Synthesis, structural and spectroscopic characterization, and photophysical and photochemical properties of peripherally tetratriazole-subsituted highly soluble metallophthalocyanines

The synthesis of novel zinc (II) (4), nickel (II) (5), cobalt (II) (6) and copper (II) (7) phthalocyanines substituted with four [1,2,4]triazole groups on peripheral positions are described for the first time in this study. All the new compounds are characterized by a combination of elemental analyses, IR, 1H and 13C NMR, mass and UV–Vis spectroscopy techniques. Aggregation behaviors of all these novel compounds were investigated and they showed monomeric behavior in DMSO between 2 × 10−6 and 1.2 × 10−5 M concentrations. The photophysical (fluorescence quantum yield and lifetime) and photochemical (singlet oxygen generation and photodegradation quantum yield) properties of the zinc phthalocyanine derivative (4) were studied in dimethylsulfoxide (DMSO). The fluorescence quenching behavior of the zinc phthalocyanine derivative (4) was also investigated. The fluorescence emission of this phthalocyanine derivative is effectively quenched by 1,4-benzoquinone in DMSO. The other synthesized phthalocyanine complexes (8, 9 and 10) were not appropriate for photophysical and photochemical studies due to the paramagnetic behavior of the central metals in the phthalocyanine cavity of these complexes.

Metallophthalocyanines (Zn, Ni, Co and Cu) substituted with four [1,2,4]triazole groups on peripheral positions have been successfully synthesized and characterized. The aggregation behaviors of these novel complexes have been investigated. Photophysical and photochemical properties of the zinc phthalocyanine have also been investigated.Figure optionsDownload as PowerPoint slide