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Synthesis, Absorption and Emission Behaviour, Solvation, AIM, Topology, and Docking Studies on 4-(((perfluorophenyl)

V Tamilselvi^1,2, Aamal A Al-Mutairi³, M Arivazhagan⁴

¹Department of Physics, Pioneer Kumaraswamy College, Kanyakumari District, Nagercoil, 629 003, Tamil Nadu, India.

Journal of Fluorescence

|August 22, 2025

Abstract:

This work aims to synthesize 4-(((perfluorophenyl) methylene)amino)-N-(thiazol-2-yl) benzene sulfonamide (PFTH) and characterize it using various instrumental techniques such as UV-visible (UV-vis), fluorescence, Fourier-transform-infrared (FTIR), Raman, and nuclear magnetic resonance (NMR) spectroscopy analyses, respectively. The density functional theory (DFT) calculations have been performed using correlation-consistent polarized valence double-zeta (cc-pVDZ) basis sets and Becke, 3-parameter Lee-Yang-Parr (B3LYP) functionals, respectively. In this study, we used Gauge-Including Atomic Orbitals (GIAO) to determine the computational techniques for nuclear magnetic resonance (¹³C NMR and ¹H NMR) spectroscopy. The C-S bond lengths have been measured as follows: C24-S8 = 1.75 Å, C27-S28 = 1.73 Å, and C17-S20 = 1.77 Å, respectively. A higher absorption wavelength (307 nm) has been observed in the gas phase due to the solvent interaction. The synthesized PFTH displays two emission peaks at the excitation wavelengths of 356 nm and 648 nm, respectively, in DMSO solvent. The calculated energy gap of about ~ 7.6047 eV in the gas phase has been determined using frontier molecular orbital (FMO) analysis. The estimated value is comparatively lower than that in the solvent environments, such as water, chloroform, and DMSO. Electrophilic and nucleophilic regions are revealed by the molecular electrostatic potential (MEP) of the PFTH. The natural bond orbital (NBO) analysis of the PFTH compound at LP(2)S28→π∗(C24-N25) had the highest stabilization energy (E(2)) value of about 47.87 kcal/mol. Topological analyses such as electron localization function (ELF), localized orbital locator (LOL), and average localized ionization energy (ALIE), respectively, were conducted in this study. In addition, non-covalent interaction (NCI) and atoms in molecules (AIM) studies revealed that hydrogen bonds formed between C15-H31 and N25. A molecular docking study was also performed on the molecules, and the lowest binding energy was observed at - 6.67 kcal/mol.

Keywords:

DFT analysis DORI Molecular docking Schiff base compound Solvation (IEFPCM)

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