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Sustainable Polymers and Antimicrobial Biomaterials from Multicyclic Natural Products Md Anisur Rahman

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Sustainable Polymers and Antimicrobial Biomaterials from Multicyclic Natural Products Md Anisur Rahman University of South Carolina Scholar Commons Theses and Dissertations Spring 2019 Sustainable Polymers and Antimicrobial Biomaterials from Multicyclic Natural Products Md Anisur Rahman Follow this and additional works at: https://scholarcommons.sc.edu/etd Part of the Chemistry Commons Recommended Citation Rahman, M. A.(2019). Sustainable Polymers and Antimicrobial Biomaterials from Multicyclic Natural Products. (Doctoral dissertation). Retrieved from https://scholarcommons.sc.edu/etd/5137 This Open Access Dissertation is brought to you by Scholar Commons. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of Scholar Commons. For more information, please contact [email protected]. SUSTAINABLE POLYMERS AND ANTIMICROBIAL BIOMATERIALS FROM MULTICYCLIC NATURAL PRODUCTS by Md Anisur Rahman Bachelor of Science Jahangirnagar University, 2011 Master of Science Tennessee State University, 2014 Submitted in Partial Fulfillment of the Requirements For the Degree of Doctor of Philosophy in Chemistry College of Arts and Sciences University of South Carolina 2019 Accepted by: Chuanbing Tang, Major Professor Brian C. Benicewicz, Committee Member Mythreye Karthikeyan, Committee Member Alan W. Decho, Committee Member Cheryl L. Addy, Vice Provost and Dean of the Graduate School © Copyright by Md Anisur Rahman, 2019 All Rights Reserved. ii DEDICATION To my parents, for their love, support, lifelong sacrifices and guiding me to get the best education possible. To Moumita Sharmin Jui, my loving wife, for her enormous love, care and support. None of my accomplishments would be possible without her support. iii ACKNOWLEDGEMENTS First and foremost, I would like to convey my sincere gratitude to my advisor, Dr. Chuanbing Tang, who gave me the opportunity to work in his research group and offered me tremendous support and guidance on my research projects throughout my Ph.D. journey. It has been a great honor and a privilege for me to work under such an enthusiastic and knowledgeable person. His passion and enthusiasm for polymer science has made an enormous impact on me and motivated me to develop as a polymer scientist. I sincerely thank his contributions to make my Ph.D. experience diverse, productive and stimulating. I want to appreciate him for being an excellent role model as a successful professor and a caring person that made a positive impact on my life. Then I would like to thank my graduate committee members Dr. Brian Benicewicz, Dr. Alan W. Decho and Dr. Mythreye Karthikeyan for their advice, encouragement, and valuable suggestions on my research during graduate school. I also appreciate my committee chair Dr. Brian Benicewicz for being a great teacher in the introduction to polymer that creates the foundation of my polymer science knowledge. I want to thank Dr. Decho and his group members Dr. Yunpin Chen and Dr. Kristen Miller for their collaborations with our group. In addition, I want to mention Dr. Mitzi Nagarkatti and her group member Dr. Marpe Bam for his productive collaborations. Further, I would like to acknowledge Dr. Morgan Stefik and his students especially Nadee, Amrita and Zach for helping me to run SAXS and allowing me to use their SAXS instrument. iv I am very appreciative of the experiences shared and friendships formed with other graduate students, post-docs and visiting scholars during the last 4.5 years at USC. I want to appreciate and mention the members of Tang Polymer Group. I thank Dr. Mitra Ganewatta and Dr. Liang Yuan for being my graduate mentor during the early stages of my graduate career. I had an opportunity to work and learn a lot of research techniques from some hard-working and motivating post-doctoral scientist such as Dr. Zhongkai, Dr. Jifu Wang, and Dr. Ye Sha, and I am thankful to them. It was a pleasant experience for me to work with Shichao Xu, Shaobo Tan, and Haijiao Kang. Thank you, Meghan E. Lamm, Tianyu Zhu, Yujin Cha and Pabel Kabir for being nice friends. Edgar Luat was excellent undergraduate students who worked with me. I also want to mention Dr. Perry Wilbon, Dr. Jeffery Hayat, Dr. Peng Yang, Dr. Hui Li, Nathen Trenor, Paras Pageni, Xinzhou Zhang, Ryan J. Miskin, Lin Fu, Jihyeon Hwang, Leman Kurnaz and many others. It is a great pleasure to work with all of you and learn from you. Thanks for all your help and suggestions. Besides the exciting research work, I feel thankful to get the chance to work with Dr. Brian Benicewicz while I served as the secretary of the ACS Poly/PMSE Student Chapter at USC. I want to mention Mitra, Julia, Andrew and Nadee for working with me to conduct many projects. Further, I want to give my sincerest gratitude to my mother, my father, other family