2-Thiopyridone-based stilbazoles: Synthesis, photo-physical properties and sensing of Hg(II) and Cd(II) ions

IF 4.1 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2024-11-10 DOI:10.1016/j.dyepig.2024.112538

Anastasia I. Ershova, Ilzia I. Khakimova, Mikhail Yu. Ievlev, Oleg V. Ershov

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Abstract

A method of preparation of new representatives of donor-acceptor stilbazoles based on pyridine-2-thione containing a cyano group and a trifluoromethyl moiety in the acceptor part of the molecule was developed. The synthesized stilbazoles exhibited pronounced fluorescence, with quantum yields up to about 15 % significantly improved compared to traditional thioxonicotinonitriles, which typically lack such properties. The emission turned out to be strongly dependent on the tautomeric equlibrium in the solution that was studied using both computational methods and comprehensive spectroscopic analysis. Solvato(fluoro)chromism and the influence of the substituent on the spectral characteristics of the compounds were also investigated. It was established that the emission maximum could be tuned from 418 to 630 nm covering almost the entire visible spectrum. The design of stilbazoles enhanced their photophysical properties making them suitable candidates for environmental monitoring or biological sensing. As a result a new chemosensor was developed demonstrating high selectivity for the detection of micromolar concentration of mercury(II) ions (LoD 1.34 μM) and submicromolar concentration of cadmium(II) ions (LoD 0.875 μM) in aqueous media.

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2-Thiopyridone-based stilbazoles：合成、光物理性质以及对 Hg(II) 和 Cd(II) 离子的传感

本研究开发了一种基于吡啶-2-硫酮的供体-受体链烷唑新代表的制备方法，该吡啶-2-硫酮在分子的受体部分含有一个氰基和一个三氟甲基。合成的苯并唑具有明显的荧光，量子产率高达约 15%，与通常缺乏此类特性的传统硫酮腈相比有显著提高。通过计算方法和综合光谱分析研究发现，发射与溶液中的同分异构体平衡密切相关。此外，还研究了溶解（氟）发色性以及取代基对化合物光谱特性的影响。结果表明，发射最大值可在 418 至 630 纳米之间调节，几乎覆盖了整个可见光谱。苯并唑的设计增强了其光物理性质，使其成为环境监测或生物传感的合适候选化合物。因此，我们开发出了一种新型化学传感器，对检测水介质中微摩尔浓度的汞（II）离子（LoD 1.34 μM）和亚摩尔浓度的镉（II）离子（LoD 0.875 μM）具有很高的选择性。

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来源期刊

Dyes and Pigments 工程技术-材料科学：纺织

CiteScore

8.20

自引率

13.30%

发文量

933

审稿时长

33 days

期刊介绍： Dyes and Pigments covers the scientific and technical aspects of the chemistry and physics of dyes, pigments and their intermediates. Emphasis is placed on the properties of the colouring matters themselves rather than on their applications or the system in which they may be applied. Thus the journal accepts research and review papers on the synthesis of dyes, pigments and intermediates, their physical or chemical properties, e.g. spectroscopic, surface, solution or solid state characteristics, the physical aspects of their preparation, e.g. precipitation, nucleation and growth, crystal formation, liquid crystalline characteristics, their photochemical, ecological or biological properties and the relationship between colour and chemical constitution. However, papers are considered which deal with the more fundamental aspects of colourant application and of the interactions of colourants with substrates or media. The journal will interest a wide variety of workers in a range of disciplines whose work involves dyes, pigments and their intermediates, and provides a platform for investigators with common interests but diverse fields of activity such as cosmetics, reprographics, dye and pigment synthesis, medical research, polymers, etc.