Synthesis, photophysical and photochemical properties of highly soluble phthalocyanines substituted with four 3,5-dimethylpyrazole-1-methoxy groups

The synthesis and characterization of new peripherally tetra-3,5-dimethylpyrazole-1-methoxy substituted metal-free (4), zinc (5), nickel (6), cobalt (7), copper (8) and lead (9) phthalocyanines are described for the first time in this study. The photophysical (fluorescence quantum yields and fluorescence lifetimes) and photochemical (photodegradation and singlet oxygen quantum yields) properties of metal-free (4), zinc (5) and lead (9) phthalocyanines are studied in dimethylsulfoxide (DMSO). Nickel (6), cobalt (7) and copper (8) phthalocyanines (6–8) did not evaluate for this purpose due to transition metal and paramagnetic behavior of central metals in the phthalocyanine cavity. The fluorescence quenching behavior of metal-free (4), zinc (5) and lead (9) phthalocyanines are also investigated. The fluorescence emissions of these phthalocyanines are effectively quenched by 1,4-benzoquinone in DMSO.

In this work was shown that syntheses and characterization of 3,5-dimethylpyrazole-1-methoxy substituted metal-free, zinc, nickel, cobalt, copper and lead phthalocyanines. The photophysical (fluorescence quantum yield and lifetime), photochemical (singlet oxygen generation and photodegradation quantum yield) and fluorescence quenching properties of novel metal-free, zinc and lead phthalocyanines have been investigated in DMSO.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of metal-free, zinc, nickel, cobalt, copper and lead phthalocyanines.
► Tetra-(3,5-dimethylpyrazole-1-methoxy) substituted phthalocyanines.
► Photophysical and photochemical properties in DMSO.
► The effect of the central metals on the photophysical and photochemical properties.