Theoretical insights into solvent-polarity-associated excited state behaviors for a novel 2-hydroxy-1-naphthaldehyde-triphenylamine (TPHY) fluorophore: A TDDFT study

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Accounts of Chemical Research Pub Date : 2024-06-21 DOI:10.1002/jccs.202400072

Mengmeng Hou, Meiyi Zhang, Jinfeng Zhao, Liang Yang, Zhe Tang

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Abstract

Inspired by the profound allure of the exquisitely regulated characteristics exhibited by 2-hydroxy-1-naphthaldehyde-triphenylamine (TPHY) and its derivatives in the realms of photochemistry and photophysics, our current endeavor primarily revolves around delving into the intricacies of photo-induced excited state reactions for TPHY fluorophores within solvents boasting varying degrees of polarity. Our simulations, resulting from variations in geometry and vertical excitation charge reorganization, unveil solvent polarity-dependent hydrogen bonding interactions and charge recombination induced by photoexcitation that can significantly enhance the excited state intramolecular proton transfer (ESIPT) reaction for TPHY chemosensor. By constructing potential energy surfaces (PESs), we reveal that the single ESIPT reaction of TPHY occurs concurrently with alternative dual intramolecular hydrogen bonds (O1-H2···N3 and O4-H5···N6). We sincerely hope that the regulation of solvent polarity on excited state behaviors may pave the way for the development of innovative luminescent materials.

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新型 2-hydroxy-1-naphthaldehyde-triphenylamine (TPHY) 荧光团溶剂-极性相关激发态行为的理论见解：TDDFT 研究

受 2-hydroxy-1-naphthaldehyde-triphenylamine (TPHY) 及其衍生物在光化学和光物理领域所表现出的精细调节特性的深刻诱惑，我们目前的工作主要围绕深入研究 TPHY 荧光团在不同极性溶剂中的光诱导激发态反应的复杂性。通过对几何形状和垂直激发电荷重组的变化进行模拟，我们揭示了光激发诱导的依赖于溶剂极性的氢键相互作用和电荷重组，这可以显著增强 TPHY 化学传感器的激发态分子内质子转移（ESIPT）反应。通过构建势能面（PES），我们发现 TPHY 的单一 ESIPT 反应与替代性双分子内氢键（O1-H2--N3 和 O4-H5--N6）同时发生。我们衷心希望溶剂极性对激发态行为的调控能为创新发光材料的开发铺平道路。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.