Microwave-assisted synthesis and characterization of phthalocyanines substituted with azo compound containing eugenol moiety


KANTAR C., Mert F., ŞAŞMAZ S.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.696, no.18, pp.3006-3010, 2011 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 696 Issue: 18
  • Publication Date: 2011
  • Doi Number: 10.1016/j.jorganchem.2011.05.014
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.3006-3010
  • Keywords: Phthalocyanine, Microwave, Synthesis, Phthalonitrile, Eugenol, Azo dyes, DERIVATIVES

Abstract

The new metallophthalocyanines (Co, Ni, Cu, and Zn) substituted with azo compound containing eugenol moiety are described. Firstly, azo compound (I) containing eugenol moiety was synthesized by treating eugenol with p-hydroxyaniline. Then phthalonitrile compound (1) was synthesized by microwave-assisted synthesis method. The purification of phthalonitrile compound (1) was carried out by column chromatographic separation. Intramolecular hydrogen bonding in the azo compound (I) prevent base-catalyzed nucleophilic aromatic substitution of OH group belongs eugenol. At the last step, metallophthalocyanines (1a, 1b, 1c, and 1d) were synthesized by the microwave irradiation. The microwave-assisted synthesis method reduces reaction times and enhances the yield of the reactions. All phthalocyanine compounds are soluble in DMF and DMSO. The structures were confirmed by elemental analysis, H-1 NMR, C-13 NMR, UV/Vis, IR and Mass spectra. (C) 2011 Elsevier B. V. All rights reserved.