Bis-tetraarylimidazole macrocycle: An effective fluorescent sensor for folic acid

IF 4.2 3区工程技术 Q2 CHEMISTRY, APPLIED Dyes and Pigments Pub Date : 2025-02-08 DOI:10.1016/j.dyepig.2025.112691

Ling Zheng , Xinyao Chen , Liangbin Lin , Hongyu Guo , Fafu Yang

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Abstract

Folic acid (FA) is an essential vitamin. The development of rapid, simple and on-site detecting method on FA is of great importance to human's health and industrial production. In this work, a bis-tetraarylimidazole macrocycle (BTM) was designed and synthesized as an effective fluorescent sensor for FA. The weak purple fluorescence of BTM was transferred to strong blue fluorescence after sensing FA with high sensing selectivity among 31 kinds of biomolecules and 16 kinds of ions. The limit of detection was as low as 1.06 × 10⁻⁷ M, which was the competitive one among the reported fluorescence sensors. The sensing mechanism was deduced that FA was included in the cavity of BTM based on the multiple hydrogen-bonding actions and aromatic π-π stacking interaction. The intermolecular rotating restriction and the interruption of Dexter electron transfer after binding FA were responsible for the fluorescence enhancement. This sensing ability of BTM for FA was applied on test paper, seal experiment and stimulated samples, suggesting the good qualitative and quantitative detecting ability for FA with rapid, simple and on-site procedure in real environment.

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双-四芳基咪唑大环：叶酸的有效荧光传感器

叶酸（FA）是一种必需的维生素。开发快速、简便的FA现场检测方法对人类健康和工业生产具有重要意义。本文设计并合成了一种双四芳基咪唑大环（BTM）作为FA的有效荧光传感器。BTM对31种生物分子和16种离子具有高选择性的感应FA后，弱紫色荧光转变为强蓝色荧光。该荧光传感器的检出限低至1.06 × 10−7 M，在已有的荧光传感器中具有较强的竞争力。基于多重氢键作用和芳香族π-π堆积相互作用，推断出FA被包含在BTM空腔中的传感机理。分子间的旋转限制和结合FA后Dexter电子转移的中断是荧光增强的原因。将BTM对FA的检测能力应用于试纸、密封实验和模拟样品上，表明BTM对FA具有良好的定性和定量检测能力，在实际环境中具有快速、简单、现场的检测方法。

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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.