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

Serxho Selmani; Luke Vanderzwet; Andrew J. Kukor; Derek J. Schipper

doi:10.1055/s-0037-1610837

Synlett, Table of Contents

Synlett 2018; 29(19): 2552-2556
DOI: 10.1055/s-0037-1610837

cluster

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

Serxho Selmani §

,

Luke Vanderzwet §

,

Andrew J. Kukor

,

Derek J. Schipper *

Department of Chemistry, Waterloo Institute for Nanotechnology, University of Waterloo, 200 University Ave. W., Waterloo, Ontario, N2L 3G1, Canada Email: derek.schipper@uwaterloo.ca

› Author Affiliations

Abstract

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^§ These authors contributed equally to this work.

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 M_n values ranging from 8 to 23 kDa without producing stoichiometric amounts of waste.

Key words

hydroarylation - polymer synthesis - materials - heteroaromatics - rhodium catalysis

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References

References and Notes

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