The synthesis, characterization, electrochemical and spectroelectrochemical properties of a novel, cationic, water-soluble Zn phthalocyanine with extended conjugation

A novel Zn phthalocyanine substituted with four dimethylaminocinnamaldiminophenyloxy substituents at peripheral positions was obtained by the condensation of various 4′-aminophenoxy substituted phthalocyanines and 4-(dimethylamino)cinnamaldehyde. Quaternization of the dimethylamino functionality produced cationic Zn phthalocyanines which were soluble in both water and other polar solvents such as methanol and DMSO. The novel compounds were characterized using elemental analysis, IR, 1H NMR, UV–Vis and MALDI-TOF MS spectral data. Electrochemical, in situ spectroelectrochemical, and in situ electrocolorimetric measurements revealed that the complexes undergo electron transfer reactions via the nitro and amine groups in addition to common Pc ring-based processes.