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PERFLUOROALKYL (ARYL) SULFONIMIDE ZWITTERIONS Hua Mei Clemson University, [email protected]

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PERFLUOROALKYL (ARYL) SULFONIMIDE ZWITTERIONS Hua Mei Clemson University, Hmei@Clemson.Edu Clemson University TigerPrints All Dissertations Dissertations 12-2006 PERFLUOROALKYL (ARYL) SULFONIMIDE ZWITTERIONS Hua Mei Clemson University, [email protected] Follow this and additional works at: https://tigerprints.clemson.edu/all_dissertations Part of the Organic Chemistry Commons Recommended Citation Mei, Hua, "PERFLUOROALKYL (ARYL) SULFONIMIDE ZWITTERIONS" (2006). All Dissertations. 40. https://tigerprints.clemson.edu/all_dissertations/40 This Dissertation is brought to you for free and open access by the Dissertations at TigerPrints. It has been accepted for inclusion in All Dissertations by an authorized administrator of TigerPrints. For more information, please contact [email protected]. PERFLUOROALKYL (ARYL) SULFONIMIDE ZWITTERIONS ——————————————— A Dissertation Presented to the Graduate School of Clemson University _____________________________ In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy Organic Chemistry ______________________________ by Hua Mei December 2006 ______________________________ Accepted by: Dr. Darryl D. DesMarteau, Committee Chair Dr. Dev P. Arya Dr. Stephen Creager Dr. Dennis W. Smith, Jr. ABSTRACT This research focuses on superacid perfluoroalkyl(aryl) sulfonimides and their derivatives as a source of stable zwitterionic salts. The strong resonance stabilization of sulfonimides imparts unexpected stability to the zwitterions. Two types of zwitterions were investigated. The first are symmetrical diaryliodonium zwitterions (DZs) as potential photo acid generators (PAGs) for microlithography. Driven by the demand for smaller feature sizes in the microelectronics industry, microlithography using shorter wavelength light has evolved and new PAGs are of interest. New DZs are potentially useful because they have good thermal stability and may be structurally modified to alter their spectral absorption characteristics. As an extension of earlier research in our group, three new symmetric difunctional DZs (p- + - PhI PhSO2N SO2Rf)2 (Rf = C4F8, or C6F12, or C2F4OC2F4) were synthesized. Similar to earlier monofunctional DZs, they have very good thermal stability and high extinction coefficients. The second zwitterions were developed for electrochemical applications. In order to incorporate strong acid electrolytes into nanoporous carbon electrodes for Polymer Electrolyte Membrane (PEM) fuel cells, we have synthesized functional diazonium zwitterions (FDZs) based on fluorinated sulfonimides. FDZs provide a means to covalently attach the electrolyte to the carbon substrate as an alternative to physical deposition of an electrolyte from a solution. The typical electrolyte deposition for membrane electrode assembly using solubilized Nafion® cannot be used for nanoporous iii carbons due to size exclusion. Most diazonium salts are unstable at room temperature and some are explosive. Three series of thermally stable FDZs were successively prepared. + - Monofunctional Diazonium Zwitterions (MFDZs) p-N2 PhSO2N SO2Rf (Rf = CF3 or C4F9) were the first example and were shown to have surprisingly high decomposition temperatures and good solubility in organic solvents. Then, Difunctional Diazonium + - Zwitterions (DFDZs) (p-N2 PhSO2N SO2Rf)2 (Rf =C4F8 or C6F12) were synthesized from the experience of making DZs and MDZs. These salts only dissolve in more polar solvents such as DMSO and exhibited good thermal stability. Finally, Multifunctional + - Diazonium Zwitterions (MFDZs) p-N2 PhSO2N SO2RfSO2N(H)SO2CF3 (Rf = C4F8 or C6F12) were prepared with two acidic proton positions on grafting. These salts had good solubility in water and several organic solvents. In principle, all of these salts are composed of acidic protons upon grafting to carbon. The best carbon coating method is still under investigation. An alternative route to higher ion exchange capacity after attachment to carbon was envisaged via two other types of FDZs. A trifluorvinyl ether (TFVE) of the type p- + - N2 PhSO2N SO2PhOCF=CF2 was prepared and can in principle be used to prepare a multifunctional polymer using step-growth polymerization with an appropriate functional + - TFVE monomer. Similarly, the novel FDZs p-N2 PhSO2N SO2RfSO2N(H)SO2F (Rf = C4F8 or C6F12) can be used to grow or attach a polymer by condensation reaction with an appropriate amide. DEDICATION I dedicate this work to my Dad and my Mom. This dissertation exists because of their love and support. ACKNOWLEDGMENTS All of my work could not have been completed without the support of several special people. I am especially grateful to my advisor, Dr. Darryl. D. DesMarteau, whose advice, not only in research but also in personal development, has immeasurably