. The young Hawking,somewhat surprised to be accepted as a student by Oxford,entered enthusiastically into the prevailing Oxford ethos of hisset that study and hard work were all just a tad boring.Consequently he did so little work (he calculated he did lessthan one hour per day over the course of his degree!) that hisacademic fate required fronting a board to see whether hedeserved a First or a Second – should he go on to a researchcareer or be damned to a life in the civil service. Fortunately,the cards fell the right way and he went on to Cambridge to doresearch.

Hawking wanted to work for his doctorate with Fred Hoyle,the arch-proponent of the theory of a steady-state universe.Given Hawking’s pivotal role in the Big Bang theory, it wasfortuitous that Hoyle was too busy to take him on as a studentand Hawking worked instead with the much more accessibleDennis Sciama. At about this time, the early 1960s, the youngHawking (born 1942) married and became aware of his

diagnosis with motor neurone disease. Given his gloomyprognosis, Hawking could well have given up and accepted hisseemingly imminent demise. As subsequent events confirm, hedid not. The story of his life is inspirational, of magnificentcourage against his major health problems, driven by anamazing will to not let his handicaps hold him back, but to dowhat he can and not get too worried about what he can’t.

The last chapter of the book, ‘No Boundaries’, is mostinspirational. Without boasting, Hawking notes some of theachievements accomplished since he acquired motor neuronedisease aged 21. To quote him, ‘I have had a full and satisfyinglife. I believe that disabled people should concentrate onthings that their handicap doesn’t prevent them from doing andnot regret those they can’t do. In my case, I have managed todo most things I wanted.’ He has travelled the world, visitingevery continent except Australia (but including Antarctica); hehas lectured in the Great Hall of the People in Beijing and inthe White House; he has been down in a submarine and up in ahot air balloon; he has been up in the ‘vomit comet’ andexperienced zero gravity; and he anchored the ParalympicGames in 2012. He has been feted by presidents andpotentates. He’s twice been married and has three children, oneof whom (Lucy) he co-authors children’s books with. Not toomany folk, able bodied or no, can claim such loftyachievements. In passing, Hawking mentions that he’s not yetwon a Nobel Prize (though he has won the more valuableFundamental Physics Prize). Well, I guess he’s in good companythere, at least with the first bit!

I thoroughly enjoyed this book; indeed I found it quiteinspirational. It gives interesting insights into Stephen Hawkingthe fellow human being as distinct from Stephen Hawking theutterly dependant genius in a wheelchair. It made me realisehow lucky I am, but also just how wonderful the human brainreally is when it isn’t cluttered with the everyday trivia of dailylife. Take away all the dross of daily existence and, like StephenHawking, you can truly think. Who knows what we might all becapable of? But of course, I don’t envy his situation.

R. John Casey FRACI CChem


PTYLTDRowe Scientific

www.rowe.com.au

ADELAIDE08 8186 [email protected] BRISBANE07 3376 [email protected] HOBART03 6272 [email protected] MELBOURNE 03 9701 [email protected] PERTH08 9302 [email protected] SYDNEY02 9603 [email protected]

Pledge to Chemists

This is not a “subtle” attempt to obtain more

R.J. Rowe (FRACI)

‘Every-Prac’ HSC Chemistry: videodemonstrations and explanations ofevery practical in the (NSW) HSCsyllabus

Ticli P., Eucalyptus Media Ltd, 2014Part 1: Production of materials, ISBN 9780992400613, $4.99Part 2: The acidic environment, ISBN 9780992400620, $4.99Part 3: Chemical monitoring andmanagement, ISBN 9780992400637,$4.99

As the title ‘Every-Prac’ HSC Chemistrysuggests, this interactive series ofthree e-books demonstratesexperiments of the New South Waleshigh school chemistry course corecontent and is a useful resource forreview by students in years 11 and12. It could also serve as a usefullaboratory manual as a studentprogresses through their course. Someexperiments may be useful as ateacher resource where access tochemicals and/or equipment islimited, for example the preparationof bromine (Part 1) to show itsdifferent reactivity in addition andsubstitution reactions.

Ticli’s books are named accordingto the modules of the textbookConquering chemistry HSC course(Roland Smith, McGraw Hill, 4th edn,2006). This NSW syllabus-basedtextbook is commonly usedthroughout high schools. The modulesbecome the names of the ‘Every-Prac’series, for example Module 1 ‘TheProduction of Materials’ pairs withPart 1 of Ticli’s e-book titled‘Production of Materials’. Even thoughthe material is NSW-centric, thecontent is universal to chemistry

study and would have utility for teachers and students in otherparts of Australia.

All experiments are filmed in the teaching laboratory, whichadds authenticity and familiarity for students. The presentationstyle is relaxed and simple terminology is incorporated in thediscussions. The video clips are on average about six minuteseach; the shortest is three minutes while the longest is morelike 15 minutes. Overall there are 39 videos, either a movie ofthe experiment being performed or a screencast explanation.

In total, the series comprises 62 pages. The book’sorganisation is ‘practical’; each topic starts off by identifyingkey points, which are then matched to syllabus dot points. Asummary of results and calculations (if required) follows eachvideo, and a review section consisting of multiple-choicequestions is included at the end of each part of the series.

