Synthesis and characterization of polyfluoroalkoxysulfonyl phthalonitrilesand corresponding zinc and cobalt phthalocyanines

The reaction of 1,2-dicyanobenzene-4-sulfonyl chloride with different polyf luoro alcohols leads to the formation of 1,2-dicyano-4-polyfluoroalkoxysulf onyl benzenes. The tetramerization of such nitriles in the presence of zinc or cobalt salts results in the corresponding phthalocyanines. The influenc e of solvent and substituents on the aggregation of the phthalocyanine comp lexes was studied by electronic spectroscopy. The polyfluoroalkoxysulfonyl groups were shown to stabilize both HOMO and LUMO of the complexes in compa rison with alkoxy- or polyfluoroalkoxy-substituted analogs. The first oxida tion potential for zinc-containing complexes was estimated as 1.47-1.65 V. (C) 1999 Elsevier Science Ltd. All rights reserved.