The synthesis of some phthalocyanines derived from bulky substituted phthalonitriles

Phthalocyanine precursors were prepared by displacement of the –CH proton in 1-chloro-3,4-dicyano-6-(1,1-dicarbethoxymethyl) benzene with 1-(chloromethyl)-2-methyl benzene and 1-(chloromethyl)-4-methyl benzene. Metallo-phthalocyanines were obtained by cyclotetramerization in the presence of template metal salts {Zn(CH3COO)2, CoCl2, CuCl2, and Pb(CH3COO)2·3H2O} that possessed substituents to enhance the solubility of the macrocycle and reduce its propensity to aggregate in solution. The structures of the newly synthesized molecules were proposed according to elemental analysis and 1H NMR, FT-IR, Micro-TOF mass, MALDI-TOF mass and UV–vis spectral data.