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Thiol–Ene Click Chemistry

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  • This manuscript is dedicated to Charles Hoyle, who passed away on September 7, 2009, while working on revisions to this manuscript. His work on thiol–ene chemistry and his passion and enthusiasm for that chemistry was legendary. He was a dedicated husband, father, and advisor, and a brilliant scientist who is missed by all who knew him.

Abstract

Following Sharpless′ visionary characterization of several idealized reactions as click reactions, the materials science and synthetic chemistry communities have pursued numerous routes toward the identification and implementation of these click reactions. Herein, we review the radical-mediated thiol–ene reaction as one such click reaction. This reaction has all the desirable features of a click reaction, being highly efficient, simple to execute with no side products and proceeding rapidly to high yield. Further, the thiol–ene reaction is most frequently photoinitiated, particularly for photopolymerizations resulting in highly uniform polymer networks, promoting unique capabilities related to spatial and temporal control of the click reaction. The reaction mechanism and its implementation in various synthetic methodologies, biofunctionalization, surface and polymer modification, and polymerization are all reviewed.

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