Tetraphenylethylene-connected monoquaternized 4-(4-pyridyl)pyridinium: A colorimetric probe for detecting trace amounts of water in organic solvents

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED

Dyes and Pigments Pub Date : 2025-05-31 DOI:10.1016/j.dyepig.2025.112926

Karolin P. Jose , R. Rameshbabu Priyadharsan , Kamalanathan Chidambaranathan , Subramanian Karthikeyan , Savarimuthu Philip Anthony , Vedichi Madhu

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引用次数: 0

Abstract

Tetraphenylethylene (TPE) and triphenylamine (TPA) electron donor attached mono-quaternized 4-(4-pyridyl)pyridinium derivatives, (1-(2-oxo-2-(4-(1,2,2-triphenylvinyl)phenyl)ethyl)-[4,4′-bipyridin]-1-ium bromide (TPE-MQ) and 1-(2-(4-(diphenylamino)phenyl)-2-oxoethyl)-[4,4′-bipyridin]-1-ium bromide (TPA-MQ) were synthesized and investigated the role of TPE/TPA in tuning their optical properties. Both TPE-MQ and TPA-MQ showed strong intramolecular charge transfer (ICT), which was confirmed through HOMO/LUMO calculations and solvent polarity dependent absorption studies. Interestingly, the acidic methylene of TPE-MQ was found to be highly sensitive to water compared to TPA-MQ. Even trace amounts of water in organic solvents acted as nucleophiles, leading to keto-enol formation and intense color due to enhanced π-conjugation. In contrast, TPA-MQ did not display any color or absorption changes in the presence of water. The water-induced structural conversion from keto to enol form was confirmed using ¹H NMR analysis. Further, TPE-MQ colorimetric probe displayed clear color changes in presence of trace amounts of water in polar protic, aprotic, and non-polar solvents. Thus, the present study developed a simple naked-dye detecting colorimetric probe for sensing trace amount of water in organic solvents including commercial solvents.

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四苯乙烯连接单季铵化4-（4-吡啶基）吡啶：用于检测有机溶剂中痕量水的比色探针

合成了四苯基乙烯（TPE）和三苯基胺（TPA）电子供体连接的单季铵化4-（4-吡啶基）吡啶衍生物（1-（2-氧-2-（1,2,2-三苯基乙烯）苯基）乙基）-[4,4 ' -联吡啶]-1-溴化ium （TPA- mq）和1-（2-（4-（二苯基）苯基）-2-氧乙基）-[4,4 ' -联吡啶]-1-溴化ium (TPA- mq)，并研究了TPE/TPA对其光学性质的调节作用。TPE-MQ和TPA-MQ均表现出很强的分子内电荷转移（ICT），通过HOMO/LUMO计算和溶剂极性依赖吸收研究证实了这一点。有趣的是，与TPA-MQ相比，TPE-MQ的酸性亚甲基对水非常敏感。在有机溶剂中，甚至微量的水作为亲核试剂，导致酮烯醇的形成和强烈的颜色，因为π共轭增强。相比之下，TPA-MQ在存在水的情况下没有显示任何颜色或吸收变化。通过1H NMR分析证实了水诱导的酮到烯醇的结构转化。此外，TPE-MQ比色探针在极性质子、非质子和非极性溶剂中存在微量水时显示出明显的颜色变化。因此，本研究开发了一种简单的裸染料检测比色探针，用于检测有机溶剂（包括商业溶剂）中的痕量水。

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

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.