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University of Florida Thesis Or Dissertation Formatting PRECISE POLYMER END GROUPS, AQUEOUS POLYMERIZATIONS, AND MACROMOLECULAR NANO-AGGREGATES By CHARLES ADRIAN FIGG A DISSERTATION PRESENTED TO THE GRADUATE SCHOOL OF THE UNIVERSITY OF FLORIDA IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY UNIVERSITY OF FLORIDA 2018 © 2018 Charles Adrian Figg To my family and my friends, old and new. ACKNOWLEDGMENTS First, I would like to thank my family. My mother instilled scientific curiosity early in my life and has been my biggest supporter. I am constantly inspired by her resilience and ambition. I appreciate my sister as one of my best friends and for always pushing me to catch up with her successes, and my father and step-father for being beacons of reason and mindfulness. I am grateful to my grandpa, Charles Figg, and my grandmother, Juanita Figg, for teaching me the importance of civil duty and teaching. They fought through adversity to desegregate the public school system and ensure every child in central New Jersey got the education they deserved. Their persistence and unyielding belief in the pursuit and realization of educational goals has guided me though my academic career. I would like to thank Brent Sumerlin for being the mentor I desired and needed. He gave me the freedom to discover my research voice, make mistakes, and learn from my mistakes, while always being insightful and guiding. Brent has taught me not only what it means to be a successful researcher, but a good community member and a patient leader. As I transition from a student to a colleague, I could not be more excited to see what our future collaborations will bring. I also would like to thank my committee, Prof. Daniel A Savin, Prof. Ronald K. Castellano, Prof. Stephen A. Miller, and Prof. Blanka Sharma, for their support during my graduate career. Next, I would like to thank my past academic mentors. I began my science career taking readings on the radioactivity of a parking lot for Dr. Ernst Esch at Los Alamos National Lab. He showed unyielding support of my interests, regardless of if they aligned with his. Prof. Bert Meijer for telling me “it does not matter if my group does 4 what you are interested in, pursue what you want, and I will support you,” and letting me research with Prof. Patricia Dankers because of my interest in biomaterials. Prof. Craig Hawker for letting me join his lab, supporting me whenever I needed life advice, and having me work for one of the most influential mentors I have had, Prof. Brett Fors. Brett taught me the virtue in working hard to achieve and discover and the virtue of investing in the success of others. Prof. Cyrille Boyer for letting me have an Aussie winter holiday in his lab to learn PET-RAFT. Cyrille’s ambition and support for his students have further confirmed my career goals, while his support for me has endured far beyond the ten weeks I worked for him. I could not have done this without the support of my friends. I thank my friends I have known my whole life, Brett, Michelle, and Ariana, for being there to commiserate about our educational goals, especially as we all pursue advanced degrees. I thank my college friends, specifically Michael, Trevor, John, and Ryan, for always planning a Vegas or Napa trip when I needed it. My stammtisch group Nick, Kyle and Georg for the monthly escape of graduate life into the dungeon of Hogan’s. I am grateful to the members of the Sumerlin Group, past and present, for the constant pillar of support and creativity. Specifically, I would like to thank the people I have collaborated with or who have provided immense assistance in my research: Nick, Tomo, Georg, Megan, Jacob, Becky, Soma, Jimmy, John, and Bryan, I would also like to thank my many collaborators for their assistance in completing our research goals: Prof. Daniel Savin, Prof. Ronald Castellano, Prof. Cyrille Boyer, Prof. Zesheng An, Prof. Nathan Gianneschi, Prof. David Haddleton, Dr. Alexandre Simula, Kalkidan Gebre, Dr. Kyle Bentz, Dr. Sivaprakash Shanmugam, Dr. Ashton Bartley, and Molly Touve. 5 Finally, I would like to thank Heather Drew. She inspires me every day, and I could not imagine anyone else to chase dreams with. 6 TABLE OF CONTENTS page ACKNOWLEDGMENTS ...................................................................................................... 4 LIST OF TABLES .............................................................................................................. 12 LIST OF FIGURES ............................................................................................................ 13 LIST OF ABBREVIATIONS ............................................................................................... 17 ABSTRACT ........................................................................................................................ 