The new ball-type zinc phthalocyanine with S-S bridge; Synthesis, computational and photophysicochemical properties

In this study, the starting compound 4,4'-disulfanediyldiphthalonitrile (1) and its ball-type zinc phthalocyanine (2) were synthesized and characterized by standard spectroscopic methods. The molecular structure and supramolecular dynamics of the compound (1) have been investigated by the analysis of the single crystal X-ray diffraction data. To further understand the intermolecular interactions of compound (1), the Hirshfeld surface analysis has been carried out. The compound (1) and (2) were investigated by quantum chemical calculations. Their quantum chemical parameters such as highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), chemical hardness were performed by B3lyp, HF, M062x method. The Delta G values of the compound (1) and (2) were calculated by using the obtained results. The calculated Infrared spectroscopy, Nuclear Magnetic Resonance, and UV-vis spectra of the compounds were investigated. In addition, photophysical (fluorescence quantum yields) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of newly synthesized ball-type zinc phthalocyanine (2) were investigated in dimethyl sulfoxide (DMSO) solutions. We obtained very high singlet oxygen quantum yields as 0.89, suggesting its potential as photosensitizer in PDT treatment.