Effect of Solvent on Donor and Acceptor Schiff Base of (E)-5-(diethylamino)-2-(4-nitrophenyl)methyl Phenol: Photophysical, Theoretical, Molecular Docking Studies, and Biological Applications

IF 3.9 3区化学 Q2 POLYMER SCIENCE

Journal of Inorganic and Organometallic Polymers and Materials Pub Date : 2024-08-13 DOI:10.1007/s10904-024-03289-9

V. Rosi, S. Munusamy, P. Karunakaran, K. Rajesh, T. Bavani, Tahani Mazyad Almutairi

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Abstract

The photophysical properties of the donor N,N-diethylamino (-NEt₂) and acceptor nitro (-NO₂) group substituted salicylideneaniline derivative (E)-5-(diethylamino)-2-(4-nitrophenyl)methylphenol (DSAN), were investigated using steady-state and time-resolved fluorescence spectroscopy. Different solvents showed intramolecular charge transfer (ICT) and excited-state intramolecular proton transfer (ESIPT) states. The pH effect on DSAN revealed enol, ICT, ESIPT states, and anionic forms. Solute–solvent interactions, like hydrogen bonding, influenced longer wavelength emissions in high-polarity solvents, indicating the ICT state. DFT studies optimized the DSAN molecule in various solvents, and electrostatic potential analysis identified electrophilic and nucleophilic areas and the HOMO–LUMO band energy gap was around 3.0 eV. Also the molecular docking studies showed DSAN's hydrophobic and hydrogen bond interactions with thymidylate synthase (TS). Biological studies indicated DSAN has minimal antioxidant and antimicrobial activity.

Graphical Abstract

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溶剂对(E)-5-(二乙基氨基)-2-(4-硝基苯基)甲基苯酚的施主和受主希夫碱的影响：光物理、理论、分子对接研究和生物应用

采用稳态和时间分辨荧光光谱法研究了供体 N,N-二乙基氨基（-NEt2）和受体硝基（-NO2）取代的水杨酸苯胺衍生物 (E)-5-(diethylamino)-2-(4-nitrophenyl)methylphenol (DSAN) 的光物理特性。不同溶剂显示出分子内电荷转移（ICT）和激发态分子内质子转移（ESIPT）状态。pH 对 DSAN 的影响显示了烯醇态、ICT 态、ESIPT 态和阴离子态。在高极性溶剂中，溶质与溶剂的相互作用（如氢键）会影响较长波长的发射，从而显示出 ICT 状态。DFT 研究对各种溶剂中的 DSAN 分子进行了优化，静电位分析确定了亲电和亲核区域，HOMO-LUMO 带能隙约为 3.0 eV。分子对接研究还表明，DSAN 与胸腺嘧啶酸合成酶（TS）存在疏水和氢键相互作用。生物学研究表明，DSAN 具有极低的抗氧化和抗菌活性。

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来源期刊

Journal of Inorganic and Organometallic Polymers and Materials 化学-高分子科学

CiteScore

8.30

自引率

7.50%

发文量

335

审稿时长

1.8 months

期刊介绍： Journal of Inorganic and Organometallic Polymers and Materials [JIOP or JIOPM] is a comprehensive resource for reports on the latest theoretical and experimental research. This bimonthly journal encompasses a broad range of synthetic and natural substances which contain main group, transition, and inner transition elements. The publication includes fully peer-reviewed original papers and shorter communications, as well as topical review papers that address the synthesis, characterization, evaluation, and phenomena of inorganic and organometallic polymers, materials, and supramolecular systems.