Novel carbazole containing zinc phthalocyanine photosensitizers: Synthesis, characterization, photophysicochemical properties and in vitro study

Abstract

Tetra and octa substituted novel zinc(II) phthalocyanines (3a and 5a) bearing carbazole groups were synthesized by cyclotetramerization of respective phthalonitrile derivatives (3 and 5). The zinc(II) phthalocyanines (3a and 5a) were converted into the water-soluble quaternized derivatives (3b and 5b) by utilizing dimethylsulphate as quaternizing agent. The synthesized novel compounds were confirmed thruogh FT-IR, UV-vis and MALDI-TOF mass spectroscopic data and elemental analysis as well. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation) properties of new phthalocyanines were determined in dimethylsulfoxide (DMSO). The photophysical and photochemical results were compared according to the number of the carbazole groups on the phthalocyanine core. Additionaly, in vitro photocytotoxicity of the targeted compounds were examined against to hepato cellular carcinoma (HuH-7) cancer cell line for determination of their photosensitizing ability.