Synthesis and characterization of a new phthalonitrile and its phthalocyanines bearing diamagnetic metals

The compounds which were called phthalocyanines discovered as an accident in 1907, by Braun and Tcherniac during preparation of o-cyanobenzamide from phthalimide and acetic acid. Generally, these compounds are blue, green coloured, resistant to heat, light and acids, but they have less solubility. Phthalocyanines, have widely usage in different areas. For example, press ink as a dye and pigment, making coloured metal and plastic surfaces, laser technology, as optical and elektrical materials, photodynamic cancer cure and chemical sensor. Phthalocynanines are usually synthesized starting from the appropriate phthalonitriles and their derivatives or their substitution yield as metal-free phthalociyanine and metallophthalocyanines which obtained especially in high temperatures with the presence of a suitable anhydrous metal salt. In this study, 4-(2,6-dimethylphenylthio)phthalonitrile was synthesized from a mixture of 4-nitrophthalonitrile and 2,6-dimethylbenzenethiol and obtained as single crystal form suitable for X-ray analysis. In the final stage, metal free and metallophthalocyanines were synthesized by the interaction of the compound phthalonitrile in n-amyl alcohol/DBU with MgCl2, Zn(CH3COO)2 and Pd(CH3COO)2. The structures of the new products were characterized by elemental analysis, FT-IR, UV, 1H NMR and Mass spectrometry.