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Synthesis and characterization of polymers incorporating N-alkyl urea-peptoid sequences.

机译：包含N-烷基脲-类肽序列的聚合物的合成和表征。

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摘要

This dissertation is mainly based on the works of synthesis and characterization of polymer/N-alkyl urea peptoid hybrid materials. Polymers were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization using thrithiocarbonate and dithiocarbonate chain transfer agents in controlled manner. Poly(N-alkyl urea peptoid) was synthesized via step growth polymerization using symmetric diamine and diisocyanate. N-Alkyl urea peptoid sequences up to sixmer were synthesized through three steps repetition cycles in good yields. Several different polymeric materials were explored combining the three different material synthetic strategies including polymer conjugates shown in chapter 2, molecular brushes shown in chapter 3, water soluble A-B-A triblock copolymer shown in chapter 4. Firstly, two well-defined statistical copolymers poly(styrene-co-3-azidopropyl methacrylate) and poly(3-O-methacryloyl-1,2:5,6-di-O-isopropylidene-D-glucofuranose-co-AzPMA) were synthesized by RAFT. An exemplary N-alkyl urea peptoid trimer was synthesized and conjugated to the two copolymers through the 'click' reaction of the azide pendent group of polymers with the complilanry alkene group at N-alkyl urea peptoid. The polymer conjugates were subjected to further post-modification to generated fluorescent conjugates or water soluble materials. Following the explore of conjugation, N-alkyl urea peptoid was used as comonomer to synthesize linear poly(N-alkyl urea peptoid). The RAFT agent was introduced onto the linear polymer generated by step growth polymerization once again through 'click' reaction. Sequentially, styrene and tert-butyl acrylate was grown from RAFT agents sites that fused onto the poly(N-alkyl urea peptoid) backbone to make block copolymer arms. Upon removal of the tert-butyl groups, the molecular brushes were observed to generate micelles in aqueous solution. The self-assembly N-alkyl urea peptoid was then investigated and conjugated to water soluble polymer poly(ethylene glycol) to produce a A-B-A block copolymer that self-assembled into ribbons in aqueous solution. The final two part of dissertation was about gelling materials studies starting with presenting a synthesis strategy for low molecular weight organogelators (LMOG) using the ureidopyrimidinone (UPy) group functioned N-alkyl urea peptoid. The surprising observation of gelation in DMSO led to extensive investigation of the gelification mechanism studies. Based on the lessons of LMOG, the copolymerization of different Tg monomers with quadruple hydrogen bonding containing methacrylate was demonstrated suitable to produce polymeric organogelators in the final chapter.
机译：本文主要基于聚合物/ N-烷基脲类肽杂化材料的合成与表征。通过可逆的加成-断裂链转移（RAFT）聚合，使用硫代碳酸氢盐和二硫代碳酸氢盐链转移剂以受控方式合成聚合物。通过使用对称二胺和二异氰酸酯的逐步生长聚合合成聚（N-烷基脲类肽）。通过三步重复循环以高收率合成了高达六聚体的N-烷基脲类肽序列。探索了几种不同的聚合物材料，结合了三种不同的材料合成策略，包括第2章中显示的聚合物共轭物，第3章中显示的分子刷，第4章中显示的水溶性ABA三嵌段共聚物。首先，两种定义明确的统计共聚物聚（苯乙烯-通过RAFT合成了甲基丙烯酸三-3-叠氮基丙基）和聚（3-O-甲基丙烯酰基-1,2：5,6-二-O-异亚丙基-D-葡萄糖呋喃糖-co-AzPMA）。合成了示例性的N-烷基脲类肽三聚体，并通过聚合物的叠氮侧基与在N-烷基脲类肽中的互补链烯基的“点击”反应与两种共聚物共轭。使聚合物缀合物进行进一步的后改性以产生荧光缀合物或水溶性材料。在探索共轭之后，将N-烷基脲类肽用作共聚单体以合成线性聚（N-烷基脲类肽）。将RAFT剂再次通过“点击”反应引入到通过逐步生长聚合产生的线性聚合物上。顺序地，从RAFT剂位点生长苯乙烯和丙烯酸叔丁酯，这些位点融合到聚（N-烷基脲类肽）骨架上，制成嵌段共聚物臂。除去叔丁基后，观察到分子刷在水溶液中产生胶束。然后研究了自组装的N-烷基脲类肽，并将其与水溶性聚合物聚（乙二醇）偶联，生成了A-B-A嵌段共聚物，该共聚物在水溶液中自组装成带状。论文的最后两部分是关于胶凝材料的研究，首先提出了使用脲基嘧啶酮（UPy）基团作用的N-烷基脲类肽的低分子量有机胶凝剂（LMOG）的合成策略。 DMSO中令人惊讶的凝胶化观察导致了对凝胶化机理研究的广泛研究。根据LMOG的经验，在最后一章中，证明了不同的Tg单体具有四重氢键合的含甲基丙烯酸酯的共聚反应适合生产聚合物有机胶凝剂。

著录项

  • 作者

    Chen, Xiaoping.;

  • 作者单位

    University of Cincinnati.;

  • 授予单位 University of Cincinnati.;
  • 学科 Chemistry Polymer.;Engineering Materials Science.
  • 学位 Ph.D.
  • 年度 2013
  • 页码 194 p.
  • 总页数 194
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类
  • 关键词

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