Synthesis, characterization and electrochemistry of a new organosoluble metal-free and metallophthalocyanines

Biyikhoglu Z., GUNER E. T., Topcu S., KANTEKİN H.

POLYHEDRON, vol.27, no.6, pp.1707-1713, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 6
  • Publication Date: 2008
  • Doi Number: 10.1016/j.poly.2008.02.004
  • Journal Name: POLYHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1707-1713
  • Keywords: phthalocyanines, dinitrile, metallophthalocyanines, cyclic voltammetry, MICROWAVE-ASSISTED SYNTHESIS, PHTHALOCYANINES, COMPLEXES, LIGANDS
  • Karadeniz Technical University Affiliated: Yes

Abstract

4 -[2-(Phenylthio)ethoxy]phthalonitrile 3 was synthesized by nucleophilic displacement of nitro group in 4-nitrophthalonitrile with 2-(phenylthio)ethanol 1. The metal-free phthalocyanine 4 was prepared by the reaction of a dinitrile monomer with 2-(dimethylamino)ethanol. Ni(II), Co(II), Cu(I) phthalocyanines 5, 7, 8 were prepared by reaction of the dinitrile compound with the chlorides of Ni(II), Co(II), Cu(I) in DMAE. Zn(II) phthalocyanine 6, was prepared by reaction of the dinitrile compound with the acetates of Zn(II) in DMAE. Electrochemical behaviours of novel metal-free, Co(II) and Zn(II) phthalocyanines were investigated by cyclic voltammetry, potential differential pulse voltammetry techniques. The new compounds were characterized by a combination of IR, H-1 NMR, C-13 NMR, UV-Vis, elemental analysis and MS spectral data. (C) 2008 Elsevier Ltd. All rights reserved.