Synthesis of Poly(heteroarylenevinylene) Derivatives via Rhodium-Catalyzed Hydroarylation of Alkynes

Abstract

Organic electronics has developed into a significant field of research and industry in the last decade. The progress has been enabled by the many advancements made in synthetic technologies, which allow for the design of a plethora of interesting material candidates. Poly(p-phenylenevinylene) derivatives (PPVs) are a particularly interesting class of polymers that were among the first to garner attention. However, due to their demanding syntheses, limited scope, and relative intolerance to heterocycles, PPVs have fallen out of popularity. New synthetic methods, such as direct C–H bond activation, have emerged that allow for the creation of polyheteroaromatics through the use of simpler starting materials than those used in traditional cross-coupling strategies. Here, we report an extension of a hydroarylation reaction to the synthesis of poly(heteroarylenevinylene) derivatives (PHAVs) containing various desirable heterocycles with Mn values ranging from 8 to 23 kDa without producing stoichiometric amounts of waste.