Inspired by mussel adhesive protein: hydrophilic cationic copoly(2-oxazoline)s carrying catecholic side chains,Polymer Chemistry

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Inspired by mussel adhesive protein: hydrophilic cationic copoly(2-oxazoline)s carrying catecholic side chains
Polymer Chemistry ( IF 4.1 ) Pub Date : 2021-08-24 , DOI: 10.1039/d1py00679g
Nils Lüdecke ₁ , Helmut Schlaad ₁

Affiliation

A set of new functionalized poly(2-oxazoline) homopolymers and copolymers carrying protected catecholic side chains were prepared by microwave-assisted cationic ring-opening (co)polymerization. The copolymerizations of 2-ethyl-2-oxazoline with either 2-(3,4-dimethoxyphenyl)-, 2-(3,4-dimethoxybenzyl)-, or 2-(3,4-dimethoxycinnamyl)-2-oxazoline (comonomer ratio 90 : 10) produced gradient or random copolymers with narrow molar mass distributions. During the copolymerization with the 2-(3,4-dimethoxycinnamyl)-2-oxazoline, however, chain coupling reactions occurred at monomer conversions of >50%, supposedly via Michael-type addition of intermediately formed ketene N,O-acetal end groups to 3,4-dimethoxycinnamyl amide side chains. A poly[(2-ethyl-2-oxazoline)-grad-(2-(3,4-dimethoxyphenyl)-2-oxazoline)] was examplarily subjected to partial demethylation and acidic hydrolysis to give a hydrophilic copolymer carrying both catecholic and cationic units, which is designed as a bioinspired adhesive copolymer mimicking mussel adhesive protein.

中文翻译：

受贻贝粘附蛋白的启发：带有儿茶酚侧链的亲水性阳离子共聚（2-恶唑啉）

通过微波辅助阳离子开环（共）聚合制备了一组带有受保护的邻苯二酚侧链的新型官能化聚（2-恶唑啉）均聚物和共聚物。2-乙基-2-恶唑啉与 2-(3,4-二甲氧基苯基)-、2-(3,4-二甲氧基苄基)-或 2-(3,4-二甲氧基肉桂基)-2-恶唑啉（共聚单体）的共聚比率 90:10) 产生具有窄摩尔质量分布的梯度或无规共聚物。然而，在与 2-(3,4-二甲氧基肉桂基)-2-恶唑啉共聚期间，链偶联反应发生在单体转化率 >50% 时，推测是通过中间形成的烯酮 N,O-缩醛端基的迈克尔型加成到 3,4-二甲氧基肉桂基酰胺侧链。聚[(2-乙基-2-恶唑啉)-梯度-(2-(3,4-二甲氧基苯基)-2-恶唑啉)]示例性地进行部分去甲基化和酸性水解，得到带有儿茶酚和阳离子单元的亲水共聚物，该共聚物被设计为模仿贻贝粘附蛋白的仿生粘附共聚物.

更新日期：2021-09-10

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