Abstract
A one-step postpolymerization modification that converts three high bandgap poly(arylene ethynylene)s into low bandgap donor–acceptor copolymers is described. The strategy relies on a palladium-catalyzed cyclopentannulation reaction between the main-chain ethynylene functionality and a small molecule aryl bromide (6-bromo-1,2-dimethylaceanthrylene). The reaction installs new cyclopenta[hi]aceanthrylene electron-accepting groups between the electron rich arylenes along the polymer backbone. The modified polymers include poly(9,9-didodecyl-fluorene-2,7-ethynylene), poly(9-dodecyl-carbazole-2,7-ethynylene), and poly(2,5-dioctyloxyphenylene-1,4-ethynylene). The functionalization efficiency was evaluated via isotopic 13C labeling of the polymeric ethynylene carbons and then monitoring the chemical environment of those carbons via NMR spectroscopy. Near complete conversion of the sp carbon species to sp2 carbon species was observed, which demonstrates the high efficiency of the modification strategy. Gel permea...
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