Selective ring-opening polymerization of glycidyl esters: a versatile synthetic platform for glycerol-based (co)polyethers,Polymer Chemistry

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Selective ring-opening polymerization of glycidyl esters: a versatile synthetic platform for glycerol-based (co)polyethers
Polymer Chemistry ( IF 4.1 ) Pub Date : 2022-05-20 , DOI: 10.1039/d2py00551d
Shan Liu ₁ , Lijun Liu ₁ , Yubo Zhou ₁ , Ye Chen ₁ , Junpeng Zhao _{1,

2}

Affiliation

Linear polyglycerols are highly valued for their excellent hydrophilicity and biocompatibility as well as their multihydroxy nature. We report here a convenient route for the controlled synthesis of polyglycerols through ring-opening polymerization (ROP) of commercialized glycidyl butyrates (GBs). Starting from enantiopure GBs, well-defined poly(glycidyl ester)s with controlled molar mass and stereoregularity are achieved thanks to the chemoselectivity of the bicomponent metal-free catalyst that prevents both transesterification and epimerization. The pendant butyrate groups are readily cleaved by organobase-catalyzed methanolysis, yielding linear polyglycerols that inherit isotacticity and regioregularity from the parent polymers. Copolymerization of SGB and propylene oxide occurs in a random manner resulting in a series of narrowly distributed copolyethers with a precisely regulated number of pendant hydroxyl groups to afford tunable aqueous thermosensitivity. The method is further extended to construct polyglycerol-based amphiphilic and double-hydrophilic copolyethers by block copolymerization of RGB with tert-butyl glycidyl ether and ethylene oxide, respectively.

中文翻译：

缩水甘油酯的选择性开环聚合：甘油基（共）聚醚的多功能合成平台

线性聚甘油因其优异的亲水性和生物相容性以及多羟基性质而受到高度评价。我们在此报告了一种通过商业化缩水甘油酯 (GBs) 的开环聚合 (ROP) 控制合成聚甘油的便捷途径。从对映纯GB开始，由于双组分无金属催化剂的化学选择性可防止酯交换和差向异构化，因此可以实现具有受控摩尔质量和立体规整性的定义明确的聚缩水甘油酯。丁酸侧基很容易被有机碱催化的甲醇分解裂解，产生线性聚甘油，其继承了母体聚合物的全同立构规整性和区域规整性。S的共聚GB 和环氧丙烷以随机方式发生，产生一系列分布窄的共聚醚，具有精确调节数量的侧羟基，从而提供可调的水热敏感性。该方法进一步扩展到分别通过R GB 与叔丁基缩水甘油醚和环氧乙烷的嵌段共聚来构建基于聚甘油的两亲和双亲水共聚醚。

更新日期：2022-05-20

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