Synthesis and characterization of new metal-free and metallophthalocyanines fused α-methylferrocenylmethoxy units

Synthesis of metal-free and metallophthalocyanines bearing alpha-methylferrocenylmethoxy units was described. Precursor 3 required for the preparation of phthalocyanines 4-9, was synthsized by the nucleophilic aromatic substitution reaction between alpha-methylferrocenylmethanol and 4-nitrophthalonitrile in dry DMF. The metal-free phthalocyanine 4 was prepared from 4-(alpha-methylferrocenylmethoxy)phthalonitrile 3 in 1-pentanol with a catalytic amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Metallophthalocyanines (M = Zn, Cu, Co, Ni and Pb) were prepared by cyclotetramerization reaction of phthalonitrile with appropriate materials. The phthalonitrile, metal-free and metallophthalocyanines were characterized by H-1 and C-13 NMR, FT-IR UV-Vis and mass spectral data, as well as elemental analyses, which were consistent with the proposed structures.