These e-books represent a review of experiments previouslycovered in class. While the syllabus requires students to planexperiments, select appropriate equipment and relay MSDSinformation, there’s no opportunity to demonstrate thesequalities throughout this series. The addition of extensionwork/experiments at the end of a topic or in the review sectionwould address this aspect. Repetitive utterances (e.g. ‘aaah’)during some video dialogue detracts from what is otherwisegood work. The series would also have benefitted from tighterediting to remove more typing and grammatical errors andcorrect a few minor technical faults (e.g. NTP occurs at 20°Crather than 24°C).

Overall ‘Every-Prac’ HSC Chemistry closely complements theNSW high school chemistry syllabus, would serve as a usefulteaching aid in the laboratory and achieves its intendedpurpose – namely a medium for the review of all experiments bystudents as they prepare for final exams.

According to Facebook posts, Ticli appears to be well likedby his students. This author has also produced and writtenthree religious-based Kindle books – Moral-i-Tales: The cove andThe magic puppet, and Yosemite – a spiritual journey. He studiedphysiotherapy at the University of Sydney and 13 years latercompleted his Diploma of Education. He also holds a Mastersdegree in theology.

Alison McKenzie


John Wiley & Sons books are now available to RACI members at a20% discount. Log in to the members area of the RACI website,register on the Wiley Landing Page, in the Members Benefits area,search and buy. Your 20% discount will be applied to yourpurchase at the end of the process.

Receive 25% off Elsevier books at www.store.elsevier.com (usepromotion code PBTY15).

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Call 1300 853 352 or visit www.memberadvantage.com.au/raci

It started as a comment over coffee at RMIT University’s citycampus. While discussing possible joint projects with Agilentfor the coming year, I’d mentioned that I was shortly headingto a metabolomics conference in Singapore. Tom Hennessy fromAgilent suddenly spoke up: ‘We make all our LC-MS instrumentsin Singapore; I can arrange a visit to the factory for you if youlike’.

For an analytical chemist like me, being offered a chancesuch as this is somewhat akin to being offered a private tour ofWilly Wonka’s chocolate factory, so naturally I accepted.

Two months later I found myself in a taxi, heading awayfrom the glitz and shiny towers of the southern part ofSingapore island towards the more industrialised north.

The Agilent facility sits within the Yishun industrial estate(bit.ly/1F7cRmK), only a stone’s throw away from the Strait ofJohor, which separates Singapore from Malaysia. From theoutside, the only real clue to the building’s identity is theAgilent logo high up on one of the walls. Just like Wonka’sfactory, however, the real magic happens on the inside.

Once inside, I was met by Saw Wan-Koon (LC-MS FacilityManager), Caleb Ng (South East Asia Life Science CountryManager) and Low Sui-Ching from Agilent corporate relations,after which some of us commenced a surprisingly long walk tothe life sciences manufacturing facility. Joined by the incrediblyknowledgeable Ching Soon-Tee (LC-MS engineering manager) atthe facility, we donned dust gowns and overshoes, then had topass a static electricity discharge test before proceeding to thefactory floor.

Agilent has more than 40 years of history in Singapore,dating from the time the company was part of Hewlett Packard.Agilent opened what it calls the automation solutions facility inthe country in 2009 to produce high-precision liquid-handlingand laboratory robotic instruments. They followed up with thelife sciences manufacturing facility in 2010.

The entire portfolio of Agilent’s LC-MS (as well as microarray)instrumentation is manufactured in the Singapore facility. Thisincludes the 6100 series single-quadrupole LC-MS, the 6200series accurate-mass time-of-flight LC-MS, the 6400 series triple-quadrupole LC-MS and the 6500 series accurate-mass quadrupoletime-of-flight LC-MS as well as the beast that is the 6560 newion mobility Q-TOF (quadrupole-time of flight) instrument.

According to Sui-Ching, the growing amount of public andprivate sector research and development in the country, coupledwith the availability of well-trained local workers and anexcellent supplier network (and possibly the favourable taxsystem), offers a pretty good environment for researchinstrumentation and scientific tools companies to develop andbuild high-end analytical instrumentation for the global market.Several other instrument manufacturers also have bases inSingapore.

For commercial reasons, I am not allowed to report too muchof what I saw. Agilent also weren’t too keen to tell me details

of the construction and specifications of individual componentssuch as the detectors or electron guns, or even how long it tookto put a machine together and what the annual factory outputis. I can tell you that the start of the process is to clean everypart thoroughly (and I mean very thoroughly) – just amicroscopic speck of dust or dirt in the wrong place can cause alot of problems. Cleaning is done with a selection of solventsand ovens.

Individual workers assemble each sub-unit according to verystrict and detailed work plans and these sub-units are puttogether later into the final instruments. These are testedextensively before being shipped out to the customer (seephoto).

The Agilent visit was a real highlight of my trip toSingapore. I got to see a side of modern analytical chemistrythat not many scientists experience and to learn a lot aboutinstrument manufacture and engineering. I was also quiteinterested to see that the Agilent factory uses fridges fromThermo Fisher.

