The synthesis of novel unmetallated and metallated phthalocyanines including (E)-4-(3-cinnamoylphenoxy) groups at the peripheral positions and photophysicochemical properties of their zinc phthalocyanine derivatives

• Novel unmetallated and metallated phthalocyanines bearing (E)-4-(3-cinnamoylphenoxy) groups at the peripheral positions.
• The photophysicochemical properties of tetra- and octa-substituted zinc phthalocyanine derivatives.
• The fluorescence quenching behavior of zinc phthalocyanine derivatives by 1,4-benzoquinone.

This paper reports on the synthesis and characterization of new peripherally tetra-substituted metal-free (4), nickel(II) (5), zinc(II) (6), cobalt(II) (7), copper(II) (8), lead(II) (9) and octa-substituted zinc(II) (12) phthalocyanines containing (E)-4-(3-cinnamoylphenoxy) groups for the first time. Synthesized compounds have been characterized by electronic absorption, FT-IR, 1H NMR, 13C NMR, elemental analysis, mass spectra and thermogravimetric analysis. The photophysical (fluorescence quantum yields and lifetimes) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of zinc phthalocyanine derivatives (6 and 12) were investigated in dimethylsulfoxide. The fluorescence quenching behavior of zinc phthalocyanine derivatives (6 and 12) by 1,4-benzoquinone was also examined in same solution.

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