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.