Novel water-soluble metal-free and metallophthalocyanines: Synthesis, spectroscopic characterization and aggregation properties

In this study, the preparation of novel metal-free phthalocyanine 2, metallophthalocyanine complexes 3, 4, 5, 6 (MPcs, M = Ni, Co, Cu, Fe) with 6-oxyquinoline functional group and quaternized metallophthalocyanine derivatives 3a, 4a, 6a (MPcs, M = Ni, Co, Fe), was achieved. The reaction of 4-(quinolin-6-yloxy)phthalonitrile 1 in 2-(dimethylamino)ethanol as the solvent, the metal-free phthalocyanine 2 was synthesized. The synthesis of metallophthalocyanines 3-6 derived from 4-(quinolin-6-yloxy)phthalonitrile 1 were carried out by microwave irradiation. Aggregation properties of Pcs were investigated at different concentrations in chloroform, dimethylsulfoxide, dimethylformamide and water. The metal-free phthalocyanine 2 showed the aggregation in polar solvent DMSO, whereas in chloroform no aggregation was observed. The effect of the concentration on the aggregation properties of complexes 2, 3, 4 and 5 were studied in chloroform. No aggregation was demonstrated in chloroform from concentration between 1 × 10−5 and 0.4 × 10−5 M. The new compounds have been characterized by using elemental analysis, UV-Vis, IR, 1H NMR, 13C NMR and MS spectroscopic data.