Peripherally, non-peripherally and axially pyrazoline-fused phthalocyanines: synthesis, aggregation behaviour, fluorescence, singlet oxygen generation, and photodegradation studies

Abstract

In this study, the synthesis of phthalocyanine compounds, which are known as second-generation photosensitizing agents in photodynamic therapy and play an important role in the treatment of cancer, is presented. Pyrazoline-fused axial silicon phthalocyanine (HY-SiPc), peripheral zinc phthalocyanine (HY-ZnPcp), and non-peripheral zinc phthalocyanine (HY-ZnPcnp) were synthesized and characterized by common spectroscopic methods (NMR, FT-IR, UV-Vis spectroscopies, and mass spectrometry). In order to determine the photophysical and photochemical properties, the solvent effect in different organic solvents (THF, DMSO, CHCl3, DMF, and EtOAc) was studied, and DMSO was chosen as a suitable solvent for further studies. According to the results, the pyrazoline-fused peripheral zinc phthalocyanine (HY-ZnPcp) showed the highest singlet oxygen production, and it is thought to be a photosensitizer candidate for photodynamic therapy.