Visible-Light-Initiated Thiol-Michael Addition Polymerizations with Coumarin-Based Photobase Generators: Another Photoclick Reaction Strategy

ACS Macro Lett. 2016 Feb 16;5(2):229-233. doi: 10.1021/acsmacrolett.5b00923. Epub 2016 Jan 22.

Abstract

An efficient visible-light-sensitive photobase generator for thiol-Michael addition reactions was synthesized and evaluated. This highly reactive catalyst was designed by protecting a strong base (tetramethyl guanidine, TMG) with a visible-light-responsive group which was a coumarin derivative. The coumarin-coupled TMG was shown to exhibit extraordinary catalytic activity toward initiation of the thiol-Michael reaction, including thiol-Michael addition-based polymerization, upon visible-light irradiation, leading to a stoichiometric reaction of both thiol and vinyl functional groups. Owing to its features, this visible-light photobase generator enables homogeneous network formation in thiol-Michael polymerizations and also has the potential to be exploited in other visible-light-induced, base-catalyzed thiol-click processes such as thiol-isocynate and thiol-epoxy network-forming reactions.