Unveiling the multifaceted potential of (E)-N-(4-Chlorophenyl)-1-(thiophen-2-yl) methanimine with special reference to solution-state fluorescence, synthesis, electronic structure, antimicrobial, antibiofilm, larvicidal activities, toxicity, docking and dynamics

Abstract

Schiff bases exhibit distinctive characteristics in the realm of chemistry, physics, and medicine, rendering them highly efficacious in the field of biology. A Schiff base was synthesized by reacting 4-chloroaniline with thiophene-2-carboxaldehyde, and its structure was subsequently optimized using density functional theory (DFT). We conducted experimental simulations and validations of the IR, UV, and NMR spectra. The compound formation was confirmed through the utilization of FTIR, UV–VIS, 1HNMR, and 13CNMR analyses. The observed fluorescence intensities at wavelengths of 438.28 and 666.83 nm provided indications of its inherent fluorescence properties. A conspicuous alteration in the thermogravimetric analysis (TGA) plot within the temperature range of 250 °C to 315 °C was indicative of a chemical metamorphosis. The compound exhibited an energy gap of 3.97 electron volts (eV). In the MEP graph, the blue regions denoted electron-deficient areas, whereas the red regions represented electron-abundant regions. In the context of natural population analysis, the hydrogen atoms exhibit positive charges, which are associated with electron transfer phenomena. The optimized compound exhibited nitrogen and chlorine atoms with negative charges, functioning as electron donors. The utilization of NBO (Natural Bond Orbital) analysis and spectral analysis unveiled the occurrence of electron transfers within the molecular framework. The ELF diagrams illustrate the presence of hydrogen by utilizing the colour red, while carbon and nitrogen are represented by the colour blue. The carbon atoms exhibited a blue hue in the LOL diagram, indicating a state of electron deficiency. Non-covalent interactions were exemplified in RDG maps. It exhibited superior antimicrobial efficacy against both bacteria and fungi, surpassing that of amoxicillin The compound exhibited a moderate level of antibiofilm activity, with an IC50 value of 158.9 μg/ml. Additionally, it demonstrated larvicidal effects that were dependent on the concentration. The antimicrobial properties of the compound were confirmed through molecular docking and dynamic simulation. The insilico assessments conducted against toxicity models have revealed a notable absence of toxicity and a commendable level of tolerance.