Synthesis and characterization of polyfluoroalkoxysulfonyl phthalonitriles and corresponding zinc and cobalt phthalocyanines

The reaction of 1,2-dicyanobenzene-4-sulfonyl chloride with different polyfluoro alcohols leads to the formation of 1,2-dicyano-4-polyfluoroalkoxysulfonyl benzenes. The tetramerization of such nitriles in the presence of zinc or cobalt salts results in the corresponding phthalocyanines. The influence of solvent and substituents on the aggregation of the phthalocyanine complexes was studied by electronic spectroscopy. The polyfluoroalkoxysulfonyl groups were shown to stabilize both HOMO and LUMO of the complexes in comparison with alkoxy- or polyfluoroalkoxy-substituted analogs. The first oxidation potential for zinc-containing complexes was estimated as 1.47¯1.65 AV.