Synthesis and characterization of a triazine containing three phthalocyanines

Ozan N., Bekaroglu O.

POLYHEDRON, vol.22, no.6, pp.819-823, 2003 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 6
  • Publication Date: 2003
  • Doi Number: 10.1016/s0277-5387(03)00003-2
  • Title of Journal : POLYHEDRON
  • Page Numbers: pp.819-823


A new trimeric-s-triazine containing three amino zinc(II) phthalocyanines has been prepared by following the multistep reactions of unsymmetrical substituted phthalocyanines. The zinc(II) phthalocyanine containing an unsymmetrical substituted nitro group was synthesized by means of the well-known statistically mixing method of two different plithalonitriles. 4-Nitrophthalonitrile and 4,5-bis(hexylthio)phthalonitrile were tetramerized in DMF in the presence of zinc acetate at elevated temperature to give a zinc(II) complex, which was then separated by column chromatography on silica gel. The nitro compound was reduced to the amine form by using sodium sulfide as the reducing agent and its ammonium salt was obtained by reaction with gaseous HCl. This compound was then reacted with cyanuric chloride in the presence of potassium carbonate as a base in THF and an interesting trimeric-s-triazine, containing three amino zinc(II) phthalocyanines, was synthesized. The separation of the product was carried out by column chromatography on silica gel. The new compounds were characterized by elemental analysis and UV/VIS, IR, NMR spectra. (C) 2003 Elsevier Science Ltd. All rights reserved.