Synthesis, investigation of photophysical and photochemical properties of metal free and metallophthalocyanines that have triazole groups on peripheral environment

Substituted hydrazine (7) was synthesized from the reaction between Ethyl 2-(4-chlorophenyl)acetimidate hydrochloride and 4-chlorobenzhydrazite in absolute ethanol, substituted triazole (8) was synthesized from the reaction between compound (7) and hydrazine hydrate in n-propanol. The Schiff base derivative (9) was obtained from the reaction between compound (8) and 4-hydroxybenazldehyde in glacial acetic acid. The substituted phthalonitriles (1) and (10) were synthesized by the reactions between 4-nitrophthalonitrile and 4-(3,4-dimethoxyphenylethyl)-3-methyl-1H-1,2,4-triazole-5(4H)-on and (E) -4- ((3-( 4-chlorobenzyl )-5 - ( 4-chlorophenyl)-3H-1,2,4-triazole-4(5H)-ylimino) methyl)phenol (9), respectively in dry DMF and in the presence of dry potassium carbonate. Metal free phthalocyanines (2) and (11) were obtained from these phthalonitriles (1) and (10) in n-hexanol at reflux temperature. While the preparation of the metallophthalocyanines (3-6) were achieved from the phthalonitrile (1) by microwave irradiation, the classical method was used for the synthesis of metallophthalocyanines (12-15) from the phthalonitrile (10). The aggregation behaviours of these novel phthalocyanines and the photophysical and photochemical properties of the zinc(II) phthalocyanines (3) and (12) have been investigated.