New soluble methylendioxy-phenoxy-substituted zinc phthalocyanine derivatives: Synthesis, photophysical and photochemical studies


Erdogmus A. , Nyokong T.

POLYHEDRON, vol.28, no.14, pp.2855-2862, 2009 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 28 Issue: 14
  • Publication Date: 2009
  • Doi Number: 10.1016/j.poly.2009.06.019
  • Title of Journal : POLYHEDRON
  • Page Numbers: pp.2855-2862
  • Keywords: Zinc phthalocyanines, Triplet quantum yield, Fluorescence quantum yield, Singlet oxygen, Photodynamic therapy, OXYGEN QUANTUM YIELDS, METAL-ION BINDING, PHOTODYNAMIC THERAPY, SINGLET OXYGEN, FLUORESCENCE, METALLOPHTHALOCYANINES, ELECTROCHEMISTRY, COMPLEXES, PHOTOSENSITIZERS, CANCER

Abstract

The syntheses of new three phthalonitriles (1, 2 and 3), together with photophysical and photochemical properties of the resulting peripherally and non-peripherally tetrakis- and octakis 3,4-(methylendioxy)-phenoxy-substituted zinc phthalocyanines (4, 5 and 6) are described for the first time. Complexes 4, 5 and 6 have been synthesized and characterized by elemental analysis, IR, H-1 NMR spectroscopy, electronic spectroscopy and mass spectra. Complexes 4, 5 and 6 have good solubility in organic solvents such as CHCl3, DCM, DMSO, DMF, THF and toluene and are mainly not aggregated (except for complex 6 in DMSO) within a wide concentration range. General trends are described for singlet oxygen, photodegradation, fluorescence quantum yields, triplet quantum yields and triplet life times of these complexes in DMSO and toluene. Complex 4 has higher singlet oxygen quantum yields, fluorescence quantum yields, triplet quantum yields and triplet life times than complexes 5 and 6. The effect of the solvents on the photophysical and photochemical parameters of the zinc(II) phthalocyanines (4, 5 and 6) are also reported. (C) 2009 Elsevier Ltd. All rights reserved.