The synthesis and spectral properties of novel phthalocyanines with pendant bulky units

Novel phthalocyanines with biphenyl substituents and ester groups that are readily soluble in organic solvents were synthesized from a phthalonitrile derivative obtained by displacement of the –CH proton in 1-chloro-3,4-dicyano-6-(1,1-dicarbethoxymethyl)benzene with 4-(chloromethyl)biphenyl, followed by cyclotetramerization in the presence of metal salts {CuCl2, Pb(CH3COO)2·3H2O, CoCl2 and Zn(CH3COO)2}. Transesterification of malonyl esters occurred during the cyclotetramerization of dinitrile with CuCl2, Pb(CH3COO)2·3H2O in 1-pentanol in the presence of DBU. The structures of the newly synthesized molecules were verified using elemental analysis, 1H NMR, FT-IR, MicroTOF mass and UV–vis spectral data.