Synlett 2018; 29(19): 2552-2556
DOI: 10.1055/s-0037-1610837
cluster
© Georg Thieme Verlag Stuttgart · New York

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

Serxho Selmani §
,
Luke Vanderzwet §
,
Andrew J. Kukor
,
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
We thank NSERC, the University of Waterloo, and the Canada Foundation for Innovation and the Canada Research Chairs Program (CRC-Tier II, D.J.S.) for financial support. S.S. thanks the Government of Ontario for an Ontario Graduate Scholarship. L.V. thanks NSERC for a postgraduate scholarship. A.J.K thanks NSERC for an undergraduate research student award.
Further Information

Publication History

Received: 03 October 2018

Accepted after revision: 29 October 2018

Publication Date:
12 November 2018 (online)

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

Supporting Information

 
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