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

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 (eta = 2.1 eV) and a lower softness value (sigma = 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 and third-order polarizability of 324.93 and 1.69 x 10(5) a.u., respectively, while compound 3 exhibited a larger value of second-order polarizability (beta(total)) of 508.41 a.u. The NLO behavior of these prepared compounds may be significant for the hi-tech NLO applications.

Automated summary

In this study, seven derivatives of salicylaldehyde thiosemicarbazones were synthesized and analyzed using spectral techniques and quantum chemical studies, showing excellent agreement between experimental and computational findings. The investigation revealed the significance of nonbonding transitions for the stability of prepared molecules and the presence of a promising charge transfer phenomenon. Furthermore, the global reactivity parameters indicated that the synthesized compounds were less reactive and more stable, with potential significance for high-tech NLO applications.