Synthesis, characterization and investigation of electrochemical properties of containing acetylene group new phthalocyanine derivatives

Macrocycle compunds are the compounds that contain a minimum of 9 members and 3 heteroatoms. Phthalocyanines, which are one of the coordination compounds containing macrocycles ligands, were discovered by accident at the beginning of the 20th century. Besides phthalocyanines blue and green pigment properties, they have an outstanding stability against light, excessive heat, strong acids and alkalis other than strong oxidation agents, and are insoluble in some organic solvents and water. Unsubstituted and substituted phthalocyanines are widely used as pigment and dyes. They have been used as photoconducting agents in photocopying machines, as electrochromic display device, as photodynamic reagents for cancer therapy and other medical applications. Other applications include using optical computer read-write disc and related information storage systems, as laser dyes, in liquid-crystal color display applications, in photovoltaic cell elements, as catalysts for control of sulfur effluents, for oxidizing saturated hydrocarbons at low temperature, and for increasing the octane rate of gasoline, etc. so phthalocyanines can find many potential usage in industry. Recently, 1,3-dipolar cycloadditions, from the reactions between azides and alkynes known as ?click reaction?, have been recognized as a useful synthetic methodology due to their being fast, quantitative, reproducible, resistant to side reactions, and highly tolerant to reaction conditions. Although numerous applications of click chemistry for the preparation of novel macromolecules have been frequently reported, only a few examples are available for phthalocyanine derivatives. In this study, firstly, a novel phthalonitrile derivative was synthesized from propargyl alcohol and 3 nitrophthalonitrile. Metallophthalocyanines were obtained its cyclotet ramerization with classical method in the presence of Co(II) and Zn(II) metal salts. Also zinc-phthalocyanine was synthesized using microwave irradiation as alternatively classical method. Moleculer structures of new products have been characterized by FT-IR, UV-Vis, 1H NMR, 13C NMR and MALDI-TOF Mass Spectroscopy methods. At last, electrochemical and spectroelectrochemical properties of these compounds were investigated, comparatively. Keywords: phthalonitrile, zinc, cobalt, microwave, electrochemistry