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研究生： 謝宜良
Hsieh, Yi Liang
論文名稱： 有機金屬錯合物在開環與可控/活性自由基聚合的應用
Development of Organometallic Complexes for Ring-opening and Controlled / Living Radical Polymerization
指導教授： 彭之皓
Peng, Chi How
口試委員: 韓建中
王潔
陳俊太
王建隆
彭之皓
學位類別： 博士
Doctor
系所名稱： 理學院 - 化學系
Department of Chemistry
論文出版年： 2015
畢業學年度： 103
語文別： 英文
論文頁數： 285
中文關鍵詞： 開環聚合反應 、可控自由基聚合反應 、聚酯類高分子
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    • Cobalt complexes mediated radical polymerization (CMRP) and ring-opening polymerization (ROP) are the most tools of modern controlled / living polymerization. CMRP is recognized by its unique control efficiency to vinyl acetate (VAc), which shows important applications in materials science and medical biology but can hardly be controlled by other living radical polymerization (LRP) methods. ROP is the major technique to synthesize biocompatible and biodegradable polyesters materials with low polydispersity (PDI = Mw/Mn) and well-controlled molecular weight. Initiators or catalysts used in ring-opening polymerization are required to have a high reactivity, negligible toxicity, low cost, and capability to lead a high degree of polymerization. In this regard, this thesis describes new organometallic complexes that focus on the mediate vinyl olefins and cyclic esters monomers, which were successfully achieve by CMRP and ROP systems. Building various copolymers with different components are also effectively synthesized through CMRP and ROP methods. For better understanding, I divided this thesis into four chapters. The chapter 1 to 3 describe about ROP catalyzed / initiated by newly metal complexes and discuss steric and electronic effect on ligands. In addition, the stereoselectivity of rac-lactide polymerization is the important topic in Al complexes system. Last chapter illustrate about polymerization of various vinyl olefins and block copolymer synthesis mediated by cobalt bipyridine-bisphenolate complex (CoII(BpyBph)).

    Cobalt complexes mediated radical polymerization (CMRP) and ring-opening polymerization (ROP) are the most tools of modern controlled / living polymerization. CMRP is recognized by its unique control efficiency to vinyl acetate (VAc), which shows important applications in materials science and medical biology but can hardly be controlled by other living radical polymerization (LRP) methods. ROP is the major technique to synthesize biocompatible and biodegradable polyesters materials with low polydispersity (PDI = Mw/Mn) and well-controlled molecular weight. Initiators or catalysts used in ring-opening polymerization are required to have a high reactivity, negligible toxicity, low cost, and capability to lead a high degree of polymerization. In this regard, this thesis describes new organometallic complexes that focus on the mediate vinyl olefins and cyclic esters monomers, which were successfully achieve by CMRP and ROP systems. Building various copolymers with different components are also effectively synthesized through CMRP and ROP methods. For better understanding, I divided this thesis into four chapters. The chapter 1 to 3 describe about ROP catalyzed / initiated by newly metal complexes and discuss steric and electronic effect on ligands. In addition, the stereoselectivity of rac-lactide polymerization is the important topic in Al complexes system. Last chapter illustrate about polymerization of various vinyl olefins and block copolymer synthesis mediated by cobalt bipyridine-bisphenolate complex (CoII(BpyBph)).

    ABSTRACT III LIST OF PUBLICATION IV Background of Ring-Opening Polymerization (ROP) 1 CHAPTER 1 7 1.1 Abstract 8 1.2 Introduction 8 1.3 Results and Discussion 10 1.3.1 Synthesis and characterization of Zn complexes 10 1.3.2 Ring-Opening Polymerization of -caprolactone, -butyrolactone, and -valerolactone. 14 1.3.3 Ring-Opening Polymerization of L-lactide and rac-lactide 19 1.3.4 Chain extension of -CL with -BL and -VL 23 1.4 Mechanism 26 1.5 Conclusions 27 1.6 Experimental Section 28 1.7 Reference 35 CHAPTER 2 39 2.1 Abstract 40 2.2 Introduction 40 2.3 Results and Discussion 43 2.3.1 Synthesis and characterization of aluminum complexes 43 2.3.2 Ring-Opening Polymerization of -caprolactone 45 2.3.3 Ring-Opening Polymerization of L-lactide and rac-lactide 52 2.3.4 Formation of PCL-b-PLA block copolymer 58 2.4 Mechanism 59 2.5 Conclusion 67 2.6 Experimental Section 69 2.7 Reference 77 CHAPTER 3 80 3.1 Abstract 81 3.2 Introduction 82 3.3 Results and Discussion 83 3.3.1 Synthesis and characterization of Zn and Al complexes 83 3.3.2 Ring-Opening Polymerization of -caprolactone 87 3.3.3 Ring-Opening Polymerization of L-lactide and rac-lactide 93 3.3.4 Synthesis of copolymers 99 3.4 Conclusions 105 3.5 Experimental Section 106 3.6 Reference 118 CHAPTER 4 121 4.1 Abstract 122 4.2 Introduction 122 4.3 Results and Discussion 127 4.3.1 Synthesis of BpyBph ligand and cobalt complex 127 4.3.2 Polymerization of vinyl acetate 128 4.3.3 Polymerization of methyl acrylate 136 4.3.4 Polymerization of other monomers 140 4.3.5 Synthesis of block copolymer 142 4.4 Conclusion 144 4.5 Experimental Section 145 4.6 Reference 148

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