Synthesis, characterization, photophysical and photochemical properties of peripherally tetra-1,2,4-triazol-3-ylthio substituted metal-free phthalocyanine and its zinc(II) and lead(II) derivatives

Phthalonitrile (3) including 4-(4-fluorophenyl)-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thio substituent and its peripherally tetra substituted metal-free (4), zinc(II) (5) and lead(II) (6) phthalocyanine derivatives were prepared and characterized by FTIR, mass, H-1-NMR and C-13-NMR spectroscopic data. All studied phthalocyanines had good solubility in common organic solvents and did not aggregate. The photophysical and photochemical behaviors of the phthalocyanine complexes (4-6) were examined in DMSO to determinate their PDT potential. Singlet oxygen, fluorescence and photodegradation quantum yields showed that zinc(II) phthalocyanine (5) has potential as Type II photosensitizer for PDT applications.

Automated summary

The researchers synthesized and characterized the phthalonitrile and phthalocyanine derivatives, and studied their solubility and photophysical and photochemical behaviors in organic solvents. They found that zinc(II) phthalocyanine has potential as a photosensitizer for photodynamic therapy.