members and friends for their unconditional love and support. I also would like to thank my wife Moumita Sharmin Jui for her constant support, patience, and help throughout my graduate school career. Finally, I would like to acknowledge all the funding supports from the University of South Carolina, and the National Science Foundation (NSF). v ABSTRACT In this dissertation, the development of sustainable polymers and antimicrobial biomaterials from multicyclic natural products is illustrated. In Chapter 1, an overall background and recent development of sustainable polymers from natural product-based renewable biomass, antimicrobial biomaterials, and polymerization methods are introduced. Afterward, the primary research objectives of my doctoral research work are illustrated. In chapter 2, designing block copolymer architectures toward tough bioplastics from renewable natural rosin was described. One of the most abundant natural biomasses is resin acids, however, most of the polymers derived from resin acids are brittle because of their bulky hydrophenanthrene pendant group. To overcome the brittleness, rosin containing pentablock and triblock copolymers were synthesized through living sequential ring opening metathesis polymerization (ROMP). Their thermal and mechanical properties were investigated. The phase behaviors were also studied for the microphase-separated pentablock and triblock copolymers using small angle x-ray scattering (SAXS) and atomic force microscopy. A new class of true facial amphiphilic cationic antimicrobial polymers was illustrated in chapter 3. Facially amphiphilic antimicrobial polymers were prepared from multicyclic natural products (e.g. bile acids) via reversible-addition fragmentation chain transfer (RAFT) polymerization. The antimicrobial activity against a range of bacteria and vi hemolysis activity with mammalian cells is investigated. In addition, the antimicrobial mechanistic aspects of facially amphiphilic polymers were also illustrated. Chapter 4 is explained about the facial amphiphilicity-induced self-assembly (FAISA) of multicyclic natural product-based cationic copolymers. The detail self-assembly behavior of copolymers with different polyethylene glycol was explained. The self-assembly of these copolymers to form antimicrobial nanoparticles was investigated in Chapter 5. The nanoaggregates exhibited strong antimicrobial activity against Gram-negative bacteria and showed minimal toxicity against mammalian cell. Finally, a summary and future directions of this dissertation research are provided in chapter 6. In future work, some suggestions about future directions involving renewable biomass for sustainable development are given. vii TABLE OF CONTENTS DEDICATION ....................................................................................................................... iii ACKNOWLEDGEMENTS ........................................................................................................ iv ABSTRACT .......................................................................................................................... vi LIST OF TABLES .................................................................................................................. xi LIST OF FIGURES ................................................................................................................ xii LIST OF SYMBOLS ............................................................................................................. xvi LIST OF ABBREVIATIONS .................................................................................................. xvii CHAPTER 1 GENERAL INTRODUCTION ...................................................................................1 1.1 SUSTAINABLE POLYMERS FROM NATURAL PRODUCT-BASED BIOMASS ................2 1.2 RENEWABLE RESIN ACIDS .....................................................................................5 1.3 BILE ACIDS ............................................................................................................7 1.4 ANTIMICROBIAL POLYMERS ................................................................................10 1.5 SELF-ASSEMBLY OF AMPHIPHILIC POLYMERS .....................................................13 1.6 POLYMERIZATION TECHNIQUES...........................................................................14 1.7 RESEARCH OBJECTIVES ........................................................................................17 1.8 REFERENCES ........................................................................................................18 CHAPTER 2 DESIGNING BLOCK COPOLYMER ARCHITECTURES TOWARD TOUGH BIOPLASTICS FROM NATURAL ROSIN .......................................................................................................27 2.1 ABSTRACT ...........................................................................................................28
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