Synthesis and Characterization of Metal Phthalocyanine Complex Using Substituted 4-Nitrophthalonitrile Ligand

Abstract

In this research work, four compounds: 4-nitrophthalamide, 4-nitrophthalonitrile and 4-(ciproxy) phthalonitrile and phthalocyanine complex were synthesized. The synthesis began with the nitration in the position 4 of phthalamide which led to the formation of 4-nitrophthalamide. Dehydration by the thionyl chloride in N,N-dimethylformamide (DMF) led to the formation of 4-nitrophthalonitrile and further reaction of ciprofloxacin with 4-nitrophthalonitrile in DMF forms the phthalonitrile derivative, cyclotetramerization of 4-(ciproxy) phthalonitrile in the presence of nickel salt gave substituted metal phthalocyanine complex. The structures of the synthesized compounds were characterized by NMR, FT-IR spectrophotometry and UV-VIS. Melting point of the compounds ware checked by Griffin MFB-590. The melting points of 4-nitrophthalamide and 4-nitrophthalonitrile were found to be 223 oC and 175 oC respectively. Solubility of the compounds was confirmed in some common laboratory solvent (acetone, methanol and DMF). The electronic spectra of nickel phthalocyanine compound in DMF showed intense Q absorption at 690 nm. The thermal stability of the phthalocyanine derivatives was checked by TGA; the phthalocyanine was heated up to 700 oC to determine the degradation temperature. The temperatures at which the phthalocyanine began to exhibit weight loss was 309 oC. It could, therefore, be concluded that the metal phthalocyanines prepared in this study showed suitably high thermal stability and can be used for further analysis.