Theoretical Study on the Effect of Cyano- and Dimethylamine-Group on ESIPT Behavior and Luminescent Properties of Novel Flavone-Based Fluorophore.

IF 2.6 4区化学 Q2 BIOCHEMICAL RESEARCH METHODS

Journal of Fluorescence Pub Date : 2024-08-21 DOI:10.1007/s10895-024-03914-3

Zhengyi Zhang, Hua Fang

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Abstract

Recently, a new fluorescent senor based on 3-hydroxy-2-(naphthalen-2-yl)-4 H-chromen-4-one (HFN) for selective detection of H₂S_n was obtained in the experiment (Spectrochim. Acta Part A 271(2022)120962). Based on HFN, three new compounds (HFN1, HFN2 and HFN3) are designed to explore the influences of dimethylamine (-N(CH₃)₂) and cyano (-CN) groups on the excited-state intramolecular proton transfer (ESIPT) process and luminescent features of HFN. After analyzing the mainly geometrical parameters, electron densities and infrared spectra, we discovered that the intramolecular hydrogen bonds (IHBs) in the target molecules become stronger upon photo-excitation. Introducing -CN or/and -N(CH₃)₂ groups into HFN indeed influences its ESIPT behavior and luminescent properties. The -N(CH₃)₂ group enhances IHB, reduces ESIPT barrier and caused absorption/ fluorescence (at T form) peak blue-shift, while the -CN group shows a counterproductive effect. The coincidence of -N(CH₃)₂ and -CN made the absorption/fluorescent wavelength of HFN red-shift more than single -N(CH₃)₂ or -CN group does.

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氰基和二甲胺基团对新型黄酮基荧光团 ESIPT 行为和发光特性影响的理论研究。

最近，一种基于 3-羟基-2-(萘-2-基)-4 H-色烯-4-酮（HFN）的新型荧光感应器在实验中获得，可用于选择性检测 H2Sn（Spectrochim.Acta Part A 271(2022)120962）。在 HFN 的基础上，设计了三个新化合物（HFN1、HFN2 和 HFN3），以探索二甲基胺（-N(CH3)2）和氰基（-CN）对 HFN 激发态分子内质子转移过程和发光特征的影响。在分析了主要的几何参数、电子密度和红外光谱后，我们发现目标分子中的分子内氢键（IHBs）在光激发时会变得更强。在 HFN 中引入-CN 或/和-N(CH3)2 基团确实会影响其 ESIPT 行为和发光特性。-N(CH3)2基团增强了IHB，降低了ESIPT势垒，并导致吸收/荧光（在T形态）峰蓝移，而-CN基团则显示出反作用。与单个-N(CH3)2 或-CN 基团相比，-N(CH3)2 和-CN 的同时存在会使 HFN 的吸收/荧光波长发生更多的红移。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Fluorescence 化学-分析化学

CiteScore

4.60

自引率

7.40%

发文量

203

审稿时长

5.4 months

期刊介绍： Journal of Fluorescence is an international forum for the publication of peer-reviewed original articles that advance the practice of this established spectroscopic technique. Topics covered include advances in theory/and or data analysis, studies of the photophysics of aromatic molecules, solvent, and environmental effects, development of stationary or time-resolved measurements, advances in fluorescence microscopy, imaging, photobleaching/recovery measurements, and/or phosphorescence for studies of cell biology, chemical biology and the advanced uses of fluorescence in flow cytometry/analysis, immunology, high throughput screening/drug discovery, DNA sequencing/arrays, genomics and proteomics. Typical applications might include studies of macromolecular dynamics and conformation, intracellular chemistry, and gene expression. The journal also publishes papers that describe the synthesis and characterization of new fluorophores, particularly those displaying unique sensitivities and/or optical properties. In addition to original articles, the Journal also publishes reviews, rapid communications, short communications, letters to the editor, topical news articles, and technical and design notes.

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