Synthesis, characterization, and aggregation properties of functionalized polyfluorinated metallo-phthalocyanines

The reaction of 4-(2',3',4',5',6'-pentafluorobenzyloxy)phthalonitrile with 2,2,3,3,4,4,5,5-octafluoropentanol leads to the formation of 4-[2',3',5',6'-tetrafluoro-4'-(octafluoropentoxy)benzyloxy]phthalonitrile. The reaction was achieved by regioselective substitution reaction of the p-fluorine atoms of pentafluorobenzyloxy group by perfluoroalkoxy group. The tetramerization of the new dinitrile derivative in the presence of zinc, cobalt, copper or manganese salts results in the corresponding phthalocyanines. The prepared compounds have been characterized by elemental analyses, FT-IR, UV-vis, H-1 NMR, C-13 NMR, F-19 NMR and mass spectroscopies, consistent with the proposed structures. The influence of solvent and concentrations on the aggregation of the phthalocyanine complexes was studied by electronic spectroscopy.