Synthesis and characterization of new metal-free and phthalocyanine nickel(II) complex containing macrocyclic moieties

A new metal-free and metallophthalocyanine carrying four 1,1′-biphenyl crown ether units on peripheral positions have been synthesized. Metal-free phthalocyanine was prepared by the reaction of 2,3-(4′,5′-dicyanobenzo)-11,12:13,14-di(1′,2′-biphenyl)-1,4,7,10,15,18-hexaoxacycloeicosa-2,11,13-triene with dry 2-(N,N-dimethylamino)ethanol under reflux. Metal derivative of phthalocyanine was also synthesized by the anhydrous NiCl2 and metal-free phthalocyanine in dry quinoline under reflux. The target symmetrical phthalocyanines were separated by column chromatography and characterized by elemental analysis, 1H, 13C NMR, IR, UV–visible and FAB mass spectroscopies.