Novel metal-free, metallophthalocyanines and their quaternized derivatives: Synthesis, spectroscopic characterization and catalytic activity of cobalt phthalocyanine in 4-nitrophenol oxidation


ACAR İ., BAYRAK R., SAKA E. T. , BIYIKLIOĞLU Z., KANTEKİN H.

POLYHEDRON, vol.50, no.1, pp.345-353, 2013 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 50 Issue: 1
  • Publication Date: 2013
  • Doi Number: 10.1016/j.poly.2012.11.032
  • Journal Name: POLYHEDRON
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.345-353
  • Keywords: Phthalocyanine, Schiff base, Cationic, Cobalt, Catalyst, Oxidation, SUBSTITUTED ZINC PHTHALOCYANINES, METHANOL-WATER MIXTURE, PHOTODYNAMIC THERAPY, MICROWAVE IRRADIATION, PHOTOCHEMICAL PROPERTIES, SOLUBLE PHTHALOCYANINES, AGGREGATION PROPERTIES, ELECTROCHEMISTRY, PHOTOSENSITIZERS, CANCER

Abstract

Novel metal-free, Zn and Co phthalocyanines substituted with four 4-[4-((E)-{[4-(dimethylamino)phenyl]imino}methyl)phenoxy] substituents at peripheral positions have been synthesized. Quaternization of the dimethylamino functionality produced quaternized cationic metal-free, Zn and Co phthalocyanines which were soluble in DMF, DMSO and pyridine. The aggregation behavior of these compounds was investigated in different concentrations of chloroform for the metal-free, Zn and Co phthalocyanines, and DMF for the quaternized metal-free, Zn and Co phthalocyanines. The effect of solvents on the absorption spectra was studied in various organic solvents. Cobalt phthalocyanine complex 6 was tested as a catalyst for the oxidation of 4-nitrophenol with different oxidants, such as tert-butylhydroperoxide (TBHP), m-chloroperoxybenzoic acid (m-CPBA) and hydrogen peroxide (H2O2), in organic solvent. The novel compounds were characterized using IR, H-1 NMR, C-13 NMR, UV-Vis, MS spectral data and elemental analysis. (C) 2012 Elsevier Ltd. All rights reserved.