Darstellung und Untersuchung der photochemischen und photosensibilisierenden Eigenschaften verschieden substituierter Zn(II)-Phthalocyanine

Abstract

Different zinc(II) phthalocyanines containing o-carboranyl- or dodecahydrododecaborate substituents and zinc(II) phthalocyanines containing electron-donating or withdrawing substituents were prepared. These new tetrasubstituted boronated phthalocyanines were tested for their photocatalytic activities in the photooxidation of citronellol. The singulet oxygen quantum yields of boronated phthalocyanines were measured by using DPBF as chemical quencher. It was seen that o-carboranyl substituted phthalocyanines have higher photocatalytic activities than their not boronated analogues. The investigation of phototoxic properties of boronated phthalocyanines has been carried out on V79 cell. The following properties of the phthalocyanines containing electron-donating or withdrawing substituents were investigated: singlet oxygen quantum yields, photo-oxidative stabilities and photocatalytic activities (photooxidation of (S)-(-)-citronellol). In addition, positions of HOMO/LUMO energy levels of ground states (S0), first excited singlet states (S1) and first excited triplet states (T1) were calculated. Correlations between properties of the investigated compounds were found: relation between HOMO energy levels of S0 and photo-decompositions, photocatalytic activities and photo-decompositions. Singlet oxygen quantum yields are around 0.55 and independent from calculated triplet energies.