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

Author(s)

Khalid, Muhammad ^[1] ; Jawaria, Rifat ^[1] ; Khan, Muhammad Usman ^[2] ; Braga, Ataualpa Albert Carmo ^[3] ; Shafiq, Zahid ^[4] ; Imran, Muhammad ^[5] ; Zafar, Hafiz Muhammad Ahmad ^[1] ; Irfan, Ahmad ^{[5, 6]}

Affiliation

^[1] Khwaja Fareed Univ Engn & Informat Technol, Dept Chem, Rahim Yar Khan 64200 - Pakistan

^[2] Univ Okara, Dept Chem, Okara 56300 - Pakistan

^[3] Univ Sao Paulo, Dept Quim Fundamental, Inst Quim, BR-05508000 Sao Paulo - Brazil

^[4] Bahauddin Zakariya Univ, Inst Chem Sci, Multan 60800 - Pakistan

^[5] King Khalid Univ, Fac Sci, Dept Chem, Abha 61413 - Saudi Arabia

^[6] King Khalid Univ, Res Ctr Adv Mat Sci RCAMS, Abha 61413 - Saudi Arabia

• Document type: Journal article
• Source: ACS OMEGA; v. 6, n. 24, p. 16058-16065, JUN 22 2021.
• Web of Science Citations: 0

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 (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 <alpha > and third-order polarizability <gamma > 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. (AU)

• FAPESP's process: 15/01491-3 - Theoretical study of cross-coupling reactions: homogeneous and heterogeneous catalysis
• Grantee: Ataualpa Albert Carmo Braga
• Support Opportunities: Regular Research Grants
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants