An Efficient Synthesis, Spectroscopic Characterization, and Optical Nonlinearity Response of Novel Salicylaldehyde Thiosemicarbazone Derivatives

Abstract

In this study, seven derivatives of salicylaldehyde thiosemicarbazones (1–7) were synthesized by refluxing substituted thiosemicarbazide and salicylaldehyde in an ethanol solvent. Different spectral techniques (UV–vis, IR, and NMR) were used to analyze the prepared compounds (1–7). Accompanied by the experimental study, quantum chemical studies were also carried out at the M06/6-311G­(d,p) level. A comparative analysis of the UV–visible spectra and vibrational frequencies between computational and experimental findings was also performed. These comparative data disclosed that both studies were observed to be in excellent agreement. Furthermore, natural bond orbital investigations revealed that nonbonding transitions were significant for the stability of prepared molecules. In addition, frontier molecular orbital (FMO) findings described that a promising charge transfer phenomenon was found in 1–7. The energies of FMOs were further used to determine global reactivity parameters (GRPs). These GRP factors revealed that all synthesized compounds (1–7) contain a greater hardness value (η = 2.1 eV) and a lower softness value (σ = 0.24 eV), which indicated that these compounds were less reactive and more stable. Nonlinear optical (NLO) evaluation displayed that compound 5 consisted of greater values of linear polarizability ⟨α⟩ and third-order polarizability ⟨γ⟩ of 324.93 and 1.69 × 105 a.u., respectively, while compound 3 exhibited a larger value of second-order polarizability (βtotal) of 508.41 a.u. The NLO behavior of these prepared compounds may be significant for the hi-tech NLO applications.

Exploration of Photophysical and Nonlinear Properties of Salicylaldehyde-Based Functionalized Materials: A Facile Synthetic and DFT Approach

“…The detailed synthetic scheme of TSCs was also discussed in our previously published article. 67 5.2. (E)-N-Benzyl-2-(5-choro-2hydroxybenzyidene)hydrazinecarbothioamide (1).…”

“…The extent of the reaction was observed via thin-layer chromatography during the reaction. The detailed synthetic scheme of TSCs was also discussed in our previously published article …”

New Potential Agents for Malignant Melanoma Treatment—Most Recent Studies 2020–2022

“…Thiosemicarbazones and thiosemicarbazides are scaffolds with a privileged place in medical chemistry. Their derivatives exert a wide spectrum of activity, including anticancer activity [ 116 , 117 ]. Its derivatives with anti-melanoma activity are presented in Figure 12 .…”

Antispasmodic activity of novel 2,4-dichloroanilinium perchlorate hybrid material (I): X-ray crystallography, DFT studies, and molecular docking approach

“…The computational simulations of the vibrational speci cities of the studied compound were attained at the M06-2X/6-311 + + G (2df, 2pd) level of computations. 56 fundamental vibrational moods are noticeable based on the n-6 rule [44][45]. For comparison with the experimental data, statistical analysis based on regression coe cient R2 was utilized to effectively assess the level of coherence of the optimized structure with the experimental data.…”