Photophysical and Photochemical Properties of Fluorinated and Nonfluorinated n-Propanol-Substituted Zinc Phthalocyanines

Abstract

The synthesis of symmetrical fluorinated and nonfluorinated zinc(II) phthalocyanine derivatives obtained from 4,5-diclorophthalonitrile, 4-nitrophthalonitrile and 3-nitrophthalonitrile substituted with 2,2,3,3-tetrafluoro-1-propanol and n-propanol are described. The comparison of the photophysicochemical properties of fluorinated and nonfluorinated substituted zinc(II) phthalocyanines is reported for the first time. The new compounds have been characterized by elemental analysis, IR, H-1 NMR and F-19 NMR spectroscopy, electronic spectroscopy and mass spectra. The photophysical and photochemical properties of the compounds were studied in dimethyl sulfoxide (DMSO). The complexes were quenched with benzoquinone (BQ), and their fluorescence-quenching properties were investigated in the same solvent. The effects of the number of the substitution and the position on the photophysical and photochemical parameters of the zinc(II) phthalocyanines 1a-7a are also reported. Photophysical and photochemical properties of phthalocyanine complexes are very useful for photodynamic therapy (PDT) of cancer applications. In particular, high singlet-oxygen quantum yields are very important for Type II mechanisms. These complexes have good singlet-oxygen quantum yields and show potential as Type-II photosensitizers.