Synthesis and properties of new phthalocyanines with tertiary or quaternarized aminoethylsulfanyl substituents

Metal-free- and metallo-phthalocyanines (M = Ni or Zn) carrying four dimethylaminoethylsulfanyl- or trimethylaminoethylsulfanyl- groups on peripheral positions have been synthesized from the corresponding phthalonitrile derivatives in the presence or the absence of the anhydrous metal salt [NiCl2 or Zn(CH3COO)(2)]. The new compounds have been characterized by elemental analyses, IR, NMR, and electronic spectroscopy and mass spectra. Phthalocyanines with quaternarized amino groups are soluble in aqueous solution over a wide pH range and these molecules are present as aggregated species in solution as confirmed by the blue shift of Q bands in their electronic spectra.