Design and Synthesis of New Conjugated Porphyrin Copolymers for Optical-Electronic Applications

New linear conjugated porphyrin polymers were synthesized by a palladium-catalyzed cross-coupling reaction of [5,15-bis(ethynyl)-10,20-bis (mesityl)porphyrin]zinc and diiodobenzene derivatives. Enhanced solubility of the conjugated porphyrin polymers was achieved by attachment of long alkyl ether or dialkyl amide groups to the aryl moiety, resulting in unambiguous characterization by 1H NMRLR, GPC, UV-Vis and fluorescence spectroscopies. The introduction of alkyl ether (electron donor) or dialkyl amide (electron acceptor) results in significant modulation of the electronic properties of the conjugated porphyrin polymers due to strong electronic coupling. The spectroscopic and electronic characterization of these materials provides for comparison to earlier preparations of ethynyl bridged conjugated copolymers in which electronic coupling was substantially weaker.