Synthesis and characterization of new polyfluorinated dendrimeric phthalocyanines

The synthesis of new polyfluorinated dendrimeric metallophthalocyanines (M = Zn, Ni, Co) bearing 3,5-bis(2',3',4',5',6'-pentafluorobenzyloxy)benzyloxy moieties (2-4) was achieved by cyclotetramerization of phthalonitrile derivative 1 in the presence of zinc, nickel or cobalt salts in DMF. All the target phthalocyanines were separated by column chromatography and their spectroscopic, fluorescence and energy transfer properties, and aggregation behavior were investigated in different solvents and at different concentrations in chloroform. The compounds were characterized by Fourier transform-infrared, fluorine, proton and carbon nuclear magnetic resonance, mass, ultraviolet-visible and fluorescence spectral data. The phthalocyanines (2-4) were extremely soluble in various organic solvents, such as tetrahydrofuran, acetone and dichloromethane. (C) 2010 Elsevier Ltd. All rights reserved.