Thiol-epoxy "click" chemistry: Application in preparation and postpolymerization modification of polymers

Abstract

Base-catalyzed reaction between a thiol and an epoxide group is a simple fusion process that leads to the formation of a -hydroxythio-ether linkage. This reaction is efficient, regio-selective, and fast. In addition, it produces a reactive hydroxyl group upon completion. Therefore, it is of considerable potential in synthesis of reactive and functional soft materials. Here, we discuss the fundamental aspects of this process, the so-called thiol-epoxy click reaction, and its utility in the preparation and post-polymerization functionalization of polymers and crosslinked networks. Furthermore, its application in surface modification of solid substrates is also considered. Finally, utility of multifunctional materials created using the thiol-epoxy reaction is discussed in the biomedical arena. (c) 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3057-3070