Microwave-assisted synthesis, characterization and aggregation properties of phthalocyanines containing azo dye

Abstract

The new zinc phthalocyanines substituted with azo compound are described. Firstly, azo compound (I) was synthesized by treating phenol with 4-iodoaniline. Then phthalonitrile compounds (1, 2 and 3) were synthesized by nucleophilic aromatic substitution. At the last step, novel zinc phthalocyanines (1a, 2a and 3a) were synthesized by the microwave irradiation. The microwave-assisted synthesis method reduces reaction times and enhances the yield of the reactions. All phthalocyanine compounds are soluble in DMF and DMSO. The structures were confirmed by elemental analysis, 1H NMR, 13C NMR, UV/visible, IR and mass spectra. Aggregation properties of phthalocyanines were investigated at different concentrations in DMSO (for 1a) and CHCl3 (for 2a and 3a).