Exploring the structure and dynamics of a fluorescent schiff base (1E,1′E)-1,1′-(1,4-phenylene) bis(N-(4-chlorophenyl) methamine: Synthesis, spectroscopic analysis, thermal, electronic and crystallographic study with biological applications

• Published in: Journal of molecular structure Vol. 1312; p. 138546
• Main Authors: Rajimon, K.J., Alzahrani, Abdullah Y., Nair, Deepthi S. Rajendran, Venkatesh, Deeksheetha Prabhu, Thomas, Renjith
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.09.2024
• Subjects: Antimicrobial activity; Molecular docking; Molecular dynamics; Schiff base; Toxicity; Schiff base; Molecular dynamics; Antimicrobial activity; Toxicity; Molecular docking
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.138546

•The compound (1E,1′E)−1,1′-(1,4-phenylene) bis(N-(4-chlorophenyl) methamine is successfully synthesized and characterised.•Thorough examination of the electronic structure and physicochemical characteristics.•Demonstrates antimicrobial activities against bacteria and fungi.•Performed molecular docking and molecular dynamics simulations.•In silico toxicity assessments using seven different models. Schiff bases have emerged as attractive biological agents with a wide range of uses due to the extraordinary physical, chemical, and pharmacological characteristics that they possess. This study focuses on the effective synthesis of a Schiff base that is produced from 4-chloroaniline and terephthaldehyde. The success of this synthesis is supported by a variety of spectroscopic methods and Single crystal XRD analysis. The chemical that was synthesised had significant fluorescence qualities, with measured values at 457.13, 481.49, and 524.15 nm, highlighting the fact that it has the potential to be utilised in a variety of applications within the field. Using thermogravimetric analysis, the thermal stability of the compound was studied, which revealed an excellent stability at 399 °C. Thermal stability is an essential component of compound usefulness. Molecular insights were obtained by the utilisation of Density Functional Theory, which revealed an energy gap of 1.70 electron volts (eV) and electrophilic behaviour in certain atoms. The distribution of charges was brought to light through the use of Mulliken charges and molecular electrostatic potential analysis, which brought attention to the distinctive qualities of the subject molecule. An examination of the electron localization function revealed that the electron density inside carbon, nitrogen, and chlorine atoms had been delocalized. Additionally, the localised orbital locator wave function and reduced density gradient maps offered vital insights into the non-covalent interactions that were taking place within the system under investigation. In the course of the evaluation of antimicrobial efficacy, it was discovered that the chemical exhibited more powerful antibacterial activity against gram-positive B. subtilis than the conventional antibiotic amoxicillin. The antibacterial findings were further supported by molecular docking tests, which involved using particular proteins from the target species. These investigations showed that B. subtilis had a higher affinity for binding. These findings were further validated by molecular dynamic simulations. The synthesised chemical was subjected to in silico toxicity assessment using seven models, which demonstrated its non-irritating properties on the skin and eyes. The extensive analysis that is given here lays the groundwork for more targeted research on novel antibacterial drugs, with a particular focus on the safety, molecular interactions, and effectiveness of these compounds. As a result of the compound's potential applicability in biocompatible antimicrobial formulations, it is a viable candidate for improving the development of antibacterial medicines that are both effective and safe. [Display omitted]