Novel, soluble, FluXoro functional substituted zinc phthalocyanines; synthesis, characterization and photophysicochemical properties

Three novel phthalonitriles and the respective, peripheral tetrakis zinc phthalocyanines were synthesized and characterized using elemental analysis, IR, 1H NMR, mass spectra and electronic spectroscopy. The phthalocyanines displayed good solubility in organic solvents such as CHCl3, DCM, DMSO, DMF, THF and toluene. The presence of a long chain fluorine substitituent was found to result in reduced aggregation. The singlet oxygen, photodegradation, fluorescence quantum yield, triplet quantum yield and triplet life time of the complexes in toluene were determined. The effect of fluoro-functional groups on the photophysical and photochemical parameters of the zinc(II) phthalocyanines are also reported. Fluorescence quantum yields for the complexes ranged from 0.021 to 0.041