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

This paper reports on the synthesis and characterization of new peripherally tetra-substituted metal-free (4), nickel(11) (5), zinc(11) (6), cobalt(II) (7), copper(11) (8), lead(II) (9) and eta-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, H-1 NMR, C-13 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. (C) 2013 Published by Elsevier Ltd.