Highly organosoluble metal-free phthalocyanines and metallophthalocyanines: Synthesis and characterization

Bilgin A., Ertem B., Goek Y.

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, no.12, pp.1703-1712, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: Issue: 12
  • Publication Date: 2007
  • Doi Number: 10.1002/ejic.200600943
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1703-1712
  • Keywords: soluble phthalocyanine, phthalonitrile, macrocycles, nickel, zinc, ELECTRICAL-PROPERTIES, COMPLEXES
  • Karadeniz Technical University Affiliated: Yes


The syntheses and characterization of metal-free and metal-containing (Zn and Ni) derivatives of a symmetrically octa-substituted phthalocyanine derived from 4,5:12,13-bis(4'-tert-butylbenzo)-8,9-(4",5"-dicyanobenzo)-6,11-ditosyl- 6,11-diaza-2,15-dithiacyclohexadeca-4,8,12-triene and CuPc from 4,5:12,13-bis(4'-tert-butylbenzo)-8,9-(4",5"-dibromobenzo)-6,11-ditosyl-6,11-diaza-2,15-dithiacyclohexadeca- 4,8,12-triene were carried out. Pentanuclear silver(l) and palladium(II) complexes have also been prepared from nickel(II) phthalocyaninate derivatives. The prepared phthalocyanines were semiconducting materials in the range of 10(-5) to 10(-10) S cm(-1) in vacuo and under atmospheric pressure. The extraction abilities of NiPc and detosylated phthalocyanines were evaluated in chloroform/water by using several heavy-metal picrates such as Ag+, Cd2+, Cu2+, Hg2+, Pb2+, Pd2+, and Zn2+. The extraction affinities of NiPc and detosylated phthalocyanines for Ag+ were found to be the highest in solvent extraction experiments. The new compounds were characterized by using elemental analysis, UV/Vis, FTIR, NMR, MS spectroscopic data and DTA/TG. (C) Wiley-VCH Verlag GmbH & Co.