The new zinc phthalocyanine having high singlet oxygen quantum yield substituted with new benzenesulfonamide derivative groups containing schiff base

• Published in: Journal of molecular structure 2020-02, Vol.1202, p.127181, Article 127181
• Main Authors: Pişkin, Mehmet, Canpolat, Erdal, Öztürk, Ömer Faruk
• Format: Article
• Language: English
• Subjects: photochemical; photophysical; phthalocyanine; sulfa drugs
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2019.127181

The new (E)-4-((5-bromo-2-hydroxy-3-methoxybenzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 1, (E)-4-((5-bromo-2-(3,4-dicyanophenoxy)-3-methoxy benzylidene)amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide 2 and peripheral tetrakis-(E)-4-((5-bromo-3-methoxy-2-(λ1-oxidaneyl)benzylidene) amino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide substituted zinc(II) phthalocyanine 3 were been synthesized and characterized using UV–vis, FT-IR, 1H NMR, 13C NMR (except for 3), MALDI-TOF mass spectra and elemental analysis for the first time. The spectroscopic, photophysical and photochemical properties for the phthalocyanine 3 were been described in dimethyl sulfoxide. These properties of the phthalocyanine 3 as a photosensitizer are very useful for photodynamic therapy application and its good fluorescence properties, high singlet oxygen quantum yield and appropriate photodegradation quantum yield are very important for Type II mechanisms. It has the remarkable potential to be used as Type II photosensitizers for the treatment of cancer in photodynamic therapy with these features. •The new benzenesulfonamide compound containing Schiff base and thiadiazole derivatives, its phthalonitrile derivative as well as its zinc(II) phthalocyanine were synthesized and characterized.•Photophysical and photochemical properties of the zinc(II) phthalocyanine were reported in dimethylsulfoxide.•It has good fluorescence properties, high singlet oxygen quantum yield and appropriate photodegradation quantum yield.•It has considerable potential to be used as Type II photosensitizers for cancer treatment in photodynamic therapy.