The synthesis and characterization of functionalized polyfluorinated phthalocyanines

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.