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

Abstract

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 ¹H and ¹³C 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 ωB97X-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.

GRAPHICAL ABSTRACT

KEYWORDS:

• Thiazolidinone
• spectroscopy
• NLO
• hyper-Rayleigh scattering
• DFT

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

The investigation was supported by the Algerian Ministry of Higher Education and Scientific Research as well as the directorate general for scientific research and technological development.