In June last year, Agilent launched the latest addition to itsportfolio of LC/MS instruments – the 6495 LC/MS triple-quadrupole (QQQ) system (which I am doing my best to find thefunding for in my lab) – as well as their entry-level 6020 LC/MSsingle-quadrupole system, so the Singapore team should bemanufacturing instruments for a good while to come.

Dr Oliver Jones MRACI CChem is a senior lecturer in analytical chemistry at theAustralian Centre for Research on Separation Science (ACROSS) at RMIT Universityin Melbourne who is always happy to see behind the scenes. Oliver would also liketo thank the many people at Agilent who made this visit possible, including, butnot limited to, Tom Hennessy, Nicole Pendini, Sunil-Chidambar Kulkarni, DavinaLaw-Stewart, Caleb Ng, Robin Philp, Ching Soon-Tee, Saw Wan-Koon and Low Sui-Ching.


instrumentation

Mass spec behind the scenes

Agilent’s LC-MS Engineering Manager Ching Soon-Tee describes thetechnology of Agilent 6495 Curve Collision Cell and how each unit isassembled. The details on the part bins to the left of the picture givesome insight into the process of putting together the individualunits.

Low S

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economics

Ethane cracking is practised all over the world at scales from50 kt/year to over 2 Mt/year. How do the Australian economicscompare to those in the Middle East, South-East Asia and theUS?

In Australia, steam cracking to produce olefins is used forthe production of high-value plastics products (such as gas andwater piping). The stoichiometry is:

C2H6 → C2H4 + H2

The reaction is favoured by high temperatures (>800°C) andlow partial pressures, which are obtained by adding steam tothe system. The hot gases are rapidly quenched and thencompressed to help separate the products. A selectivehydrogenation process is used to remove small quantities ofacetylene also formed at high temperatures:

C2H2 + H2 → C2H4

The purified ethylene is separated and then polymerised by avariety of processes to produce polyethylene. This product isthen extruded to form the required commodity (e.g. pipes).

The Australian industry comprises two operations: one atBotany (300 kt/year), which uses ethane from the centralAustralian gas fields, and one at Altona (200 kt/year), whichuses ethane from Bass Strait, supplemented with LPG from localrefineries. These facilities are small compared with manyoperations in Asia, which unlike those in Australia have grownrapidly with the growth of China (see table below); for instancethe Singapore cracking capacity is more than five times that ofAustralia.

2013 Far East ethylene capacity and 10-year growth rate

Ethylene capacity Ethylene 10-year growth (t/year) (%)

Australia 502 000 –1.0

China 13 778 000 67.4

China Taiwan 4 006 000 41.0

India 3 315 000 27.6

Indonesia 600 000 8.3

Japan 6 935 000 1.3

Malaysia 1 723 000 3.7

Singapore 2 780 000 29.9

South Korea 5 630 000 12.6

Thailand 3 172 000 56.3

Total 42 441 000

A typical ethane cracking operation has inputs and outputsas shown in the next table.

The complex free radical nature of the pyrolysis leads toproducts higher in molecular weight than the ethane feedstock.For small-scale operations, these are usually used as furnacefuel. For large-scale operations, integrated into a petrochemicalcomplex, these materials are separated and result in by-productcredits.

Typical inputs and outputs for ethane cracking (wt/wt)INPUTS (wt/wt)Ethane 1.302

Ethane operating allowance (5.5%) 0.072

Furnace fuel 0.660

Fuel operating allowance (3%) 0.020

Total inputs 2.053

OUTPUTS (wt/wt)Ethylene 1.000

Propylene 0.034

Butadiene and other C4 olefins 0.034

Pyrolysis gasoline 0.022

Hydrogen 0.132

Methane 0.080

Total outputs 1.302

The impact of ethane price on the cost of ethyleneproduction is illustrated in the lower line of the graph for anethane cracker of 500 000 t/year ethylene capacity with acapital cost typical for a US Gulf construction of $850 million.

In many parts of the world (including parts of Australia), gasproduction cost is less than $2/GJ. Recovering the ethane costsan additional $1/GJ; so facilities that have access to such gasproduce ethylene for about $600/t; By comparison, tradedethylene prices are about $1300/t. This is the case in theMiddle East, which has attracted large-scale investments inpetrochemical plants to build on this feedstock cost advantageand, as a consequence of shale gas developments in the US, isnow driving a major resurgence of investment in the USchemical industry.

For Australia, ethane is traditionally priced on a scale relativeto the price of crude oil (typically $6–8/GJ). This is obviously amajor cost disadvantage relative to cracking operations in theMiddle East and US. Furthermore, because ethane can beincorporated into LNG, the cost of ethane could rise to match theexport LNG value, potentially more than $12/GJ.

For Australia, there is a further issue – the cost ofconstruction relative to other parts of the world. A commonview is that construction costs here are 50% higher than in theUS. This situation is reflected in the ‘HIGH CAPEX’ line in thegraph. This data shows that in order to produce ethylene in anew ethane cracker, the cost of ethane feedstock has to be wellbelow $9/GJ.

Australia is unique in the Pacific Rim of having imposed acarbon tax on emissions. For cracking operations, this resultsprincipally from emissions from the cracking furnace. With anemissions charge of $25/t of carbon dioxide, this adds about$55/t to the production cost. Applying such a tax withoutcommensurate application by regional players would furtherinhibit investment in Australia.

