Issue 24, 2022

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
28 Eph 2022
Accepted
20 Mey 2022
First published
20 Mey 2022

Polym. Chem., 2022,13, 3650-3659

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

S. Liu, L. Liu, Y. Zhou, Y. Chen and J. Zhao, Polym. Chem., 2022, 13, 3650 DOI: 10.1039/D2PY00551D

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