SYNTHESIS AND CHARACTERIZATION OF PHTHALOCYANINES WITH NON-IONIC SOLUBILIZING GROUPS

ABSTRACT Two new mono substituted phthalonitrile derivatives (1) and (2) have been prepared by a nucleophilic displacement reaction of 4-nitrophthalonitrile with ethylene glycol or tetraethylene glycol. Novel metal-free and metallated phthalocyanines (pcs) have been synthesized by cyclotetramerization of these phthalonitriles in the presence of hydroquinone or anhydrous divalent metal salt to form Ni(II), Co(II), Cu(II) and Zn(II) adducts. The newly synthesized pcs are very soluble in polar solvents such as H2O to THF. The complexes have been characterized by elemental analyses, IR, 1H and 13C NMR, and UV-Vis spectra.