New phthalocyanines bearing tetra(hydroxyethylthio) functionalities

Zn(II), Co(II), Ni(II) and metal-free phthalocyanines (2–5) bearing a hydroxyethylthio substituent on each benzo group were prepared from 4-(hydroxyethylthio)phthalonitrile (1) and the corresponding divalent metal salt. The reactivity of the hydroxyethyl groups was demonstrated by esterification of phthalocyanine derivatives (2–5) with acetic anhydride at reflux temperature and acetylated phthalocyanine compounds (6–9) were obtained. The new compounds have been characterized by elemental analyses, IR, UV–vis, mass and 1H NMR spectroscopy.