20 CHAPTER 1 BACKGROUND .......................................................................................................... 22 1.1 Precise Bond Formation ....................................................................................... 23 1.2 Precise Polymer Synthesis ................................................................................... 23 1.2.1 Catalyst-Free RAFT Photopolymerizations ................................................ 24 1.2.2 Externally-Initiated RAFT Photopolymerizations ....................................... 26 1.2.3 Photoinduced Electron/Energy Transfer (PET) RAFT Polymerizations .... 28 1.3 Precise Nanoscale Interactions ............................................................................ 31 2 RESEARCH OBJECTIVE ........................................................................................... 35 3 EFFICIENT AND CHEMOSELECTIVE SYNTHESIS OF OMEGA, OMEGA- HETERODIFUNCTIONAL POLYMERS..................................................................... 38 3.1 Introduction ........................................................................................................... 38 3.2 Results and Discussion ........................................................................................ 40 3.3 Conclusion ............................................................................................................ 47 3.4 Materials and Methods ......................................................................................... 47 3.4.1 Materials ...................................................................................................... 47 3.4.2 Characterization .......................................................................................... 48 3.4.3 End-Group Functionalization of mPEG to Dichlorotriazine-mPEG ........... 48 3.4.4 2-Furylmethanethiol Conjugation to 2-mPEG-4,6-dichloro-1,3,5- triazine ............................................................................................................... 49 3.4.5 4-Benzylpiperidine Conjugation to 2-mPEG-4-(2-furylmethanethiol)-6- chloro-1,3,5-triazine .......................................................................................... 49 3.4.6 Phenylmethanethiol Conjugation to 2-mPEG-4-(2-furylmethanethiol)- 6-chloro-1,3,5-triazine ....................................................................................... 49 3.4.7 1-Phenylmethanamine Conjugation to 2-mPEG-4-(2- furylmethanethiol)-6-chloro-1,3,5-triazine ........................................................ 50 3.4.8 Phenylmethanol Conjugation to 2-mPEG-4-(2-furylmethanethiol)-6- chloro-1,3,5-triazine .......................................................................................... 50 7 3.4.9 1-(2-Furyl)methylamine Conjugation to 2-mPEG-4,6-dichloro-1,3,5- triazine ............................................................................................................... 50 3.4.10 4-Benzylpiperidine Conjugation to 2-mPEG-4-[1-(2- furyl)methylamine]-6-chloro-1,3,5-triazine ....................................................... 51 3.4.11 Phenylmethanethiol Conjugation to 2-mPEG-4-[1-(2- furyl)methylamine]-6-chloro-1,3,5-triazine ....................................................... 51 3.4.12 1-Phenylmethanamine Conjugation to 2-mPEG-4-[1-(2- furyl)methylamine]-6-chloro-1,3,5-triazine ....................................................... 51 3.4.13 Phenylmethanol Conjugation to 2-mPEG-4-[1-(2-furyl)methylamine]- 6-chloro-1,3,5-triazine ....................................................................................... 52 3.4.14 2-Furanmethanol Conjugation to 2-mPEG-4,6-dichloro-1,3,5-triazine.... 52 4 MILD AND EFFICIENT SYNTHESIS OF OMEGA, OMEGA- HETERODIFUNCTIONALIZED POLYMERS AND POLYMER BIOCONJUGATES ..................................................................................................... 53 4.1 Introduction ........................................................................................................... 53 4.2 Results and Discussion ........................................................................................ 55 4.2.1 Conjugating BTF to mPEG-amine .............................................................. 55 4.2.2 Synthesizing Omega, Omega-Homodifunctional Polymers ..................... 55 4.2.3 Synthesizing Omega, Omega-Heterodifunctional Polymers ..................... 57 4.2.4 Conjugating Omega, Omega-Heterodifunctional Polymers to Avidin ....... 60 4.3 Conclusions .......................................................................................................... 61 4.4 Materials and Methods ......................................................................................... 62 4.4.1
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