Metal-free and metallophthalocyanines appending with eight 12-crown-4 ethers

The metal-free phthalocyanine 2 was synthesized from the 4,5-bis(1,4,7,10-tetraoxacyclododecan-2-ylmethoxy)phthalonitrile 1 in the presence of a strong base in n-pentanol. The synthesis of metallo derivatives [Ni(II), Co(II), Cu(II)] of phthalocyanines obtained from corresponding phthalonitrile derivative 1 and in the presence of the anhydrous divalent metal salts (NiCl2, CoCl2 and CuCl2) were described. The thermal stabilities of the metal-free and metallophthalocyanines were determined by thermogravimetric analysis. These phthalocyanines were good soluble in organic solvents such as chloroform, dichloromethane, tetrahydrofuran and DMF. The products were characterized by elemental analysis, IR, 1H NMR, UV-vis and MS spectral data.