Peripheral and non-peripheral long-chain tetrasubstituted phthalocyanines: Synthesis, spectroscopic characterization and aggregation properties

New 6-(quinolin-6-yloxy)hexan-1-ol 3 and phthalonitrile derivatives 4 and 5 bearing 6-(quinolin-6-yloxy)hexan-1-ol substituent at peripheral and non-peripheral positions have been synthesized. Novel peripheral and non-peripheral zinc 4a, 5a and cobalt 4b, 5b phthalocyanines were synthesized and characterized for the first time. The synthesis of metallophthalocyanines 4a, 4b, 5a, 5b derived from 4-{[6-(quinolin-6-yloxy)hexyl]oxy}phthalonitrile 4 and 3-{[6-(quinolin-6-yloxy)hexyl]oxy}phthalonitrile 5 were carried out by microwave irradiation. Aggregation properties of metallophthalocyanines were investigated at different concentrations in chloroform, tetrahydrofuran and dimethylsulfoxide. The new compounds have been characterized by using UV–vis, IR, 1H NMR, 13C NMR and MS spectroscopic data.

► Synthesis and characterization of peripheral tetrasubstituted metallophthalocyanines.
► Synthesis and characterization of non-peripheral tetrasubstituted metallophthalocyanines.
► Investigation of aggregation properties of metallophthalocyanines in different solvents.