aryl diazonium salts: new coupling agents in polymer and ... · 6 polymer grafting to aryl...
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Edited by
Mohamed Mehdi Chehimi
Aryl Diazonium Salts
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Aryl Diazonium Salts
New Coupling Agents in Polymer and Surface Science
Edited by Mohamed Mehdi Chehimi
The Editor
Dr. Mohamed Mehdi ChehimiUniversity Paris DiderotSorbonne Paris CitéITODYSUMR CNRS 708615 rue J-A de Baïf75013 ParisFrance
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Print ISBN: 978-3-527-32998-4ePDF ISBN: 978-3-527-65047-7ePub ISBN: 978-3-527-65046-0mobi ISBN: 978-3-527-65045-3oBook ISBN: 978-3-527-65044-6
Cover Design Adam-Design, WeinheimTypesetting Toppan Best-set Premedia Limited, Hong KongPrinting and Binding Markono Print Media Pte Ltd, Singapore
V
To Jean Pinson, with gratitude
VII
Contents
1 AttachmentofOrganicLayerstoMaterialsSurfacesbyReductionofDiazoniumSalts 1
JeanPinson1.1 A Brief Survey of the Chemistry and Electrochemistry
of Diazonium Salts 11.2 The Different Methods that Permit Grafting of Diazonium Salts 31.2.1 Electrochemistry 31.2.2 Reducing Substrate, Homolytic Dediazonation,
Reaction with the Substrate 41.2.3 Reducing Reagent 51.2.4 Neutral and Basic Media 61.2.5 Ultrasonication 61.2.6 Heating and Microwave 61.2.7 Mechanical Grafting 71.2.8 Photochemistry 71.3 The Different Substrates, Diazonium Salts, and Solvents
that Can Be Used 71.3.1 Substrates 71.3.2 Diazonium Salts 91.3.3 Solvents 101.4 Evidence for the Presence of a Bond between the Substrate
and the Organic Layer 111.4.1 Stability of the Layer 111.4.2 Spectroscopic Evidence for a Bond 121.5 From Monolayers to Multilayers 131.5.1 Monolayers 141.5.2 Layers of Medium Thickness 161.5.2.1 Thick Layers 191.6 Structure and Formation of Multilayers 21
Preface XV ListofContributors XVII
VIII Contents
1.6.1 Chemical Structure 211.6.2 The Spatial Structure of the Layers 221.6.3 Compactness of the Layers 231.6.4 Swelling of the Layer 241.6.5 Electron Transfer through the Layers 241.6.6 The Formation Mechanism of Multilayers 251.7 Conclusion 27 References 27
2 Aryl–SurfaceBonding:ADensityFunctionalTheory(DFT)SimulationApproach 37
NanShao,ShengDai,andDe-enJiang2.1 Introduction 372.2 Density Functional Theory 382.3 Bonding between Aryl and Various Substrates 382.3.1 On Graphite/Graphene 392.3.1.1 On the Basal Plane 392.3.1.2 On the Edges of Graphene 422.3.2 On Carbon Nanotubes 442.3.3 On Metal Surfaces 452.4 Summary and Outlook 48 Acknowledgments 49 References 50
3 PatternedMolecularLayersonSurfaces 53 AlisonJ.Downard,AndrewJ.Gross,andBradleyM.Simons3.1 Methods Based on Scanning Probe Lithography 533.1.1 AFM 543.1.2 SECM 543.1.3 Spotting 563.2 Methods Based on Soft Lithography 573.2.1 Printing 573.2.2 Molds 593.2.3 Nanosphere Lithography 593.3 Methods Based on Lithography 603.4 Methods Based on Surface-Directed Patterning 623.4.1 Modification of Si Surfaces 633.4.2 Modified Electrode Arrays 643.5 Summary and Conclusions 66 References 68
4 AnalyticalMethodsfortheCharacterizationofArylLayers 71 KarstenHinrichs,KatyRoodenko,JörgRappich,
MohamedM.Chehimi,andJeanPinson4.1 Introduction 714.2 Scanning Probe Microscopies 71
Contents IX
4.3 UV–VIS Spectroscopy: Transmission, Reflection, and Ellipsometry 72
4.4 IR Spectroscopy 724.4.1 Transmission Spectroscopy 734.4.2 Reflection Spectroscopy 744.4.3 Infrared Spectroscopic Ellipsometry (IRSE) 754.4.4 IRSE Surface Characterization 774.4.5 InSitu IR Spectroscopy: ATR and IRSE 794.5 Raman Spectroscopy and Surface-Enhanced Raman
Scattering (SERS) 834.6 X-ray Photoelectron Spectroscopy (XPS) 844.7 X-ray Standing Waves (XSW) 914.8 Rutherford Backscattering 934.9 Time of Flight Secondary Ion Mass Spectroscopy 934.10 Electrochemistry 944.11 Contact Angle Measurements 964.12 Conclusion 96 References 98
5 ModificationofNano-objectsbyArylDiazoniumSalts 103
