2ʹ-苄氧基黄酮的合成与荧光特性--用于选择性检测苦味酸和 pH 值传感的双重探针

IF 3.5 Q2 CHEMISTRY, ANALYTICAL
Vengatesh Gopal, Jayasankar Sudhakaran, Nirenjana Ramachandran, Thejus Kozhiyottu Mana, Aravind Remesh Kana, Anandhu Omanakuttan Nair, Priyanka Mohan, Tejaswini Madhusudhan, Sankarasekaran Shanmugaraju and Pandurangan Nanjan
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引用次数: 0

摘要

黄酮类化合物是天然存在的含氧杂环系统,具有独特的性能,可用于多种用途。本研究报告了一种新的 2ʹ-苄氧基黄酮的合成,并探讨了其对二次化学爆炸物苦味酸和 pH 值传感的荧光传感特性。目标 2ʹ-苄氧基黄酮荧光团(5)通过三步反应合成,收率良好,并利用核磁共振、傅立叶变换红外光谱和 HRMS 对其进行了全面表征。利用荧光光谱探测了 5 对硝基芳烃和 pH 值的感应倾向。化合物 5 对酚类硝基芳香族化合物具有优先感应特性,对苦味酸具有较高的淬灭效率,并且在不同 pH 值下具有不同的荧光反应。5 号化合物对苦味酸的卓越选择性归因于 5 号化合物中的 O 原子与苦味酸的 OH 基团之间的分子间氢键相互作用。计算结果进一步验证了观察到的实验结果,并有力地支持了氢键驱动的传感选择性。此外,在实际水样中和使用纸质传感技术时,进一步证明了 5 对苦味酸的选择性传感。这些研究使化合物 5 成为一种潜在的双重传感器,既能选择性地感知苦味酸,又能感知介质的 pH 值。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis and fluorescence properties of 2′-benzyloxy flavone—a dual probe for selective detection of picric acid and pH sensing†

Synthesis and fluorescence properties of 2′-benzyloxy flavone—a dual probe for selective detection of picric acid and pH sensing†

Flavonoids are naturally occurring oxygen-containing heterocyclic systems with unique properties for diverse applications. The present study reports the synthesis of a new 2′-benzyloxy flavone and explores its fluorescence sensing properties towards secondary chemical explosives, such as picric acid, and pH sensing. The target 2′-benzyloxy flavone fluorophore (5) was synthesized in three-step reactions with good yield and was fully characterized using NMR, FTIR spectroscopy, and HRMS. The sensing propensity of 5 towards nitroaromatics and pH was probed using fluorescence spectroscopy. Compound 5 exhibited a preferential sensing property for phenolic nitroaromatics with high quenching efficiency for picric acid and differential fluorescence responses for different pH. The superior selectivity of 5 for picric acid is attributed to the intermolecular hydrogen bonding interactions between the O atoms in 5 and the OH groups of picric acid. The observed experimental results were further validated by computational calculations which strongly supported the hydrogen-bond-driven sensing selectivity. Furthermore, selective sensing of picric acid by 5 was further demonstrated in real-water samples and using paper-based sensing. These studies make compound 5 a potential dual sensor for selective sensing of picric acid and sensing of pH of the medium.

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