The synthesis and characterization of functionalized polyfluorinated phthalocyanines

Ozcecmeci M., Hamuryudan E.

DYES AND PIGMENTS, vol.77, no.2, pp.457-461, 2008 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 77 Issue: 2
  • Publication Date: 2008
  • Doi Number: 10.1016/j.dyepig.2007.07.013
  • Journal Name: DYES AND PIGMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.457-461
  • Keywords: metallophthalocyanines, regioselective nucleophilic aromatic substituents, hexylthio, REGIOSELECTIVE SYNTHESIS, MONO-(PENTAFLUOROPHENYL)PORPHYRINS, PORPHYRINS
  • Istanbul Technical University Affiliated: Yes

Abstract

4-(2',3',4',5',6'-Pentafluorobenzyloxy)phthalonitrile was employed with hexanethiol to prepare 4-(2',3',5',6'-tetrafluoro-4'-hexylthio-benzyloxy)phthalonitrile, by the selective displacement of the para-fluorine atom using K2CO3 in DMF. The new Zn(II), Ni(II) and Co(II) phthalocyanines with four, peripheral fluoro-hexylthiobenzyloxy groups were synthesized from 4-(2',3',5',6'-tetrafluoro-4'-hexylthio-benzyloxy)phthalonitiile and the corresponding divalent metal salt (Zn(CH3COO)(2), NiCl2 or COCl2). The blue-green phthalocyanines were soluble in common organic solvents. The structures of the target compounds were confirmed using elemental analysis, UV-vis, FT-IR, H-1 NMR, F-19 NMR and mass spectroscopic methods. (c) 2007 Elsevier Ltd. All rights reserved.