Non-ionic peripherally substituted soluble phthalocyanines: Synthesis characterization and investigation of their solution properties

摘要

Novel tetra aminopropylamid substituted phthalocyanineswere synthesized as zinc(II), cobalt(II), copper(II) and manganese(II) metallophthalocyanines. The synthesis of the phthalocyanines 3–6 was achieved by the tetramerization of 4-subtituted phthalonitrile, 2-(3,4-dicyanophenoxy)ethyl-N-(3-dimethylaminopropyl)carbamate (2), prepared via the nucleofilic aromatic substitution of 4-nitro phthalonitrile and 2-hydroxyethyl-N-(3- dimethylaminopropyl) carbamate (1). Solution properties of the prepared phthalocyanines were investigated by the examination of their UV–vis spectra. The zinc Pc showed surprisingly high solubility in water. The aggregation properties of the Pcs were examined in different organic solvents and water. The substituents on the periphery position of the phthalocyanine molecules acted as non-ionic surfactant and increased the solubility in hydrophilic solvents and water. Quaternization of these groups improved the solubility, as well.