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含L-氨基酸基团的手性功能单体及与N-异丙基丙烯酰胺共聚物的合成

时东新,陈娇娇*,杜显丽,王乐乐,蒋奕,任绒绒   

  1. (天津工业大学环境与化学工程学院 天津 300387)
  • 收稿日期:2012-09-05 修回日期:2012-12-10 出版日期:2013-07-10 发布日期:2013-07-10
  • 通讯作者: 陈娇娇，副教授; Tel/Fax:022-83955723; E-mail:chenjiaojiao@tjpu.edu.cn; 研究方向：生物医药新材料
  • 基金资助:
    国家自然科学基金(20904039)天津市应用基础及前沿技术研究计划(10JCYBJC02900)资助项目

Synthesis of Chiral Functional Monomers Containing L-Amino Acid Groups and Their Copolymers with N-isopropylacrylamide

SHI Dongxin, CHEN Jiaojiao*, DU Xianli, WANG Lele, JIANG Yi, REN  Rongrong   

  1. (School of Environmental and Chemical Engineering,Tianjin Polytechnic University,Tianjin 300387,China)
  • Received:2012-09-05 Revised:2012-12-10 Published:2013-07-10 Online:2013-07-10
  • Contact: Chen Jiaojiao

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摘要： 以L-苯丙氨酸（L-Phe）、L-色氨酸（L-Trp）和L-亮氨酸（L-Leu）3种常见的氨基酸为手性源，经过酯化、缩合等步骤制备3种手性功能单体AAc-L-Phe(AAc:丙烯酸)、AAc-L-Trp和AAc-L-Leu，其结构经过IR、1H NMR确证。 并将手性单体AAc-L-Phe与温敏材料N-异丙基丙烯酰胺(NIPAam)共聚，制备了手性共聚物P(NIPAam-co-AAc-L-Phe)，结构经IR确证，示差扫描量热分析测试证明其具有温敏性。 这些手性功能单体有可能用于制备环境响应性手性高分子聚合物。

关键词: 手性, L-氨基酸, 合成, 功能单体, 共聚物

Abstract: Three chiral functional monomers containing L-phenylalanine(L-Phe), L-tryptophane(L-Trp) and L-leucine(L-Leu) were designed and synthesized and used as precursors for preparing of chiral polymers. After esterification and condensations, AAc-L-Phe(AAc:acrylic acid), AAc-L-Trp and AAc-L-Leu were obtained and characterized by IR and 1H NMR. Then the subsequent copolymerization between AAc-L-Phe and N-isopropylacrylamide(NIPAam) was carried out in different mass ratio. The resulted polymers were identified by IR and differential scanning calorimetry(DSC) and proved that all of them are optical active and thermo-sensitive materials. The successful synthesis of chiral polymers suggested that these chiral monomers can be applied to the preparation of chiral polymers.

Key words: chiral, L-amino acids, synthesis, Functional monomer, copolymer

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