Dao-JunGuoandFakhradinMirkhalaf5.1 Introduction 1035.2 Electrochemical Modification of Nano-objects
by Reduction of Diazonium Salts 1055.2.1 Surface Modification of Carbon Nano-objects via Electrochemical
Reduction of Aryl Diazonium Cations 1055.2.2 Surface Modification of Metal and Metal Oxide Nano-objects via
Electrochemical Reduction of Aryl Diazonium Cations 1115.3 Chemical Modification of Nano-objects by Reduction
of Diazonium Salts 1125.3.1 Surface Modification of Carbon Nano-objects via Chemical Reduction
of Aryl Diazonium Cations 1125.3.2 Surface Modification of Metal and Metal Oxide Nano-objects via
Chemical Reduction of Aryl Diazonium Cations 1165.4 Summary and Conclusions 119 Acknowledgments 120 References 120
6 PolymerGraftingtoArylDiazonium-ModifiedMaterials:MethodsandApplications 125
SarraGam-Derouich,SamiaMahouche-Chergui,HatemBenRomdhane,andMohamedM.Chehimi
6.1 Introduction 1256.2 Methods for Grafting Coupling Agents from Aryl Diazonium
Compounds 127
X Contents
6.3 Grafting Macromolecules to Surfaces through Aryl Layers 1306.3.1 Binding Macromolecules to Surfaces by a Grafting
from Strategy 1306.3.1.1 Surface-Initiated Atom Transfer Radical Polymerization
(SI-ATRP) 1306.3.1.2 Surface-Initiated Reversible Addition–Fragmentation
Chain Transfer (SI-RAFT) 1426.3.1.3 Surface-Initiated Photopolymerization 1436.3.1.4 Alternative Methods 1466.3.2 Attachment of Macromolecules through Grafting
onto Strategies 1476.3.2.1 Photochemical Attachment 1476.3.2.2 Ring Opening 1486.3.2.3 Acylation 1496.3.2.4 Click Chemistry 1496.3.2.5 Diazotation of Substrates and Macromolecules 1506.4 Adhesion of Polymers to Surfaces through Aryl Layers 1516.5 Conclusion 153 References 153
7 GraftingPolymerFilmsontoMaterialSurfaces:TheOne-StepRedoxProcesses 159
GuyDeniau,SergePalacin,AliceMesnage,andLorraineTessier7.1 Cathodic Electrografting (CE) in an Organic Medium 1607.1.1 Direct Cathodic Electrografting of Vinylic Polymers 1607.1.2 Indirect Cathodic Electrografting 1627.2 Surface Electroinitiated Emulsion Polymerization (SEEP) 1647.2.1 Characterization of Poly(Butyl Methacrylate) Films 1667.2.2 Determination of the Film Structure 1677.2.3 Reduction of Protons and the Role of Hydrogen Radicals 1697.2.4 Mechanism of SEEP 1707.3 Chemical Grafting via Chemical Redox Activation (Graftfast™) 1717.3.1 Process without Vinylic Monomer 1727.3.2 Process with Vinylic Monomer 1747.3.2.1 Type of Materials 1747.3.2.2 Parameters Controlled in the Process 1747.4 Summary and Conclusions 177 References 178
8 ElectrograftingofConductiveOligomersandPolymers 181
JeanChristopheLacroix,JalalGhilane,LuisSantos,GaelleTrippe-Allard,PascalMartin,andHyacintheRandriamahazaka
8.1 Introduction 1818.2 Conjugated Oligomers and Polymers 181
Contents XI
8.3 Surface Grafting Based on Electroreduction of Diazonium Salts 184
8.4 Polyphenylene and Oligophenylene-Tethered Surface Prepared by the Diazonium Reduction of Aniline or 4-Substituted Aniline 187
8.5 n-Doping and Conductance Switching of Grafted Biphenyl, Terphenyl, Nitro-biphenyl and 4-Nitroazobenzene Mono- and Multilayers 187
8.6 p-Doping and Conductance Switching of Grafted Oligo-Phenylthiophene or Oligothiophene Mono- and Multilayers 190
8.7 p-Doping and Conductance Switching of Grafted Oligoaniline Mono- and Multilayers 192
8.8 Conclusion and Outlook 193 References 195
9 TheUseofArylDiazoniumSaltsintheFabricationofBiosensorsandChemicalSensors 197
J.JustinGooding,GuozhenLiu,andAliciaL.Gui9.1 Introduction 1979.1.1 Sensors and Interfacial Design 1979.1.2 Molecular Level Control over the Fabrication
of Sensing Interfaces 1989.2 The Important Features of Aryl Diazonium Salts
with Regard to Sensing 2009.3 Sensors and Biosensors Fabricated Using Aryl
Diazonium Salts 2019.3.1 Chemical Sensors – Sensors Fabricated via the Immobilization
