Recently, direct arylation has emerged as a novel methodology that is on the verge of large-scale application. By eliminating pre-functionalization of one of the coupling partners, direct arylation offers a �greener� route to installing carbon-carbon bonds, and it is being actively investigated by medicinal chemists. However, despite the benefits in terms of atom economy and minimal organometallic waste, direct arylation has not been incorporated into the standard toolkit for constructing organic electronic materials. To address this deficiency, we studied small-molecule model systems to develop palladium-catalyzed direct arylation polymerization conditions, which were then applied to the synthesis of regioregular poly(3-hexylthiophene). Polymerization conditions were optimized by monitoring both molecular weight and regioregularity using gel permeation chromatography and NMR spectroscopy, respectively. Ongoing research regarding the substrate scope for palladium-catalyzed direct arylation polymerizations will also be presented.

Synthesizing organic electronic materials by palladium-catalyzed direct arylation polymerization

243rd National Meeting (2012)

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