The Use of Piers–Rubinsztajn Conditions for the Placement of Triarylamines Pendant to Silicone Polymers

Abstract

The use of Piers–Rubinsztajn conditions was explored for the synthesis of silicone polymers bearing pendant triarylamine functionality. We have found that up to 60% of the hydride groups of a silicone copolymer can be successfully substituted with a triarylamine moiety, without metathesis or redistribution of the silicone. The resulting polymers are hydrolytically stable. The functionalization procedure is straightforward, conducted under ambient conditions with a simple one-step work-up, and avoids the use of a metal-based catalyst. The resulting phenylated triarylamine–silicone hybrid polymer was characterized by optical absorption and fluorescence spectroscopy, CV, and differential scanning calorimetry. The hybrids maintain the physical appearance of a silicone polymer while adopting the photophysical and electrochemical characteristics of the triarylamine.