Palladium-catalyzed direct arylation polymerization (DARP) has emerged as a viable method for the synthesis of organic electronic materials. By circumventing organometallic coupling partners, direct arylation minimizes both the required synthetic steps and the hazardous waste produced. Unfortunately, polymers generated using DARP can suffer from lower regioregularity and significant crosslinking, presumably via unselective C-H activation. To address this limitation, we investigated small-molecule model systems to develop improved DARP conditions, which were then applied to the synthesis of conjugated polymers. Small-molecule studies were conducted using GCMS analysis, while polymers were thoroughly characterized using a combination of gel permeation chromatography, NMR and UV-vis spectroscopy, grazing incidence x-ray diffraction, differential scanning calorimetry, and thermal gravimetric analysis. Ongoing research regarding the substrate scope for DARP will also be presented.

Enhancing the regioselectivity of C-H activation in palladium-catalyzed direct arylation polymerization (DARP)

245th National Meeting (2013)

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