Synthesis, characterization, optical properties, biological activity and theoretical studies of a 4 nitrobenzylidene) amino) phenyl)imino)methyl)naphthalen-2-ol -based fluorescent Schiff base
Sadeq M. AlHazmy,
Mohamed Oussama Zouaghi,
Ahmed N. Al-Hakimi,
Thamer Alorini,
Ibrahim A. Alhagri,
Youssef Arfaoui,
Rania Al-Ashwal,
Lamjed Mansour,
Naceur Hamdi
Affiliations
Sadeq M. AlHazmy
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia
Mohamed Oussama Zouaghi
Laboratory of Characterizations, Applications & Modeling of Materials (LR18ES08), Department of Chemistry, Faculty of Sciences, University of Tunis El Manar, 2092, Tunis, Tunisia
Ahmed N. Al-Hakimi
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia
Thamer Alorini
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia
Ibrahim A. Alhagri
Department of Chemistry, College of Science, Qassim University, Buraidah, 51452, Saudi Arabia
Youssef Arfaoui
Laboratory of Characterizations, Applications & Modeling of Materials (LR18ES08), Department of Chemistry, Faculty of Sciences, University of Tunis El Manar, 2092, Tunis, Tunisia
Rania Al-Ashwal
School of Biomedical Engineering and Health Sciences, Faculty of Engineering, Universiti Teknologi Malaysia, Johor Bahru, 81310, Malaysia; Advanced Diagnostic and Progressive Human Care Research Group, School of Biomedical Engineering and Health Science Teknologi Malaysia, Johor Bahru, 81310, Malaysia
Lamjed Mansour
Zoology Department, College of Science, King Saud University, Saudi Arabia, P.O. Box 2455, Riyadh, 11451, Saudi Arabia
Naceur Hamdi
Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif, Tunisia; Corresponding author.
A new Schiff base, 1-(E)-(4-((E) 4nitrobenzylidene) amino) phenyl)imino) methyl)naphthalen-2-ol (4NMN), was prepared from the reaction of p-phenylenediamine with 2-hydroxy-1-naphthaldehyde and 4-nitrobenzaldehyde and characterized with spectroscopic analysis. UV-VIS and NMR. Frontier molecular orbitals, molecular electrostatic potential, and chemical reactivity descriptors of the synthesized compound were studied using molecular modeling methods. The antibacterial and antifungal activities of the Schiff base were studied for its minimum inhibitory concentration. The compound showed a higher effect on yeast than against bacteria. Density functional theory (DFT) calculations were performed to study the mechanism of reaction for the synthesis of 4NMN, and the results were consistent with the experimental findings. 4NMN exhibited moderate antibacterial and antifungal activities and demonstrated higher inhibition potential against different resistant strains compared to the reference drug gentamycin. The absorption and fluorescence spectra of 4NMN were measured in different solvents, and the effect of relative polarity and acidity on the medium was observed. An inner filter effect was observed at high concentrations, and the compound showed considerable fluorescence enhancement with increasing medium viscosity and fluorescence quenching by the addition of traces of Cr1+ and Cu2+. Additionally, molecular docking studies were conducted to investigate the efficiency of antibacterial and antifungal targets.
