exploration of aurone system in mercury sensing
TRANSCRIPT
RESEARCH POSTER PRESENTATION DESIGN © 2019
www.PosterPresentations.com
Middle Tennessee State University, Department of ChemistryKoda Hengstenberg & Dr. Scott Handy
Exploration of Aurone System in Mercury Sensing
Why Detect Mercury?
How Does Fluorescence Work?
General Oxymercuration Reaction
N
OH O
O
Hg2+
N
O
O
O
HgCl
MS7, A reported Hg2+ fluorescent probe designed by Yang, B. et Al.
Environment:- Mercury is a type of toxic metal that comes in various
forms in the environment.
- Amount of mercury in the environment has skyrocketedsince since industrialization
- Estimated ~70,000 tons of mercury in the oceans alone!
Effects:- High doses cause Minamata Disease
- Exposure can harm the brain, heart, kidneys, lungs, and immune system
- Causes nervous system development issues in utero
- Loss of neurons with reactive proliferation of glial cells
- Leads to vascular congestion, petechialhemmorhage, and edema
- Fluorescence occurs when a compound is irradiated with some frequency of energy (λ). Once excited, the relaxtion of the molecule emits another wavelength. This emission is the
molecule's fluorescence
Mercury Sensor Synthesis
Conclusion
Future
References Acknowledgments I would like to thank the Undergrad Research Experience and Creative Activity at Middle Tennessee State University for
funding this research.. Special thanks to Dr. Scott Handy for his guidance and mentorship throughout this project
Department of Chemistry
UV
Abso
rban
ce
0
0.2
0.4
0.6
0.8
λ (nm)
320 340 360 380 400 420 440 460 480 500 520 540 560 580 600 620 640 660 680 700 720
UV
Abso
rban
ce
0
0.2
0.4
0.6
0.8
λ (nm)320 340 360 380 400 420 440 460 480 500 520 540 560 580 600 620 640 660 680 700 720
Flourescence
Emiss
ion
0
100
200
300
400
λ (nm)500 511 522 533 544 555 566 577 588 599 610 621 632 643 654 665 676 687 698
Flourescence
Emiss
ion
0
125
250
375
500
λ (nm)500 511 522 533 544 555 566 577 588 599 610 621 632 643 654 665 676 687 698
O
O
OH
O
O
O Hg
4-Hydroxyallylaurone Mercury 4-Hydroxyallyaurone
O
OH
Br
K2CO3
O
O
O
O
O
O
OO
O
HOGuanidine/HCl;Urea ~ 190oC
O
O O
O
O
O
O
Guanidine/HCl;Urea
~ 190oC
Br
K2CO3
Highest Yield?
O
O
HgCl2
OHg
O
O
O
O
Guanidine/HCl;Urea
O
O
O
~ 190oCO
O
OH
HO
O
Br
K2CO3
O
O
BrK2CO3
OH
O
O
O
~ 190oC
Guanidine/HCl;Urea
Highest Yielding Synthesis Alternate Pathway
Optimization:- A shift in fluorescence - Intramolecular H-bond- Hypothesized greater drecrease in flourescence intensity- Potential for solvent solubility manipulation
Reaction Properties:- Intramolecular- Speedy reaction time- Terminal alkene selectivity- Fluorescent "OFF-Switch"
Possible Issues:- Interaction with other cations (e.g. Ca2+, Zn2+, Ag2+)- Insignificant drop in fluorescence intensity
Eto, Komyo, et al. “Differential Diagnosis between Organic and Inorganic Mercury Poisoning in Human Cases-The Pathologic Point of View - Komyo Eto, Yukio Takizawa, Hirokatsu Akagi, Koichi Haraguchi, Shigeyuki Asano, Naohiko Takahata, Hidehiro Tokunaga, 1999.” SAGE Journals, 1 Jan. 1993.
Lai, Qi, et al. “Rational Design and Synthesis of Yellow-Light Emitting Triazole Fluorophores with AIE and Mechanochromic Properties.” Chemical Communications, The Royal Society of Chemistry, 7 Mar. 2019.
Fulghum, Lisa. “Ca2+ Detection in Muscle Tissue Using Fluorescence Spectroscopy.” World Precision Instruments, World Precision Instruments, 3 May 2018.