of Chemical Recognition Species 2019.3.2 Biosensors 2059.3.2.1 Enzyme Biosensors 2069.3.2.2 Immunobiosensors 2089.3.2.3 DNA-Based Biosensors 2109.3.2.4 Cell-Based Biosensors 2139.4 Conclusions 213 References 214
10 DiazoniumCompoundsinMolecularElectronics 219 RichardMcCreeryandAdamJohanBergren10.1 Introduction 21910.2 Fabrication of Molecular Junctions Using Diazonium Reagents 22210.2.1 Substrates for Diazonium-Derived Molecular Junctions 22210.2.2 Surface Modification Using Diazonium Chemistry 22310.2.3 Application of Top Contacts 22510.3 Electronic Performance of Diazonium-Derived
Molecular Junctions 22610.3.1 Surface Diffusion Mediated Deposition (SDMD) 22710.3.2 Structural Control of Molecular Junction Behavior 230
XII Contents
10.3.3 Redox Reactions in Molecular Junctions 23210.3.4 Microfabricated Molecular Devices Made
with Diazonium Chemistry 23310.4 Summary and Outlook 235 Acknowledgments 236 References 236
11 ElectronicPropertiesofSiSurfacesModifiedbyArylDiazoniumCompounds 241
JörgRappich,XinZhang,andKarstenHinrichs11.1 Introduction 24111.2 Experimental Techniques to Characterize Electronic Properties
of Si Surfaces in Solutions 24211.2.1 InSitu Photoluminescence and Photo Voltage Measurements 24211.2.2 InSitu PL and PV Measurements during
Electrochemical Grafting 24411.2.3 Reaction Scheme of the Electrochemical Grafting via
Diazonium Ions 24511.2.4 Change in IPL and UPV during Electrochemical Grafting
onto Si Surfaces 24611.2.5 Change in Band Bending and Work Function after
Electrochemical Grafting onto Si Surfaces 24811.2.6 pH Dependence and Enhanced Surface Passivation 24911.3 Conclusion and Outlook 251 Acknowledgments 252 References 252
12 Non-DiazoniumOrganicandOrganometallicCouplingAgentsforSurfaceModification 255
FetahI.Podvorica12.1 Amines 25512.1.1 Characterization of the Grafted Layer 25712.1.1.1 Electrochemical Methods 25712.1.1.2 Surface Analysis Techniques 25812.1.2 Chemical Grafting 25912.1.3 Localized Electrografting 26012.1.4 Grafting Mechanism 26112.1.5 Applications 26212.2 Arylhydrazines 26412.3 Aryltriazenes 26612.4 Alcohols 26712.4.1 Observation and Characterization of the Film 26812.4.2 Applications 26912.5 Grignard Reagents 27012.5.1 Characterization of the Layers 27112.5.2 Grafting Mechanism 272
Contents XIII
12.6 Onium Salts 27212.6.1 Iodonium Salts 27212.6.2 Sulfonium Salts 27312.6.3 Ammonium Salts 27312.7 Alkyl Halides 27412.8 Conclusion 275 References 276
13 VariousElectrochemicalStrategiesforGraftingElectronicFunctionalMoleculestoSilicon 283
DineshK.Aswal,ShankarPrasadKoiry,andShivKumarGupta13.1 Introduction 28313.2 Architecture of Hybrid Devices 28413.2.1 Molecular Dielectrics and Wires 28513.2.2 Molecular Diodes 28613.2.3 Resonant Tunnel Diodes 28613.2.4 Molecular Transistors 28613.3 Electrografting of Monolayers to Si 28713.3.1 Essential Requirements 28713.3.2 Experimental Process of Electrografting 28713.4 Negative Differential Resistance Effect in a Monolayer
Electrografted Using a Diazonium Complex 28813.4.1 Electrografting of DHTT 28813.4.2 NDR Effect in DHTT Monolayers 29013.5 Dielectric Monolayers Electrografted Using Silanes 29313.5.1 Mechanism of Electrografting 29313.5.2 Electrical Characterization 29413.6 Molecular Diodes Based on C60/Porphyrin-Derivative Bilayers 29513.6.1 Fabrication Process 29613.6.1.1 Electrografting of Acceptor C60 Layer on Si 29613.6.1.2 Self-Assembly of Donor Porphyrin Derivative Layer on C60/Si 29713.6.2 Rectification Characteristics of D–A Bilayers 29813.7 Memory Effect in TPP-C11 Monolayers Electrografted
Using a C=C Linker 30113.7.1 Electrografting of TPP-C11 Monolayer 30113.7.2 Electrical Bistability and Memory Effect 30313.8 Summary 305 References 305
14 PatentsandIndustrialApplicationsofArylDiazoniumSaltsandOtherCouplingAgents 309
JamesA.Belmont,ChristopheBureau,MohamedM.Chehimi,SarraGam-Derouich,andJeanPinson
14.1 Introduction 30914.2 Patents 30914.2.1 The Surface Chemistry of Diazonium Salts 309