Electrochemical investigation of 2-[8-hydroxyquinoline-5-yl)azo]benzo[c]cinnolineon a platinum electrode in dimethysulfoxide

2-[8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline was synthesized for the rst time and shown to possesselectrochromic characteristic, i.e. changing color during the forward and back electrolysis at {1.35 V and 0.00 V,respectively, in DMSO medium. Therefore, the electrochemical investigation of this compound appears to be worthwhile.The electrochemical reduction of 2-[8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline was investigated by cyclic voltam-metry, controlled potential electrolysis, and chronoamperometry techniques in the presence of 0.10 mol L1tetrabutylam-monium tetra uoroborate in dimethyl sulfoxide at platinum electrode. 2-[8-Hydroxyquinoline-5-yl)azo]benzo[c] cinnolinedisplays three sharp cathodic peaks and three anodic peaks in the cyclic voltammogram. The diffusion coefficients andthe number of electrons transferred were calculated by using an ultramicroelectrode and platinum electrode. The num-ber of transferred electrons was found to be one for each peak. The standard heterogeneous rate constant for reductionwas calculated by the Klingler{Kochi technique. The electrochemical reduction mechanism of 2-[8-hydroxyquinoline-5-yl)azo]benzo[c]cinnoline was also investigated by using various electrochemical techniques, such as bulk electrolysis, andspectroscopic methods, like electron spin resonance spectroscopy. Bulk electrolysis results also provided evidence foreach peak belonging to reduction of one electron, two of which were con rmed by electron spin resonance spectroscopy.This new chemical is found to be an electrochromic substance.

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