Synthesis and characterization of new metal-free and nickel(II) phthalocyanines containing tetraazatrioxa macrotricyclic moieties

Novel metal-free and nickel(II) phthalocyanines bearing four tetraazatrioxa macrotricycles on peripheral positions were synthesized. Metal-free phthalocyanine was prepared by the reaction of 9,10-(2′,3′-dicyano)-8,11,21-trioxa-1,5,14,18-tetraazatrioxa [12,9,2.25,18]heptacosane (4) with dry 2-(N,N-dimethylamino)ethanol under reflux. The nickel(II) phthalocyanine was synthesized by the anhydrous NiCl2 and compound (4) in dry ethylene glycol under reflux. We also used compound (4) and metal-free phthalocyanine (5) in solvent extraction for some transition metal ions. The new symmetrical compounds were characterized by elemental analysis, 1H, 13C NMR, IR, UV–vis and mass spectral data.