Synthesis, crystal structure, Hirshfeld surfaces analysis and electrochemical properties determination of new Schiff base derived from benzidine

A novel Schiff base compound named: N,N'bis(1,2-biphenylethanone) benzidine (BB) has been synthesized by the reaction of benzidine and benzyl under reflux conditions. The structure of the obtained compound was confirmed by FT-IR spectrum, UV-vis, H-1 NMR, C-13 NMR spectroscopies and by the single-crystal X-ray diffraction technique. The compound crystallized in the monoclinic system, space group C2/c with the following unit cell parameters a = 13.4126(8)(& Aring;), b = 10.6584(7)(& Aring;),c = 21.1768(12)(& Aring;) and beta=103.549(4)degrees, and Z = 8, V = 2943.1(3) (& Aring;(3)), T = 293(2) K. The final R1 was 0.0317 (I >2 sigma(I)) and wR2 was 0.100 (all data). Then, we present a detailed analysis of the structure of N,N'bis(1, 2-biphenylethanone) benzidineby using Hirshfeld topology analysis. The graphical tools based on Hirshfeld surfaces and two-dimensional (2D) fingerprint plots have proven useful for visualize and analyze intermolecular interactions in polymorphs of molecular crystals. The electrochemical properties of the studied Schiff base have been investigated by cyclic voltammetry in dimethylformamide containing tetraethylammonium perchlorate as a supporting electrolyte at a scan rate of 100 mV.s(-1). The obtained redox potentials of the compound (BB) confirm also the formation of the azomethine group.