Synthesis and characterization of new phthalocyanine derivatives via click reaction and investigation of their electrochemical properties

Phthalocyanines are the macroheterocyclic compounds comprising four isoindole units connected to each other with the nitrogen atom in the meso position. Phthalocyanines were generally synthesized with phthalonitriles and diffrent derivatives of these (phthalimide, phthalic acid etc.) or from addition products of these as non-metallic or with metal salts producing metal complexes at high temperatures. Changing the metal ion in the center and peripheral substituents new phthalocyanines can be obtained. Phthalocyanines that are completely synthetic materials have applications on areas such as dyes and pigments, energy conversion, electrophotography, optical data storage, an infrared dye for laser technology and photodynamic therapy of cancer. Recently, 1,3-dipolar ring addition between azides and alkynes is a handy method with properties such as rapid, reproducible, low side product and high tolerance reaction conditions, and havin g great demand as "click" reaction. Prepearation of new macromolecules with Cu(I) catalysed "click" reaction a large number of study have been reported and also applications of these studies to the phthalocyanines derivatives have been made. Examination of electron transfer properties of the newly synthesized phthalocyanine complex is required for advanced applications that can be run. Electron transfer properties of phthalocyanines depends on conjugated π-electron system of phthalocyanines, interaction between phthalocyanine and central metal salt and number and type of substituents that they have. In this study a new alkyl-end ligand was synthesized from propargyl alcohol and 4-nitrophthalonitrile as first step. The azide compound N-(2-azidoethyl)-phthalimide which attached to this end were synthesized from N-(2-Bromoethyl)-phthalimide and sodium azide. Then, the novel ligand was synthesized as a result of "click" reaction 1-3 dipolar ring addition of azide functional group and terminal alkene group with the Cu (I) and Cu(II) catalysts. Phthalocyanines are obtained by the reaction of these substance with the metal salts in the conventional method. Molecular structure of the new synthesized material were characterized with UV-Vis, FT-IR, 1H-NMR, 13C-NMR and MALDI-TOF mass spectrum. Finally, electrochemical properties of these compounds were studied comperatively. Keywords: Phthalocyanine, metallophthalocyanine, catalyzer, click, electrochemistry