Electrochemical and structural analysis of a novel symmetrical bis-Schiff base with herringbone packing motif

•Symmetrical bis-Schiff base.•X-ray, FTIR, NMR, elemental analysis, TG/DSC, voltammetry.•Electrochemical analysis.•Herringbone structural motif.

A novel symmetrical bis-Schiff base was synthesized and characterized by means of single crystal X-ray diffraction, FT-IR and NMR spectroscopy, elemental, TG/DSC and electrochemical analysis. The synthesized molecule represents a rare example of symmetrical bis-Schiff base with uncondensed primary amino group as the final reaction product. The molecule is planar, with largest deviation of aminophenyl benzene ring from the plane calculated through the aliphatic chain in the amount of 4.93(1)°. In the crystal, the molecules are primarily linked by hydrogen bonds involving primary amino groups and weak CH⋯π interactions. Consequently, these interactions are arranging molecules into herringbone packing motif. The FT-IR and NMR spectra indicated presence of both imino and amino groups in dissolved and solid state, therefore confirming consistency of the studied material and also molecular structure determined by X-ray diffraction. Electrochemical study has shown that the oxidation of the investigated Schiff base is irreversible, diffusion controlled process and that the oxidation products are adsorbed on the glassy carbon electrode surface.

Graphical abstractCrystal structure of the novel synthesized Shiff base, (1E)-1-N-{[4-(4-{[(E)-N-(2-aminophenyl)carboxyimidoyl]phenoxy}butoxy)phenyl]methylidene}benzene-1,2-diamine.Figure optionsDownload full-size imageDownload as PowerPoint slide