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IF 2.1 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Molecular Modeling Pub Date : 2025-03-17 DOI:10.1007/s00894-025-06343-6

Jiaoni Pan, Jinfeng Zhao, Jiahe Chen

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引用次数: 0

摘要

背景本研究采用TDDFT方法，主要探讨了卤素取代的2,5-双(4,5-二苯基-1H-咪唑-2-基)苯-1,4-二醇（BDIBD）衍生物（即BDIBD-FF、BDIBD-FCl和BDIBD-FBr）的光诱导激发态双氢键相互作用。通过对化学键性质、键长和键角、红外光谱位移以及模拟的核价分叉（CVB）参数进行分析，我们发现 BDIBD-FF、BDIBD-FCl 和 BDIBD-FBr 在 S1 态受到激发后，双氢键得到了加强。光诱导电荷的变化进一步揭示了激发态分子内双质子转移（ESIDPT）的趋势。通过构建势能面（PES），我们不仅阐明了 BDIBD 衍生物的分步 ESIDPT 机制，还呈现了卤素元素调控的 ESIDPT 行为。方法基于高斯 16 程序，使用 DFT 和 TDDFT 方法对所有 BDIBD 衍生物进行了 D3-B3LYP 和 TZVP 理论水平的优化。通过比较几何结构的变化，并利用 Multiwfn 3.8 探索预测氢键强度的核价分岔指数，分析了双氢键相互作用。探索了具有过渡态形式的势能面，从而揭示了 ESIDPT 机制。

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Theoretical investigation of dual hydrogen-bonding interactions and ESIDPT mechanism associated with halogen substituted 2,5-bis(4,5-diphenyl-1H-imidazol-2-yl)benzene-1,4-diol derivatives

Context

In this work, using the TDDFT method, we mainly focus on exploring the photo-induced excited state dual hydrogen-bonding interactions for halogen element substituted 2,5-bis(4,5-diphenyl-1H-imidazol-2-yl)benzene-1,4-diol (BDIBD) derivatives (i.e., BDIBD-FF, BDIBD-FCl and BDIBD-FBr). Analyses of chemical bond properties, bond lengths and bond angles, infrared (IR) spectral shifts, as well as the simulated core-valence bifurcation (CVB) parameters, we find upon excitation dual hydrogen bonds of BDIBD-FF, BDIBD-FCl, and BDIBD-FBr are strengthened in the S₁ state. Variations about photo-induced charge further reveal the excited state intramolecular double proton transfer (ESIDPT) tendency. By constructing potential energy surfaces (PESs), we not only clarify the stepwise ESIDPT mechanism for BDIBD derivatives, but also present the halogen element regulated ESIDPT behaviors.

Methods

Based on Gaussian 16 program, all BDIBD derivatives were optimized using DFT and TDDFT methods with D3-B3LYP and TZVP theoretical levels. By comparing geometries variations and exploring core-valence bifurcation indexes for predicting hydrogen-bonding strength using Multiwfn 3.8, dual hydrogen-bonding interactions were analyzed. Potential energy surfaces with transition state forms were explored to reveal the ESIDPT mechanism.

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来源期刊

Journal of Molecular Modeling 化学-化学综合

CiteScore

3.50

自引率

4.50%

发文量

362

审稿时长

2.9 months

期刊介绍： The Journal of Molecular Modeling focuses on "hardcore" modeling, publishing high-quality research and reports. Founded in 1995 as a purely electronic journal, it has adapted its format to include a full-color print edition, and adjusted its aims and scope fit the fast-changing field of molecular modeling, with a particular focus on three-dimensional modeling. Today, the journal covers all aspects of molecular modeling including life science modeling; materials modeling; new methods; and computational chemistry. Topics include computer-aided molecular design; rational drug design, de novo ligand design, receptor modeling and docking; cheminformatics, data analysis, visualization and mining; computational medicinal chemistry; homology modeling; simulation of peptides, DNA and other biopolymers; quantitative structure-activity relationships (QSAR) and ADME-modeling; modeling of biological reaction mechanisms; and combined experimental and computational studies in which calculations play a major role.