Syenthesis and characterization of new bis-phthalocyanine compounds and investigation of thermal properties

Phthalocyanines are macrocycle compounds having delocalized 18-π electron that are made of four iminoisoindol units. Due to the interesting electronic structures, thermal stabilities, physical and chemical properties, these compounds have application potentials in various technological areas. In this work, first 4-nitrophthalonitrile compound was synthesized from phthalimide, followed by the reaction of 4-nitrophthalonitrile with 2-methyl hydroquinone, 2,3,5-trimethylhydroquinone, 2-chloro hydoquinone, chloranilic acid, tetrachlorohydroquinone, tert-butylhydroquinone, 2,5-di-tert-butylhydroquinone, 4,4'-(2-methyl-1,4-phenylene dioxy)diphthalonitrile, 4,4'-(2,3,5-trimethyl-1,4-phenylenedioxy)diphthalonitrile, 4,4'-(2-chloro-1,4-phenylenedioxy)diphthalonitrile, 4,4'-(2,5-dichloro-3,6-dioxo-1,4-cyclohexa diene-1,4-dioxy)diphthalonitrile, 4,4'-(tetrachloro-1,4-phenylenedioxy)diphthalonitrile, 4,4'-(2-tert-butyl-1,4-phenylenedioxy)diphthalonitrile, 4,4'-(2,5-di-tert-butyl-1,4-phenylenedioxy)diphthalonitrile compounds were synthesized. Structures of the synthesized compounds have been characterized by micro analysis, melting point, FT-IR, 1H-NMR and 13C-NMR spectroscopy. Metal bisphthalocyanine complexes were obtained by using newly synthesized diphthalonitrile compounds with Co(II), Ni(II), Cu(II) and Zn(II) acetate salts in N,N'-Dimethylformamide (DMF) under Argon atmosphere. Metal free bisphthalocyanine compounds were also synthesized from these diphthalonitrile compounds by the catalysis of 1,8-Diazabisiklo[5.4.0]undec-7-ene (DBU) base in N,N'-Dimethylformamide (DMF) under Argon atmosphere. Analysis of the phthalocyanine compounds were performed by micro analysis, FT-IR and UV/visible spectroscopic techniques. Thermal behaiviour of the complexes were investigated by thermogravimetric analysis (TGA) and differancial thermal analysis (DTA) methods.