Novel organosoluble metal-free and metallophthalocyanines bearing triazole moieties: Microwave assisted synthesis and determination of photophysical and photochemical properties

The synthesis and characterization of new peripherally metal-free (4), nickel (5), zinc (6), cobalt (7), copper (8) and lead (9) phthalocyanines bearing tetra-2-(4-(4-methoxybenzylamino)-5-oxo-3-p-tolyl-4, 5-dihydro-1H-1, 2, 4-triazol-1-yl)ethoxy groups have been described for the first time in this study. These new phthalocyanine compounds have been characterized by several spectral methods such as FT-IR, 1H NMR, 13C NMR, electronic spectroscopy, mass spectra and elemental analyses. The thermal stabilities of these new phthalocyanines were determined by thermogravimetric analysis. The photophysical (fluorescence quantum yields and fluorescence lifetimes) and photochemical (singlet oxygen generations and photodegradation quantum yields) properties of metal-free (4), zinc (6) and lead (9) phthalocyanines were studied in dimethylsulfoxide (DMSO). The fluorescence quenching behavior of metal-free (4), zinc (6) and lead (9) phthalocyanines was also investigated. ► Synthesis and characterization of tetrasubstituted metal-free and metallophthalocyanines. ► Fluorescence behavior of metal-free, zinc(II) and lead (II) phthalocyanines in DMSO. ► High solubility of these novel compounds in several solvents.