Synthesis, characterization and DFT calculations of linear and NLO properties of novel (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one

In the present investigation, we report a combined experimental and theoretical study of (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one synthesized by the Knoevenagel condensation of rhodanine with an aromatic aldehyde in good to excellent yields. A variety of physicochemical techniques were employed for characterization of the synthesized compound including H-1 and C-13 nuclear magnetic resonance (NMR), scanning electron microscopy (SEM), energy dispersive X-Ray analysis (EDX) and ultraviolet-visible (UV-VIS) spectroscopy. The geometry optimization, frontier molecular orbital energies and the energy gap of the title compound in the ground state have been investigated with density functional theory (DFT) method at different functionals (B3LYP, CAM-B3LYP, M05-2X, PBE0, and omega B97X-D) in conjunction with different basis sets. We also calculate their dipole moment, linear polarizability, and first hyperpolarizability to elucidate the nonlinear optical (NLO) activity. The HOMO-LUMO energy gap obtained from the PBE0 functional agrees with the experimental data deduced from the UV-VIS measurement. The resulting compound shows a high hyper-Rayleigh scattering (HRS) first hyperpolarizability, which makes it suitable for optoelectronic and optical devices.