基于香豆素衍生物在水溶液中检测CN-的高灵敏性双通道化学传感器及其在食品样品中的应用

doi:10.6023/cjoc201909037

有机化学 ›› 2020, Vol. 40 ›› Issue (5): 1232-1238.DOI: 10.6023/cjoc201909037 上一篇下一篇

研究论文

基于香豆素衍生物在水溶液中检测CN^-的高灵敏性双通道化学传感器及其在食品样品中的应用

付青青, 胡京汉, 姚瑛, 殷志远, 贵铠, 龙辰, 倪朋伟

兰州交通大学化学与生物工程学院兰州 730070

收稿日期:2019-09-26 修回日期:2019-11-18 发布日期:2020-01-15
通讯作者: 胡京汉 E-mail:hujinghan62@163.com
基金资助:
国家自然科学基金（No.21467012）资助项目.

Novel High Sensitivity Dual-Channel Chemosensor for Detecting CN^- Based on Coumarin Derivative in Aqueous Media and Its Application in Food Samples

Fu Qingqing, Hu Jinghan, Yao Ying, Yin Zhiyuan, Gui Kui, Long Chen, Ni Pengwei

College of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070

Received:2019-09-26 Revised:2019-11-18 Published:2020-01-15
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21467012).

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摘要/Abstract

设计并合成了一种基于3，4，5-三羟基苯甲酰肼和4-甲基-7-羟基-8-醛基香豆素的简单传感器FQ，该传感器在水性介质中对氰化物具有“开启”的荧光响应.传感器FQ的羟基和酚羟基是识别基团，香豆素起信号报告的作用.传感器FQ上的吸电子基团（羟基）阻止了与香豆素基团之间的分子内电荷转移.当添加氰根时，可通过两步去质子化作用去掉酰肼上的质子和羟基上的质子，从而苯基和香豆素基团之间的分子内电荷转移（ICT）可以正常进行.通过¹H NMR滴定和量化计算（DFT）证实了逐步去质子化的机理.此外，传感器FQ对氰根的荧光响应的检测极限相对较低（9.92×10^-8 mol·L^-1）.值得注意的是，传感器FQ已成功用于检测食品样品中的氰化物阴离子，而且制备了基于FQ的检测试纸，该试纸可以方便快捷地检测水中的氰根.

关键词: CN^-, 比色, 分步去质子, 试纸条, DFT

Based on 3,4,5-trihydroxybenzohydrazide and 4-methyl-7-hydroxy-8-aldehyde coumarin, a simple sensor FQ was designed and synthesized, which showed the "turn-on" fluorescence response to cyanide in an aqueous medium. The hydrazide, hydroxyl and phenolic hydroxyl groups on FQ were receptor unit, and coumarin plays a role in signal reporting. The electron withdrawing group (hydroxyl group) of FQ prevented its intramolecular charge transfer with coumarin group. When CN^- was added, the protons of hydrazide and hydroxyl group were removed by protonation in two-step, so that intramolecular charge transfer (ICT) between phenyl group and coumarin group could be carried out. The mechanism of step-by-step deprotonation was confirmed by ¹H NMR titration and DFT calculation. Furthermore, compared to the reported literature, FQ had a lower detection line for CN^- fluorescence detection (9.92×10^-8 mol·L^-1). Notably sensor FQ has been successfully used to detect cyanide anions in food samples. The prepared FQ-containing test strip could be used colorimetric device for CN^- detection.

Key words: CN^-, colorimetric, deprotonation, test strip, DFT

引用此文

付青青, 胡京汉, 姚瑛, 殷志远, 贵铠, 龙辰, 倪朋伟. 基于香豆素衍生物在水溶液中检测CN^-的高灵敏性双通道化学传感器及其在食品样品中的应用[J]. 有机化学, 2020, 40(5): 1232-1238.

Fu Qingqing, Hu Jinghan, Yao Ying, Yin Zhiyuan, Gui Kui, Long Chen, Ni Pengwei. Novel High Sensitivity Dual-Channel Chemosensor for Detecting CN^- Based on Coumarin Derivative in Aqueous Media and Its Application in Food Samples[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1232-1238.

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基于香豆素衍生物在水溶液中检测CN^-的高灵敏性双通道化学传感器及其在食品样品中的应用

Novel High Sensitivity Dual-Channel Chemosensor for Detecting CN^- Based on Coumarin Derivative in Aqueous Media and Its Application in Food Samples

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基于香豆素衍生物在水溶液中检测CN-的高灵敏性双通道化学传感器及其在食品样品中的应用

Novel High Sensitivity Dual-Channel Chemosensor for Detecting CN- Based on Coumarin Derivative in Aqueous Media and Its Application in Food Samples

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基于香豆素衍生物在水溶液中检测CN^-的高灵敏性双通道化学传感器及其在食品样品中的应用

Novel High Sensitivity Dual-Channel Chemosensor for Detecting CN^- Based on Coumarin Derivative in Aqueous Media and Its Application in Food Samples