Spectroscopic and photophysicochemical properties of zinc(II) phthalocyanine substituted with benzenesulfonamide units containing schiff base

Abstract

In this study, compounds (E)-4-((5-bromo-2-hydroxy-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesul-fonamide 1, (E)-4-((5-bromo-2-(3,4-dicyanophenoxy)-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide 2 and, complex 2(3),9(10),16(17),23(24)-tetra-[(E)-4-((5-bromo-3-methoxy-2-(λ1-oxidanyl)benzylidene)amino)-N-(pyridine-2-yl)benzenesulfonamide]phthalocyaninato zinc(II) 3 were synthesized for the first time. Their structures (1 –3) were characterized by spectroscopic methods such as FTIR, 1H NMR,13C NMR, UV–vis, MALDI-TOF mass spectra and elemental analysis. The spectroscopic, aggregation, photophysical and photochemical properties of zinc(II) phthalocyanine 3 in dimethyl sulfoxide were investigated and the effects on the above-mentioned properties were reported as a result of the presence of benzenesulfonamide derivatives containing different bioactive groups, in their peripheral positions. In addition, its above-mentioned properties were also reported by comparing different species with those of their substituted and/or unsubstituted counterparts. The zinc(II) phthalocyanine 3 can be a potential photosensitizer candidate in photodynamic therapy, which is an effective alternative therapy in cancer treatment, due to its good solubility in commonly known solvents and monomeric species, as well as its adequate and favorable fluorescence, singlet oxygen production and photostability.