As far as the present operations are concerned, where plantsare older and have a significant portion of the capital written


Steam cracking: how do we stack up?

off, the production cost would give a positive productionmargin, but there is little likelihood of significant plantexpansions.

As this analysis shows, the main issue is the price offeedstock. Given the uncertainty in the eastern seaboard gasmarket with the potential for methane and ethane being pricedfor the expensive north-east Asia LNG trade, the obviousalternative is coal, the export price of which is in the region of$3–4/GJ and lower than $2/GJ for domestic use. Coal-basedroutes to olefins are now proven (in China 20 Mt/year of coal-based olefins facilities are planned) and offered by severalmajor technology suppliers. Since methanol is an intermediatein this route, it can also be applied to stranded gas reserves inthe remote regions of the country. However, such projects wouldalways be at the mercy of a pipeline to the nearest LNG facility.

Technology under development concerns the production ofethylene by catalytic cracking. Propylene is already produced inthis way by deep fluid-catalytic cracking (FCC), which is a

variant on a refinery FCC unit. The interest is to change thecatalyst composition to incorporate more ZSM-5 zeolite and usenaphtha as feedstock (rather than heavy fuel oil) to generatean olefin equilibrium in which ethylene is a significantcomponent. There is also interest in the direct catalyticcracking of heavy oils, including crude oil to ethylene. However,losses to coke are a significant problem.

Despite a long history, there are no commercially provendirect routes for the conversion of methane to ethylene.Oxidative coupling (OXCO process) is still the subject of muchresearch, the major issue being the selectivity of the process toethylene over the deep oxidation products carbon dioxide andwater. Recently, new proposals have revived interest in pyrolysisroutes to acetylene but coke lay-down is the major issue to beovercome.

Unfortunately, all of these alternatives (other than coal-based routes) require gas prices close to well-head productioncosts for viability.

New website, same great content

Access features, news and views from the latest issue and from our chemistry archives.

Visit our new online home at chemaust.raci.org.au

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P ro du ct io n co st s ($ /t )

Ethane price ($/GJ)

HIGH CAPEX

US GULF

iStockphoto/VIPDesignUSA

Sensitivity of ethylene production cost to ethane price.

For Australia, ethane is traditionallypriced on a scale relative to the priceof crude oil ... a major costdisadvantage relative to crackingoperations in the Middle East and US.

Duncan Seddon FRACI CChem is a consultant to coal, oil, gas andchemicals industries specialising in adding value to naturalresources.

education

Teaching is a vocation. Like parents, great teachers delight in thesuccess of their children and students. The creative process bringsmuch satisfaction and joy to the creator, whether it is the creationof a meal or the creation of an artistic masterpiece. Even thoughwe might complain about the tedium of household chores such asironing, there is also satisfaction in the creation of a well-ironedgarment from a mess of wrinkled fabric. Teachers help theirstudents create themselves (see October 2012 issue, p. 37). Brian Schiller, the recipient of the 2014 Prime Minister’s Prize forExcellence in Science Teaching in Primary Schools, said: ‘... mygreatest reward has always been in working with the childrenthemselves, witnessing them interacting in wonder with the worldaround them and fuelling their high level of creativity andimagination’.

The best-known national awards are the Prime Minister’s Prizesfor primary, secondary and tertiary education, the AustralianAwards for Teaching Excellence, the BHP Billiton Science andEngineering Teacher Awards, and the Australian Citations forOutstanding Contributions to Student Learning.

The RACI also has its state and national awards forcontributions to education. The RACI Centenary of Federation –Primary & Secondary Teaching Award is awarded by each stateBranch to recognise and reward outstanding excellence in theteaching of senior-secondary chemistry or the primary or junior-secondary science. For the purposes of these awards, the ACT isconsidered to be part of New South Wales and the NorthernTerritory to be part of South Australia. One national Primary andone national Secondary Teaching National Award can also bepresented to the most outstanding candidates from the Branches.Nominees and nominators for the RACI Centenary of Federation

Awards do not need to be RACI members.The Pearson RACI Chemistry Educator of the Year Award is for

junior Australian university academics teaching in the chemistrydiscipline.

The RACI Fensham Medal is the most senior award foreducation in the RACI, and recognises outstanding contributionsto the teaching of chemistry and science in general over anextended period. Nominees must have demonstrated outstandingachievement in chemistry and chemistry-related teaching andlearning excellence over a period of at least 10 years at theprimary, secondary or tertiary levels of chemical education, orthrough public or industry-based appointments.

The RACI Division of Chemical Education also has its ownawards. Up to three divisional citations can be awarded each yearin recognition of a significant contribution to chemical education.The divisional medal is awarded on the basis of the overallcontribution to chemical education in Australia in the previous10-year period, by way of research, teaching and/or promotion ofchemistry.

