Exploring Dual Solvatochromic Traits in Novel Fluorescent Benzanthrone Ethynyl Derivatives

IF 1.4 4区化学 Q4 CHEMISTRY, PHYSICAL

Journal of Solution Chemistry Pub Date : 2024-03-05 DOI:10.1007/s10953-024-01363-x

Armands Maļeckis, Marija Cvetinska, Evans Griškjāns, Elena Kirilova

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Abstract

Motivated by the scarcity of prior research, in this study we report the synthesis and photophysical characteristics of newly obtained benzanthrone ethynyl derivatives. Fourier-transform infrared spectroscopy, ¹H and ¹³C nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry elucidated the structures of the compounds. To study photophysical characteristics, absorbance and emission spectra were measured in solvents with different polarities. Photofading proved high stability of the synthesized compounds (up to 96% of initial absorption after irradiation for 4 h). The analyzed compounds are fluorescent (quantum yields from 0.01 to 0.74 in ethanol) with a significant solvatochromic effect (from 466 nm in benzene to 720 nm in dimethyl sulfoxide). Based on these findings, there is a correlation between the electronic nature of substituents and photophysical parameters. Hence, these compounds could find applications as probes in fluorescence microscopy and sensors to detect polarity variations.

Graphical Abstract

Abstract Image

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探索新型荧光苯并蒽酮乙炔基衍生物的双重溶解变色特性

由于之前的研究很少，我们在本研究中报告了新获得的苯并蒽酮乙炔基衍生物的合成和光物理特性。傅立叶变换红外光谱、1H 和 13C 核磁共振谱以及高分辨质谱阐明了这些化合物的结构。为了研究光物理特性，在不同极性的溶剂中测量了吸光度和发射光谱。光衰减证明了合成化合物的高稳定性（照射 4 小时后可达到初始吸收量的 96%）。所分析的化合物具有荧光特性（在乙醇中的量子产率从 0.01 到 0.74），并具有显著的溶解变色效应（在苯中的波长从 466 纳米到二甲亚砜中的 720 纳米）。基于这些发现，取代基的电子性质与光物理参数之间存在相关性。因此，这些化合物可用作荧光显微镜的探针和检测极性变化的传感器。

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来源期刊

Journal of Solution Chemistry 化学-物理化学

CiteScore

2.30

自引率

0.00%

发文量

审稿时长

3-8 weeks

期刊介绍： Journal of Solution Chemistry offers a forum for research on the physical chemistry of liquid solutions in such fields as physical chemistry, chemical physics, molecular biology, statistical mechanics, biochemistry, and biophysics. The emphasis is on papers in which the solvent plays a dominant rather than incidental role. Featured topics include experimental investigations of the dielectric, spectroscopic, thermodynamic, transport, or relaxation properties of both electrolytes and nonelectrolytes in liquid solutions.