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NOVEL Π-CONJUGATED MATERIALS PLUS THEIR CHARACTERIZATIONS and APPLICATIONS Xiuxian He Clemson University, [email protected]

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NOVEL Π-CONJUGATED MATERIALS PLUS THEIR CHARACTERIZATIONS and APPLICATIONS Xiuxian He Clemson University, Susanhe18@Yahoo.Com Clemson University TigerPrints All Dissertations Dissertations 7-2010 NOVEL π-CONJUGATED MATERIALS PLUS THEIR CHARACTERIZATIONS AND APPLICATIONS Xiuxian He Clemson University, [email protected] Follow this and additional works at: https://tigerprints.clemson.edu/all_dissertations Part of the Polymer Chemistry Commons Recommended Citation He, Xiuxian, "NOVEL π-CONJUGATED MATERIALS PLUS THEIR CHARACTERIZATIONS AND APPLICATIONS" (2010). All Dissertations. 611. https://tigerprints.clemson.edu/all_dissertations/611 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]. NOVEL π-CONJUGATED MATERIALS PLUS THEIR CHARACTERIZATIONS AND APPLICATIONS A Thesis Presented to the Graduate School of Clemson University In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy Analytical Chemistry by Xiuxian Susan He July, 2010 Accepted by: Dr. Rhett C. Smith, Committee Chair Dr. Jason McNeill Dr.Jeffrey Anker Dr. Shiou-Jyh Hwu i ABSTRACT The theme of this dissertation will focus on the syntheses and characterization of bipyridine (bipy) containing π-conjugated polymers (CPs). Specifically, poly(p- phenylene ethynylene), polyfluorene and poly(p-phenylene vinylene) derivatives have been prepared via Sonogashira coupling, Suzuki coupling and Heck coupling, respectively. Derivatives of poly(p-phenylene ethynylene), polyfluorene and poly(p- phenylene vinylene) are known to have applications in optical and electronic devices. Through this study, polymers condensed with bulky bipy-containing TAB as one of the copolymer units have shown increased solubility and diminished intrachain/interchain aggregation in solution and in film due to the effectiveness of TAB in controlling the relative orientations of individual polymer chains. The effect of transition metal binding on polymer photophysics have been quantified and monitored by absorption and fluorescence spectroscopy. This series of metallopolymers features optical estimated bandgaps (Eg) of less than 3 eV, revealing their potential applications as light emitting diode and photovoltaic materials. ii DEDICATION I dedicate this work to my family, my Mom, my Dad, my brother Joe He and his wife Yao He. This thesis will complete because of their continuous support. To my parents, it‟s them take care of me financially and physically. Make me feel like I am the luckiest person in the world and the best way to say thank you is to graduate from school. To my brother and his wife, their courage toward life strongly boots my confidence to my future; provide me a good example and attitudes to face the obstacles in my life. To my best friends, Jason Huang, Fenghai Guo, Man Zhou, Hongyu Chen and everyone from the church, for their constant support. I wouldn‟t be happier without their listening. To my labmates, Brad and Anshuman my stay in Clemson could be a lot more complicate without their understanding and help. To my friend and collaborator, Manuel N. Chaur, we had a good time to study all these three hard classes together and thanks a lot with your help in CVs. It‟s your unbeatable manner toward life, make me deeply understand “there is always more solution than problem”. iii ACKNOWLEDGMENTS I need to thank many persons for their support, advices, and help during my student career. These persons have offered great help and encouragement for me to pursue my Ph.D, complete my Ph.D and use my Ph.D after I graduate. The first person is my undergraduate advisor Dr. Daniel Rabinovich, without his encouragement to presume graduate study; I probably stop school many years ago. I also owe many thanks to my current advisor Dr. Rhett C. Smith for his wise advices, his patience, his kindness, his time, his support and his help to me for the past four years. He is a person devotes all he has to his group and fortunately, I am part of his group. Dr. Jeffrey Anker, Dr. Jason McNeill and Dr. Shiou-Jyh Hwu are my committee members; I thank them for their valuable comments and questions for pre-oral and defense. I also need to thank them for their time to attend my pre-oral and defense. This thesis will not be possible without their signature. To the Smith group, especially Brad Morgan, Anshuman Mangalum, I really appreciate your help, your comments, and understanding in many ways. At the end, I would like to thank Clemson chemistry department offered me the opportunity to study here. iv TABLE OF CONTENTS Page TITLE PAGE .................................................................................................................... i ABSTRACT ..................................................................................................................... ii DEDICATION ................................................................................................................ iii ACKNOWLEDGMENTS .............................................................................................. iv LIST OF TABLES ......................................................................................................... vii LIST OF FIGURES ...................................................................................................... viii LIST OF SCHEMES........................................................................................................ x LIST OF CHARTS ......................................................................................................... xi LIST OF SYMBOLS AND ABBREVIATIONS .......................................................... xii CHAPTER I. INTERACTIONS OF ORGANIC MATERIALS WITH LIGHT ................. 1 Origins of light absorbing species in organic electronic materials .......... 1 Extent of π–conjugation and its effects on bandgap ................................ 2 Applications of π–conjugated polymers .................................................. 3 From insulators to semiconductors-explanation from band theory ......... 4 What happens when a molecule get excited ............................................ 6 Excitons-transporter of energy between ground and excited states ......... 9 Basic operation principles behind (O)LEDs .......................................... 11 Basic mechanisms of organic solar cells ............................................... 14 Applications of conjugated polymers in biosensing .............................. 16 Polymers of interest ............................................................................... 17 Different types of polymers feature conductivity .................................. 18 π–conjugated poly(p-phenylene ethynylene) derivatives ...................... 20 π–conjugated poly(fluorene) derivatives ............................................... 22 v II. A BIPYRIDYL CHROMOPHORE-MODIFIED SEMIFLUORINATED POLYMER ...................................................... 25 Introduction ............................................................................................ 25 Results and Discussion .......................................................................... 27 Conclusions ............................................................................................ 38 III. STERIC COORDINATION CONTROL IN CONDUCTING POLYMERS ............................................................... 53 Introduction ............................................................................................ 53 Results and Discussion .......................................................................... 57 IV. POTENTIAL BIOSENSOR FOR PHOSPHATE IONS ............................. 85 Phosphate ions in biological system ...................................................... 86 Results and discussion ........................................................................... 89 Conclusions ............................................................................................ 96 V. CONCLUSIONS AND FUTURE DIRECTIONS....................................... 98 REFERENCES ............................................................................................................ 100 COPYRIGHT PERMISSIONS .................................................................................... 110 APPENDICES ............................................................................................................. 120 A: NMR spectra .............................................................................................. 120 B: UV-vis and photoluminescence spectra ..................................................... 143 C: Single crystal X-ray diffraction structure .................................................. 229 vi LIST OF TABLES Table Page 2.1 Dissociation constants and photoluminescent quenching characteristics of P1 ............................................................................... 31 3.1 Select Photophysical Properties of Polymers .............................................. 63 3.3 Electrochemical and Band Gap Data ........................................................... 68 4.1 Absorption data and photos demonstrating the range of colorimetric responses ........................................................................... 91 vii LIST OF FIGURES Figure Page 1.1 Schematic representation of relative orbital energies in a generic organic molecule ......................................................................... 2 1.2 Jablonski diagram of organic molecules
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