While the acknowledgement of personal achievements by asmall circle of family, friends and community was sufficient forRobert Bolt’s character, Sir Thomas More, most people needoccasional recognition of a job well done. This is important formorale. And especially so for teachers, who are often under-valued by the wider Australian society. Geoff McNamara, therecipient of the 2014 Prime Minister’s Prize for Excellence inScience Teaching in Secondary Schools, said: ‘It’s a recognitionthat what we are doing here in public education is importantand is valued’. Furthermore, awards often give persuasiveauthority to recipients and empower them to continue toimplement new ideas. Even more importantly, awards indicateto other teachers that it is OK for them to follow and thusspread good teaching and learning practices.

If you know outstanding chemistry or science educators,please encourage them to apply for an award. In particular,nomination for the RACI Centenary of Federation Awards onlyrequires a few pages. The deadline for all state and nationalawards is 30 June 2015 (www.raci.org.au/events-awards/education). Please contact the National Office,[email protected], for further information.

38 May 2015

Teaching awards acknowledge great teachers

Kieran F. Lim ( ) FRACI CChem([email protected]) is an associate professor in the Schoolof Life and Environmental Sciences at Deakin University.

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Sir Thomas More: Why not be a teacher? You’d be a fineteacher. Perhaps a great one.

Richard Rich: If I was, who would know it? You?Sir Thomas More: Your pupils, your friends, God. Not a bad

public, that ... And a quiet life.

Robert Bolt, A man for all seasons, 1960

This is the fourth article in the quartet on volatile sulfurcompounds (VSCs). I doubt if this quartet will stand the test oftime as do the string quartets of Joseph Hayden. This is themusic I listen to when writing, hoping that some of Hayden’screative genius may stimulate the brain cells. And four articleson VCSs in wine may seem a little too much, but it does reflectmy association with these compounds since my PhD days. Forreasons that I no longer remember, I was given the challenge ofmaking thiol complexes of rhodium. What I do remember,without any fondness, is the particular odour that seemed tofollow me after a day in the lab.

In my March column (p. 39), I mentioned that the lack ofreadily available nitrogen in grape juice was one factorcontributing to the production of H2S. Supplementation ofnitrogen by the addition of diammonium phosphate (DAP) iscommon practice, although it does come at a cost. A variety ofother yeast supplements are now available, which assist theyeast in its task of completing the fermentation. On the otherhand, if the amount of nitrogen in the grape can be enhancedthrough vineyard practices, the need for nitrogensupplementation may possibly be eliminated.

The total nitrogen content of the grape berry consists ofapproximately 60–65% proteins, 20% free amino acids and 15–18% peptides as well as a range of other nitrogenouscompounds. The main forms used by the yeast, the so-calledyeast-assimilable nitrogen, are free amino acids and theammonium ion, the latter being the basis for DAPsupplementation. Yeasts are rather fussy in regard to aminoacids. One yeast favourite is arginine and this is considered bysome oenologists as one of the most significant, if not the mostsignificant, contributor to yeast nutrition. Proline is often theamino acid of highest concentration in grapes, but is notutilised under typical anaerobic fermentation conditions.

Some years ago, Jessica Wade in her PhD project at CharlesSturt University examined the effect of irrigation and thetiming of nitrogen fertilisation on Shiraz grapes grown in theRiverina region. Jessica found that it was possible to vary theamino acid composition and especially the arginine to prolineratio, providing useful insights into how to use vineyardpractice to manage fruit composition. Geoff Johnston fromPirramimma in McLaren Vale has worked extensively on vineyardsoil management and has achieved his target of essentiallyeliminating the formation of H2S during fermentation. Geofftells me that he can see the difference between his fruit andthat from his growers in terms of the propensity for H2Sproduction. This is a good example of working grapes at theirsource, the vineyard, to get the desired outcome incomposition.

In red wine production, a small amount of oxygen never goesastray and this is one way to remove any H2S. One winemaker

once told me that he connects a garden hose to the base of thered wine fermenter and pumps air through it to minimise H2Sproduction. When pumping wine from a fermenter to an emptytank, a ‘spray ball’ can be used. This is like a showerheadthrough which the wine passes, collecting a small amount ofoxygen on the way. One winery where I worked used a woodensingle-piston pump to move wine around and this had theadded benefit of aerating the wine. Perhaps this is an earlyexample of the relatively modern technique of micro-oxygenation.

There are times when the above strategies do not work andthe H2S aroma remains. Copper fining (see March issue, p. 39)with copper(II) sulfate or citrate can be used to remove theoff-odour. Older winemaking practice may have used silver andeven cadmium salts! For reasons not yet known, the amount ofcopper(II) required is in considerable molar excess of the H2Sconcentration and the excess copper can lead to other qualitydefects such as the onset of oxidation and enhancedcolouration. A similar issue also exists with beer. Mark Smith ofthe Australian Wine Research Institute (AWRI) has drawn myattention to an electrochemical answer proposed by Thorne etal. (J. Inst. Brew. 1971, vol. 77, pp. 148–53). These authorsdemonstrated that placing copper electrodes in beer wouldallow copper(II) ions to be released in statu nascendi to reactwith the volatile sulfur compounds and thereby minimise theamount of copper(II) required. The approach was shown to beeffective on an industrial scale for beer production, but Icannot find any examples of its application in wine chemistry.

