Synthesis and characterization of novel flavonoid-substituted phthalocyanines using (±)naringenin

In this study, novel unsymmetrical mono- and di-substituted metal free and metallo phthalocyanines containing peripheral naringeninoxy moieties have been prepared. The naringenin-substituted phthalonitrile was synthesized from 4-nitrophthalonitrile and (±)naringenin in dimethylsulfoxide. Preparation of unsymmetrical mono- and di-substituted phthalocyanines, 2-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatozinc, 2,9-bis-naringenin-7-O-phthalocyaninatocobalt and 2,9-bis-naringenin-7-O-phthalocyanine was performed at 120–140 °C using the corresponding phthalonitrile in the presence of N,N-dimethylethanolamine (DMAE), ZnCl2, CoCl2 and LiCl, respectively. Synthesized new phthalocyanine compounds have been characterized by elemental analysis and 1H NMR, 13C NMR, FT-IR, MS and UV–vis spectroscopy. These are the first known examples of flavonoid-substituted phthalocyanines.