Electrochemical behaviour of N,N -diphenylbenzidine: synthesis of 4,4 -(5,10-diphenyl-5,10-dihydrophenazine-2,7-diyl)bis(N-phenylaniline)

Organic electrochemical synthesis provides a powerful strategy for the synthesis of organic compounds in both laboratory and industry scale. Electrochemical synthesis of main organic compounds has been extensively employed as a synthetic method in a variety of chemical transformations due to its unique properties such as direct and short‐cut synthetic route, eco‐friendly nature, high current efficiency values, high selectivity and sustainability of the reactions. Selective synthesis of compounds has been a challenging goal for synthetic chemists [1-3]. Our interest in the design and electrochemical synthesis of new compounds prompted us to synthesize new molecules under mild and ambient conditions [4]. The electrochemical dimerization of N,N -diphenylbenzidine (DPB) has been studied. The data indicate that electrochemically generated (N4,N4 -diphenyl-[1,1 -bi(cyclohexylidene)]-2,2 ,5,5 -tetraene-4,4 -diimine) )DPBox( can serve as a Michael acceptor in the reaction with starting molecular (DPB) forms and converts to the corresponding dimer. The mechanism of anodic dimerization of DPB has been successfully performed under constant current condition in good yield and purity in an undivided cell. Controlled-potential coulometry was performed in an aqueous buffer solution (pH= 1.0, c = 0.1 M), containing DPB (1.0 mmol) at Eapp EpA versus Ag/AgCl, to obtain more data on electrochemical oxidation of DPB. The number of the electrons transferred (n) for the anodic oxidation of one molecule of DPB obtained 2 electrons. The results indicate dimerization was happened by ECE mechanism and the obtained spectral data represents synthesis of the corresponding dimer.