Increasingly, there are reports in the oenology literature thatthe H2S aroma returns over time in wines that have beenpreviously treated with copper(II). While I have oftensuggested that this may be due to the lower access to oxygenunder screw-cap seals, there would seem to be more to thechemistry than simply oxygen availability. There has long beenspeculation, particularly in the older French wine literature,that copper(I) is capable of reducing SO2 to H2S. This six-electron reduction of sulfur is something about which I havealways had considerable reservations. However, at the Crush2014 symposium in Adelaide, Marlize Viviers from the AWRIshowed that the combination of copper(II) and SO2 resulted inelevated concentrations of H2S, up to 40 times higher than theodour threshold in comparison to the control. The mechanismof the process still needs to be determined, and there must besome exciting chemistry occurring that hopefully might berevealed soon. So, perhaps this may not be the final article onVSCs. Maybe it is more of an unfinished symphony!

grapevine


From where does the H2S come?

Geoffrey R. Scollary FRACI CChem ([email protected])was the foundation professor of oenology at Charles SturtUniversity and foundation director of the National Wine andGrape Industry Centre. He continues his wine research at theUniversity of Melbourne and Charles Sturt University.

plants & soils

May 2015

Chemical communication among plants

Dr Deidre Tronson FRACI CChem used to be a mad scientist, but isnow the Good Little Banksia Lady who, in retirement, is anenthusiastic member of Scientists and Mathematicians in Schoolsat a local primary school. She has proudly raised three sciencegraduates. She has had separate careers in research and teaching,culminating in a position as part-time senior lecturer at theUniversity of Western Sydney, Hawkesbury campus.

Can we communicate with plants? Plant-growers from all overthe world think we can, if their ancient (deeply rooted?) storiesare true.

Reportedly, in China, the footsteps method of cultivation iswhere the gardener softly walks by his or her plants each day,encouraging them to be productive. From the other side of theworld, an elderly French gardener jokes that he bares hisbackside to the tomatoes, to show them what they should looklike when they are ripe. Across the Channel, we hear that someare convinced that talking to their plants encourages growth.Here in Australia, an expert on a radio gardening program wasasked: ‘Do the weeds know when you are on holiday? It seemsthey grow more when you are away!’

Perhaps, by observing the plants each day, these variousgardeners see potential problems early enough to fix them. Or perhaps there is really a way to communicate with plants.

Scientific research into chemical communication in plantshas a long history. Charles Darwin and his son were the first toshow that a chemical substance in the tips of plants wasaffected by light and ‘communicated’ this information to thegrowing seedling, causing it to grow towards the sun. Thiscompound was later called ‘auxin’ and is part of the gibberellingroup of plant hormones.

Makers of the US TV program MythBusters, knowing that‘data’ is not the plural of ‘anecdote’, devised a more rigoroustest to determine whether sound could encourage plants togrow. They played recordings of speech and different types ofmusic to equivalent plants in equivalent glasshouses, ensuringthat they included a negative control. They avoided placinghumans with the plants, in case the carbon dioxide from thebreath of a speaker affected the results. They concluded thatsound had a ‘plausible’ positive effect on plant growth(bit.ly/1C8LfAI).

Plants are indeed known to respond to mechanical stressessuch as touch and gravity. Vibrations or mechanical pressurecan cause changes in the shape of proteins embedded in plantmembranes, thus opening or closing various ion channels. This

can initiate electrical impulses, which in turn can startbiochemical cascades that change the metabolism of the plantin a way that turns genes on or off, causing the plant torespond appropriately. Examples of plants responding to touchare vines, trigger plants and shorter grass under the clothesline.Perhaps some plants are sensitive enough to the change inpressure caused by sound waves, and respond similarly(bit.ly/1MuHxD3).

But real communication is a two-way interaction, so doplants talk to us?

They certainly try. Using smell and colour, they attractanimals and insects to a food or shelter source – to benefit theplant, it must be admitted. They also use a chemical armoury torepel organisms that may eat them, or to attract beneficialorganisms to feed on these pests. When we detect an odour oncrushing or watering our plants, that is the plant telling us thatit is in danger. Very recent research has demonstrated thatplants can respond differently to attack by different insects(bit.ly/1xetatL).

Some compounds produced by a damaged plant actuallycommunicate with nearby plants, causing them to startproducing defensive chemicals of their own in a type of inducedimmune response. The jasmonates or their derivatives (e.g. methyl jasmonate) are commonly involved in theseinteractions. They have structural similarities to theprostaglandins (e.g. PG E2) which cause the inflammation thatis one of our own primary defences against invading organisms.

Another group of compounds important in plant defencesare the salicylates, which appear to ‘cross-talk’ to thejasmonates and often have an antagonistic relationship withthem. It is interesting to note that one of the effects of aspirinin our bodies is to reduce inflammation by opposing theproduction of prostaglandins.

Many other plant communication systems are slowly beingelucidated. Some plants initiate induced responses to attackusing compounds that are transported between their roots,using the hyphae of fungi as their transport mechanism. And Irecently heard a PhD student on the radio, wishing she couldask her seeds (chemically!) what signals they used betweenthem, so that they knew when to germinate. She is perseveringwith these attempts, hoping that her success will help makesome agricultural practices more efficient (ab.co/1AgOyQg).

