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Design and Synthesis of Novel Fluorescence Constructs for The DESIGN AND SYNTHESIS OF NOVEL FLUORESCENCE CONSTRUCTS FOR THE DETECTION OF ENVIRONMENTAL ARSENIC by VIVIAN CHIBUZO EZEH (Under the Direction of TODD C. HARROP) ABSTRACT Arsenic compounds are classified as group 1 carcinogens and the maximum contamination level in drinking water is set at 10 ppb by the United States Environmental Protection Agency. Methods currently approved for monitoring environmental arsenic are classified as colorimetric and instrumental methods. However, toxic byproducts (arsine gas and mercury) are formed in colorimetric methods, while instrumental methods require high maintenance costs. Therefore developing a sensitive, safe, and less expensive detection technique for arsenic is needed. One strategy involves the development of new imaging tools using small molecule fluorescent sensors, which will offer a sensitive and inexpensive method of arsenic detection in environmental samples. Emphasis will be on As(III) compounds because they are prevalent in the environment. To accomplish this goal, the coordination chemistry of As(III) was studied to discover new As(III) chemistry/preference for thiols. One finding from this work is the As(III)-promoted redox rearrangement of a benzothiazoline-containing compound to afford a four-coordinate As(III) complex and the benzothiazole analog. The knowledge gained was used to design two fluorescent chemodosimeters for As(III). The first generation sensors, named ArsenoFluors (AFs), were designed to contain a benzothiazoline functional group appended to a coumarin fluorescent reporter and were prepared in high yield by multi-step organic synthesis. The sensors react with As(III) to afford a highly fluorescent coumarin-6 dye (benzothiazole analog), which results in a 20 – 25 fold increase in fluorescence intensity and 0.14 – 0.23 ppb detection limit for As(III) in THF at 298 K. In addition, the reaction is complete within 30 min and is selective for As(III) over other toxic ions such as Hg(II) and Pb(II). The sensors also react with a common environmental species of As(III), namely sodium arsenite, in a THF/CHES (1:1, pH 9) buffer mixture. However, the reaction is slower (time > 5 h) and the enhancement of fluorescence is modest (1.5- to 3- fold) due to the quenching of the coumarin dye in a high polarity solvent. Finally, the mechanism for the As(III)-promoted formation of the fluorescent benzothiazole compounds from the benzothiazolines is proposed. INDEX WORDS: Arsenic, Fluorescence Detection, Environment, Sulfur DESIGN AND SYNTHESIS OF NOVEL FLUORESCENCE CONSTRUCTS FOR THE DETECTION OF ENVIRONMENTAL ARSENIC by VIVIAN CHIBUZO EZEH B.Sc, University of Ibadan, Nigeria, 2006 A Dissertation Submitted to the Graduate Faculty of The University of Georgia in Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSOPHY ATHENS, GEORGIA 2013 © 2013 VIVIAN CHIBUZO EZEH All Rights Reserved DESIGN AND SYNTHESIS OF NOVEL FLUORESCENCE CONSTRUCTS FOR THE DETECTION OF ENVIRONMENTAL ARSENIC by VIVIAN CHIBUZO EZEH Major Professor: Todd C. Harrop Committee: Michael K. Johnson Jason Locklin Electronic Version Approved: Maureen Grasso Dean of the Graduate School The University of Georgia August 2013 DEDICATION I dedicate this work to Prof. Kehinde Okonjo, for motivating me to pursue a career in Chemistry. iv ACKNOWLEDGEMENTS I owe the successful completion of my graduate studies to the role of several people that have assisted me along the way. I appreciate Prof. Todd Harrop for the opportunity to work in his research group and for being an amazing teacher and mentor. Members of my advisory committee, Prof. Michael Johnson and Prof. Jason Locklin, provided useful feedback that helped me improve on my research, writing and presentation skills. Thank you. Former and present members of the Harrop’s research group; Dr. Ashis Patra, Dr. Eric Gale, Wren Cheatum, Koustubh Dube, Brian Sanders, Melody Rhine, Phan Truong, Ellen Broering, Ramsey Steiner and Emily Betchy, thank you for creating a collegial work environment where I could thrive in my studies. Furthermore, I thank the Chemistry Department at the University of Georgia for an excellent education and the faculty and staff for support and assistance during my studies. I thank my parents; Mr. and Mrs. Ezeh, my brothers; Chinedu and Chike, and extended family for their support. Also, my friends: Barr. Funmi Alonge, Dr. Bo Zhang, Dr. Simon Owino, etc. for providing companionship and assistance during my graduate studies program. Finally, financial support for my research was provided by the University of Georgia Research Foundation and National Research Foundation. Dissertation year support was provided by Kenyon College, where I was provided the space to write my dissertation. Thank you. v TABLE OF CONTENTS Page ACKNOWLEDGEMENTS .............................................................................................................v LIST OF TABLES ....................................................................................................................... viii LIST OF FIGURES ....................................................................................................................... ix CHAPTER 1 INTRODUCTION AND LITERATURE REVIEW .....................................................1 General Introduction to Arsenic...............................................................................1 Arsenic in the Environment ...................................................................................10 Toxicity of Arsenic Compounds ............................................................................16 Coordination Chemistry of As(III) ........................................................................19 Regulation and Detection of Arsenic Compounds.................................................23 Introduction to Fluorescence Spectroscopy ...........................................................29 Intent of Research ..................................................................................................33 2 SYNTHESIS AND CHARACTERIZATION OF S-BASED LIGANDS FOR RECEPTOR DESIGN IN As(III) SENSORS..............................................................36 Abstract ..................................................................................................................36 Introduction ............................................................................................................37 Results and Discussion ..........................................................................................38 Conclusion .............................................................................................................56 Experimental Section .............................................................................................56 vi 3 ARSENOFLUORS (AFs): DESIGN, SYNTHESIS AND PROPERTIES OF FLUORESCENT CHEMODOSIMETERS FOR As(III) UTILIZING BENZOTHIAZOLINE TO BENZOTHIAZOLE CONVERSIONS. ..........................84 Abstract ..................................................................................................................84 Introduction ............................................................................................................84 Results and Discussion ..........................................................................................86 Conclusion ...........................................................................................................108 Experimental Section ...........................................................................................109 4 CONCLUSIONS AND FUTURE DIRECTIONS……….........................................134 Conclusions ..........................................................................................................134 Future Directions .................................................................................................135 REFERENCES………. ...............................................................................................................138 APPENDICES………. ................................................................................................................159 A DESIGN, SYNTHESIS AND PROPERTIES OF DANSYL-APPENDED CHEMOSENSORS FOR As(III) FLUORESCENCE DETECTION…………………..…......159 vii LIST OF TABLES Page Table 1: Size properties of arsenic (Å) ............................................................................................3 Table 2: Experimentally determined As – Element bond energies in the gas phase (kJ/mol) .........4 Table 3: Arsenic content in the soils of various countries .............................................................15 Table 4: Overall Stability Constants of As(III)-thiolate Complexes Obtained from Best Fits of Near-UV Spectral Titration................................................................................................17 Table 5: Summary of crystal data and intensity collection and structure refinement parameters for L3·HCl , L2 and [As( L5)I]...........................................................................................81 Table 6: Selected bond distances (Å) and bond angles (deg) for L3·HCl ....................................82 Table 7: Selected bond distances (Å) and bond angles (deg) for [As( L5)I] ..................................82 Table 8: Selected bond distances (Å) and bond angles (deg) for L2 .............................................83 Table 9: Summary of crystal data and intensity collection and structure refinement parameters for AF1 .............................................................................................................................132
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