contributed to my growth as a chemist and as a person. His incredible scientific capability and vast amount of knowledge have been an inspiration through my pursuit of this PHD degree. I would also like to thank Dr. Stephen Creager for valuable creative discussions and advice on the fuel cell project. And gratitude goes to my committee members Dr. Dennis W. Smith, Jr. and Dr. Dev P. Arya for providing their beneficial insights regarding my research work. Special recognition goes to Dr. VanDerveer Don for helping me with X-ray structures of my compounds. Group members, Dr. Jie Zhang, Dr. Shuang Zhou, Dr. Monika Mujkic and Tom Hickeman, have enriched my work and life with their help in the laboratory, and simply with their encouragement, support, and friendship. I dedicate this thesis to my parents, my mom Liming Cui and my dad Xiaolin Mei who passed away in March 2006, who provide me with the example of personal sacrifice that helps me believe anything is possible. TABLE OF CONTENTS Page TITLE PAGE......................................................................................................................... i ABSTRACT........................................................................................................................... ii DEDICATION....................................................................................................................... iv ACKNOWLEDGEMENTS................................................................................................ v LIST OF TABLES................................................................................................................ viii LIST OF FIGURES.............................................................................................................. viiii LIST OF SCHEMES............................................................................................................ x CHAPTER 1. INTRODUCTION ............................................................................................... 1 1.1 Preface ...................................................................................................... 1 1.2 Zwitterions............................................................................................... 1 1.3 Super Acid Bis((perfulroalkyl)sulfonyl)imdes and Their Derivatives .................................................................................. 2 1.4 Diaryliodonium Salts in Photo Acid Generators (PAGs)............................................................................................................ 6 1.5 PEM Fuel Cell......................................................................................... 12 1.6 General Experimental Methods........................................................... 17 2. IODONIUM ZWITTERIONS .......................................................................... 22 2.1 Introduction ............................................................................................. 22 2.2 Research and Discussion ...................................................................... 28 2.3 Experimental ........................................................................................... 32 2.4 Conclusion ............................................................................................... 39 3. FUNCTIONAL DIAZONIUM ZWITTERIONS ......................................... 40 3.1 Introduction ............................................................................................. 40 3.2 Research and Discussion ...................................................................... 52 vii Table of Contents (Continued) Page 3.3 Experimental ........................................................................................... 64 3.4 Conclusion ............................................................................................... 80 4. PERFLUOROALKYL (ARYL) SULFONIMIDE DIAZONIUM ZWITTERIONS MONOMERS ............................................ 81 4.1 Introduction ............................................................................................. 81 4.2 Research and Discussion ...................................................................... 87 4.3 Experimental ........................................................................................... 93 4.4 Conclusion ............................................................................................... 104 APPENDICES....................................................................................................................... 105 LITERATURE CITED........................................................................................................ 188 LIST OF TABLES Table Page 1.1 Comparison Ionic and Non-ionic PAGs......................................................... 7 2.1 Other Examples of Iodonium Zwitterions.....................................................
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