计算化学促进了第二种近红外氧杂蒽基染料的开发。

IF 2.1 4区 化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Journal of Molecular Modeling Pub Date : 2024-10-29 DOI:10.1007/s00894-024-06179-6
Qinlin Yuan, Mingyu Wang, Mingyue Ma, Pingping Sun, Chaoyuan Zeng, Weijie Chi
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引用次数: 0

摘要

背景:第二近红外(NIR-II)区的染料在成像技术的发展中起着至关重要的作用。然而,由于缺乏合理的设计策略,开发 NIR-II 小分子染料在满足生物领域的大量需求方面遇到了重大瓶颈。在此,我们通过用-C(CH3)2、-Si(CH3)2、-SO2和-P(O)Ph取代香蒽基染料中的氧桥原子,设计了一系列具有更多红移发射的罗丹明类似物。我们利用(随时间变化的)密度泛函理论研究了香蒽基染料的前沿分子轨道、静电位面、相互作用区指标、电子-空穴分布以及吸收和发射光谱。我们的研究结果表明,这些设计的小分子染料具有 1377-1809 纳米的长发射波长。我们希望这些发现能使我们有针对性地设计出长波长的罗丹明:方法:使用 Gaussian 16 A03 在 ω-B97XD/Def2SVP 水平上对染料的基态和激发态进行了几何优化。吸收和发射波长用 13 个函数进行了评估,包括 TPSSH、O3LYP、B3LYP*、B3LYP、PBE0、MPW1B95、PBE-1/3、PBE38、MPWB1K、MN15、BHandHLYP、ω-B97XD 和 CAM-B3LYP。
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Computational chemistry facilitates the development of second near-infrared xanthene-based dyes

Context

The dyes in the second near-infrared (NIR-II) region play a crucial role in advancing imaging technology. However, developing small-molecule dyes in NIR-II poses a significant bottleneck to meet the substantial demands in biological fields, which may be attributed to the lack of a rational design strategy. Herein, we designed a series of rhodamine analogs with more red-shifted emission by replacing the oxygen-bridge atom in xanthene-based dyes with –C(CH3)2, –Si(CH3)2, –SO2, and –P(O)Ph. We investigated the frontier molecular orbital, electrostatic potential surfaces, the interaction region indicator, electron–hole distribution, and absorption and emission spectrum of xanthene-based dyes using (time-dependent) density functional theory. Our results demonstrated that these designed small molecular dyes exhibit long emission wavelengths covering 1377–1809 nm. We expected these findings to enable the targeted design of long-wavelength rhodamines.

Method

Geometry optimization of dyes in the ground and excited states was carried out at ω-B97XD/Def2SVP level using Gaussian 16 A03. The absorption and emission wavelengths were evaluated using 13 functional, including TPSSH, O3LYP, B3LYP*, B3LYP, PBE0, MPW1B95, PBE-1/3, PBE38, MPWB1K, MN15, BHandHLYP, ω-B97XD, and CAM-B3LYP.

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来源期刊
Journal of Molecular Modeling
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.
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