Diversely Substituted Polyamide Structures through Thiol–Ene Polymerization of Renewable Thiolactone Building Blocks
Diversely Substituted Polyamide Structures through Thiol–Ene Polymerization of Renewable Thiolactone Building Blocks
复制标题
DOI：
10.1021/ma4022423
复制
发表时间：
2014-01
期刊：
影响因子：
5.5
通讯作者：
F. Goethals;Steven A. Martens;Pieter Espeel;O. V. D. Berg;F. D. Prez
中科院分区：
文献类型：
--
作者：
F. Goethals;Steven A. Martens;Pieter Espeel;O. V. D. Berg;F. D. Prez
采用10-十一烯酸的硫内酯衍生物作为可再生的AB '单体，一锅法合成了不同取代的聚酰胺结构，在聚合物的主链和侧链上都含有酰胺基团。硫内酯实体的亲核氨解释放出硫醇，该硫醇进一步在逐步的硫烯光聚合反应中反应。使用不同的伯胺，得到了几种结构各异的聚酰胺，其物理性质取决于侧链的长度和化学性质。聚合后，聚合物主链上的硫化物键与相应的亚砜和砜的氧化改变了材料，氧化程度对最终的机械性能有影响。此外，这种温和而直接的聚合方法被应用于功能性聚合物网络的合成。
A thiolactone derivative of 10-undecenoic acid was used as a renewable AB′ monomer for the one-pot synthesis of diversely substituted polyamide structures, containing amide moieties both in the polymer backbones and in their side chains. Nucleophilic aminolysis of the thiolactone entity liberates a thiol, which further reacts in a stepwise thiol–ene photopolymerization reaction. Using different primary amines, several structurally diverse polyamides, with physical properties dependent on the length and chemical identity of the side chain, were obtained. Postpolymerization oxidation of the sulfide linkages in the polymer backbone to their corresponding sulfoxides and sulfones altered the material, with the degree of oxidation having an impact on the final mechanical properties. Furthermore, this mild and straightforward polymerization procedure was applied for the synthesis of functional polymer networks.