Metalloporphyrin polymers bridged with conjugated cyano-substituted stilbene units

A new metalloporphyrin polymer in which the metalloporphyrin units are bridged edge to edge with cyano-substituted stilbene was synthesized from [5,15-bis(4-formylphenyl)-10,20-bis(mesityl) porphyrin] Zn(II) and 1,4-dihexyloxy-2,5-benzenediacetonitrile via the Knoevenagel condensation reaction. The synthesis and characterization of a new porphyrin monomer and polymer are presented. Based on UV-Vis absorption and fluorescence studies, electronic communication between the chromophore groups is low. The relatively high solubility of the materials provides for the preparation of polymer films by spin coating. The polymer film can be doped by FeCl3 and shows limited conductivity. The doped film is extremely stable in air and can be reversibly dedoped by reducing reagents such as NaBH4.