Highly soluble 3,4-(dimethoxyphenylthio) substituted phthalocyanines: Synthesis, photophysical and photochemical studies

The synthesis of a new 3,4-(dimethoxyphenylthio) substituted phthalonitrile (1) and its soluble metal free (2), zinc (II) (3), oxo-titanium (IV) (4) and nickel (II) (5) phthalocyanine derivatives are reported for the first time. The new compounds have been characterized by elemental analysis, FT-IR, 1H NMR, UV–Vis, fluorescence spectroscopies and mass spectra. General trends are described for fluorescence, photodegradation and singlet oxygen quantum yields and fluorescence lifetimes of oxo-titanium (IV) and zinc (II) phthalocyanine compounds in dimethylsulfoxide (DMSO). The effects of the metal ion on the photophysical and photochemical parameters for these phthalocyanines (3 and 4) are also reported.

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► New metal-free (2) and metallophthalocyanines (3–5) were synthesized.
► These new phthalocyanine derivatives show the enhanced solubility in organic solvents.
► The photophysical and photochemical properties of zinc (II) and TiO (IV) phthalocyanine (3 and 4) are investigated in DMSO.
► Ground state electronic absorption and fluorescence spectra.
► Potential for photodynamic therapy.