The synthesis and characterization of functionalized polyfluorinated phthalocyanines

Abstract

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)phthalonitrile 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, 1H NMR, 19F NMR and mass spectroscopic methods.