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 β‐hydroxythio‐ether linkage. This reaction is efficient, regio‐selective, and fast. In addition, it produces a reactive hydroxyl group upon completion. Therefore, it is o...

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Bibliographic Details
Published in:Journal of polymer science. Part A, Polymer chemistry Polymer chemistry, 2016-10, Vol.54 (19), p.3057-3070
Main Authors: Stuparu, Mihaiela C., Khan, Anzar
Format: Article
Language:English
Subjects:
Biomedical materials
Chemical reactions
click chemistry
Crosslinking
functionalization of polymers
Multifunctional materials
Robustness
sequential reactions
structure
Synthesis
Synthesis (chemistry)
Utilities
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Summary:ABSTRACT Base‐catalyzed reaction between a thiol and an epoxide group is a simple fusion process that leads to the formation of a β‐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. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 3057–3070 Thiol‐epoxy “click” chemistry is increasingly being put to use for the preparation and modification of soft polymeric materials. In this highlight article, different attributes of this reaction—efficiency, regio‐selectivity, speed, robustness, practicality, and sequential reactivity concept—are discussed with the help of literature examples. The emphasis is placed on well‐defined structures. However, selected crosslinked systems and surface modification studies are also included into the discussion.
ISSN:0887-624X
1099-0518
DOI:10.1002/pola.28195