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

Abstract

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, ¹H-NMR and ¹³C-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.

Graphical Abstract

Keywords:

• Triazole
• phthalocyanine
• singlet oxygen
• fluorescence quenching
• photosensitizer

Disclosure statement

No potential conflict of interest was reported by the authors.