A hybrid polymer of polyaniline and phthalimide dyes

A novel polyaniline derivative containing an emissive chromophore in its backbone was prepared by a palladium-catalyzed aryl amination. The incorporation of a 3,6-diamino phthalimide dye imparts a red color to the leucoemeraldine base analogues while reducing the overall electron density in the chain. The incorporated dye acts as a colorimetric tag indicative of the oxidation state of the polyaniline analogue. The three different oxidation states of the polymers were unambiguously characterized by comparison with an oligomeric model compound using IR and UV–vis spectroscopy. The emeraldine analogue of the polymer shows a measured conductivity of 10−5 S cm−1 and unlike polyaniline, this material exhibits yellow fluorescence in solution. A cyclic tetramer was also isolated from the reaction mixture and 2D-WAXS measurements on an extruded fiber reveal that it forms a hexagonal columnar packing.