So it seems that even respectable scientists doing rigorousresearch think that we can communicate with plants – if onlywe try hard enough – and use some chemistry.

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40

Driving along Victoria Street, Melbourne, for theumpteenth time, I looked up at the SkippingGirl sign with its glowing ‘neon’ tubes and forthe first time began to wonder about theindustrial chemistry behind the vinegar behindthe Skipping Girl.

The sign was commissioned by Nycander &Co as an advertisement for their Skipping Girlvinegar, and built by Neon Electric Signs in1936. The emergence of girls skipping in thesun signalled the end of winter in Sweden, fromwhence the Nycanders came, and a keenobserver would see some semblance of Swedishnational dress in ‘Little Audrey’s’ clothes.Nycanders went out of business in the mid-1960s, and when the building was demolishedin 1968 the sign was removed and after passing through severalhands, appears to have been lost. A new one was constructedand installed on the roof of an electroplater’s building a fewdoors from its original home, where fundraising by Friends ofAudrey and free electricity from AGL have enabled it to continueto grace the Abbotsford skyline.

Oskar Emil Nycander, born in about 1860, arrived inMelbourne from England in 1909. His company took over theold Shamrock Brewery in 1910 and began the manufacture ofyeast that was compressed into blocks and sold to bakers.Nycander was a bacteriologist who had studied in Copenhagenunder Emil Christian Hansen and worked in Denmark, Germanyand Derby (UK). He held a number of Danish, British andGerman patents concerning alcoholic fermentation and yeastproduction. The Melbourne Argus reported in August 1910 thata tour of the factory had been conducted for bakers, who werebeing encouraged to take up the new product in place of theirown individual yeast plants or supplies they got from brewerieswhere yeast was a by-product. Vinegar production commenced afew years later.

In April 1938, the Argus sponsored a Modern WorldExhibition in the Earl’s Court ballroom just across the river fromdowntown Melbourne. Nycanders displayed their Skipping Girlvinegar and provided descriptions of the manufacturing process,which started with malted barley in which diastase convertedstarch into sugars, and continued with fermentation by yeast toproduce an alcoholic solution much like beer. That liquid wassterilised and sprayed down a packed tower while air was blownup through the liquid as it trickled over the packing of beechtwigs and shavings into which a special bacterium had beeninoculated. The alcohol was thus converted to acetic acid butthe final product also contained aromatic esters and higheralcohols that derive from the original malt and give the vinegarits specific flavour.

With a touch of advertising genius, the company organised askipping contest for girls and held it on a stage adjacent to

their display stand. Heats for girls 11 yearsand under and 14 years and under wereskipped each afternoon, and the winnerscompeted in a final on Saturday 30th. Thejunior final was won by Lorna Rees and thesenior final by Sylvia Conroy of SouthMelbourne, who set a new endurance record byskipping continuously for 32 minutes 60 (sic)seconds.

When I was young, skipping was not justfor girls because it was part of the fitnessregime for boxers. I recall seeing aspiringpugilists working the rope at a gym just upthe street from where I lived. Skipping wasalso a competitive sport, in which groups likethe Amateur Skipping Association of Victoria

held annual championships, and some prominent peoplecompeted. One such was J.J. Brown, Victorian state secretary ofthe Australian Railway Union, who in 1948 established a newworld marathon skipping record – 21 138 turns in 110 minutes(192 turns a minute). The British skipping champion, Jim Allen,was amazed that someone could sustain three turns of the ropea second for nearly two hours, and wrote to the Argus askingthem to arrange a contest. As far as I can ascertain, nothingcame of it. Brown, described in the Australian Dictionary ofBiography as ‘a robust six-footer [183 cm], non-smoker,teetotaler and fitness fanatic’ skipped at the gymnasium of theVictorian Railways Institute, where in 1950 he improved on hisrecord by making 30 111 turns in 155 minutes (194 turns aminute or 3.2 a second).

Nycander died in 1927 (his wife in 1936), but the companysurvived them for many years. You can find on the internet aninteresting item by Neville A. Michie about his father, A.I. Michie, who worked for Nycanders from about 1928 to1954, starting as an assistant industrial chemist and eventuallybecame factory manager. When the company was purchased byMauri Brothers, he moved to Sydney and took charge of all theirvinegar and yeast factories in Australia. Accompanying the textis a photograph of Michie at work in the Nycander laboratory.

Mauri Brothers & Thompson were direct competitors ofNycanders. Originally an engineering firm that producedmachinery for the food industry, they had been manufacturingyeast in Melbourne since 1911 but in a decade of verticalintegration they took over some of their customers and in the1920s and 1930s they also began production of vinegar(Champions Vinegar). It was another wave of acquisitions in the1950s that resulted in the absorption of Nycanders, and theconglomerate was itself taken over by Burns, Philp in 1982.

letter from melbourne


Skipping Girl

Ian D. Rae FRACI CChem ([email protected]) is a veterancolumnist, having begun his Letters in 1984. When he is notcompiling columns, he writes on the history of chemistry andprovides advice on chemical hazards and pollution.


