Structural, spectral, electrochemistry, thermal properties and theoretical studies on 4-[N, N-di(4-tolyl)amino] benzaldehyde-2-chloro benzoylhydrazone

•4-[N, N-di(4-tolyl)amino] benzaldehyde-2-chloro benzoylhydrazone were synthesized and characterized.•The photophysical, thermostability properties of the titled compound were found to be distinctively modified by benzoylhydrazone structure.•DFT calculations and experimental results were coincided on structure, energy gap and electrochemistry.•The hydrogen bonding interactions within sheets and π–π interactions 3D network confirmed the title compound can be used as amorphous material in nonpolar solvents.

The title compound 4-[N, N-di(4-tolyl)amino] benzaldehyde-2-chloro benzoylhydrazone (C28H24ClN3O, Mr = 453.96) was synthesized by the reaction of 4-[N, N-di(4-tolyl)amino] benzaldehyde with 2-chlorobenzohydrazide, and its structure was characterized by IR, 1H NMR, 13H NMR, high-resolution mass spectrometry and single-crystal X-ray diffraction. The crystal belongs to Monoclinic, space group P2(1)/n with a = 12.626(3), b = 12.609(3), c = 15.837(3) Å, β = 90.00(3)°, Z = 5, V = 2512.5(9) Å3, Mr = 453.95, Dc = 1.280 g/cm3, μ = 0.183 mm−1, F(0 0 0) = 1024, R = 0.0432 and wR = 0.1087. X-ray analysis revealed that one of the benzene ring and acylhydrazone were essentially planar, the 2-chloro benzene ring and amide were non-planar, the torsion angles C(1)C(6)C(7)O(1) and C(5)C(6)C(7)O(1) are 61.4(5)° and −114.4(4)°. The thermal stability studies indicate that the title compound is stable up to 341.1 °C. The spectral, electrochemistry properties and theoretical studies show that the title compound is a good candidate for the charge-transporting materials.