Novel phthalocyanines bearing 7-oxy-3-(3,5-difluorophenyl)coumarin moieties: Synthesis, characterization, photophysical and photochemical properties

• New peripheral and nonperipheral 7-oxy-3-(3,5-difluorophenyl) coumarin substituted zinc (II) and indium (III) phthalocyanines.
• Photophysical and photochemical properties in DMF.
• Ground state electronic absorption and fluorescence spectra.
• Photodynamic therapy.

Two novel phthalonitriles,7-(2,3-dicyanophenoxy)-3-(3,5-difluorophenyl) coumarin (2), 7-(3,4-dicyanophenoxy)-3-(3,5-difluorophenyl) coumarin (3), and corresponding zinc(II)-, indium(III) phthalocyanines were prepared. Additionally, photophysical (fluorescence quantum yields and lifetimes), photochemical (singlet oxygen generation and photodegradation under light irradiation) and spectral properties of the resulting peripherally/non-peripherally tetra 7-oxy-3-(3,5-difluorophenyl) coumarin substituted zinc (II) and indium (III) phthalocyanines (4–7) were investigated. All compounds (1–7) were characterized by elemental analysis, IR, 1H NMR, mass and UV–vis spectral data. The obtained 7-oxy-3-(3,5-difluorophenyl) coumarin bearing pure zinc (II) and indium (III) phthalocyanine complexes were well soluble in organic solvents and displayed good singlet-oxygen generation and appropriate photodegradation.

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