cryptic chemistry

Across9 Fuel sat around? Double negative. (7)10 Maintain and develop standard. (7)11 Deter cost explosion of electronic

equipment. (9)14 Let it change name. (5)16 Three element font. (5)18 Tie spiced curry to a plant protection

product. (9)22 Puncture parting. (7)24 Glycidol is one erythropoietin ex ID

mixup! (7)25 Reduced by use of iron? (9)28 Water second side. (5)30 Put away 1673161. (5)32 A mixture of zirconium, beryllium, lithium,

neon and uranium makes mist. (9)36 Ranges from canvas. (7)37 Earnings coming back. (7)

Down1 Consumed and recycled. (4)2 Sulfur ignited opening. (4)3 Friend holds a science unit. (6)4 Acetone’s functional group will not take

too much confinement. (4)5 Lift sound beams. (4)6 Sensed novel nitro group carries no

charge. (8)7 A 9 Across, perhaps, comes up in

Ultrafast Laser Spectroscopy. (4)

8 A very important stretch of DNA held upin culpable negligence suit. (4)

12 Hesitation about a lug. (3)13 Grain sounds ironic. (3)15 See 27 Down.16 A chromium document is strong and

sharp. (5)17 It represents chemists form four

elements. (1.1.1.1.1.)18 Iron media. (5)19 Sulfur produced water rush. (5)20 I dig up a compound containing a

carbon–nitrogen double bond. (5)21 A pulsed electron paramagnetic

resonance technique contained inprocedure seems appropriate. (5)

23 Hear tune about ethyl carbamate. (8)26 Electron at feed. (3)27 & 15 Down Holds the lashes for

batting. (6)28 9 Across reacts losing a fluorine and

accepting oxygen to make a substancethat dissolves. (6)

29 Electron, get on silver; get on. (3)30 Instrument venture. (4)31 To follow at 10−18. (4)32 House in fine structure. (4)33 Drill first – be on receiving end. (4)34 Scratch bottom. (4)35 Radical 32 Down lost nitrogen

balance. (4)

events

Graham Mulroney FRACI CChem is Emeritus Professor of Industry Education at RMIT University.Solution available online at Other resources.

ALTA 2015: Nickel-Cobalt-Copper, Uranium-REE andGold-Precious Metals Conference & Exhibition23–30 May 2015, Perth, WAwww.altamet.com.au/conferences/alta-2015

18th International Conference on OrganometallicChemistry Directed Towards Organic Synthesis(OMCOS-18)28 June – 2 July 2015, Barcelona, Spain www.omcos2015.com

11th International Symposium on Ionic Polymerization5–10 July 2015, Bordeaux, Francehttp://ip15.sciencesconf.org

35th Australasian Polymer Symposium13–15 July 2015, Gold Coast, Qldwww.35aps.org.au

12th International Conference on Materials Chemistry(MC12)20–23 July 2015, York, UKwww.rsc.org/events/international

24th International Symposium: Synthesis in OrganicChemistry20–23 July 2015, Cambridge, UKwww.rsc.org/events/international

IUPAC 201548th General Assembly 6–13 August 2015, 45th World Chemistry Congress 9–14 August 2015,Busan, Koreawww.iupac2015.org

13th Conference on Laser Ablation (COLA-2015)31 August – 4 September 2015, Cairns, Qld http://cola2015.org

13th Annual UNESCO/IUPAC Workshop andConference on Macromolecules and Materials7–10 September 2015, Port Elizabeth, South Africahttp://academic.sun.ac.za/unesco

22nd International Clean Air and EnvironmentConference 20–23 September 2015, Melbourne, Vic. http://casanz2015.com

4th Federation of Asian Polymer Societies –International Polymer Congress5–8 October 2015, Kuala Lumpur, Malyasia www.4faps-ipc.org.my

2015 Sustainable Industrial Processing Summit andExhibition9 October 2015, Turkeywww.flogen.org/sips2015

Pacifichem 201515–20 December 2015, Honolulu, Hawaiiwww.pacifichem.org

RACI events are shown in blue

Coming up• X-ray spectroscopy and the chemistry

of interfaces

• The remarkable lives of bees

• Can sharing your personal data protectyour freedom?

• Haber's rule and the influence ofexposure time on toxicity

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For more information on your bene�ts, please call RACI Member Advantageon 1300 853 352 or visit www.memberadvantage.com.au/raci

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April 3

2015 NATIONAL AWARDS

www.raci.org.au/awards

The RACI is a professional membershiporganisation and one of the mostimportant duties of the organisation isthe recognition and promotion of thecontributions and achievements of our members.

There are a range of prestigious awardscovering a broad range of areas fromschool education to applied researchthat are aimed at the full range ofmembers from Post Graduate Studentsto Distinguished Fellows.

These awards are open to all membersof the RACI who meet the specificaward requirements. Some can beapplied for while others requirenomination by third parties.

The awards are listed on the website atwww.raci.org.au/awards together withthe criteria requirements and proposedmethods. Any other information can berequested from [email protected] orby contacting the RACI National Officedirectly on (03) 9328 2033.

Presentation of the awards will be at aspecial dinner held in November 2015.

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faulty communication: the bottom line · 2018-02-27 · robyn taylor ph/fax (03) 9328 2033/2670...

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