基于香豆素衍生物反应型识别CN-的紫外荧光传感器及其应用研究

doi:10.6023/cjoc201709040

有机化学 ›› 2018, Vol. 38 ›› Issue (3): 629-635.DOI: 10.6023/cjoc201709040 上一篇下一篇

所属专题：荧光探针-生物传感合辑；有机超分子化学合辑

研究论文

基于香豆素衍生物反应型识别CN^-的紫外荧光传感器及其应用研究

黄青^a,b, 曲文娟^a, 陈洁^c, 林奇^a, 姚虹^a, 张有明^a, 魏太保^a

a 西北师范大学化学化工学院教育部生态环境相关材料重点实验室甘肃省高分子材料重点实验室兰州 730070;
b 宁夏医科大学药学院银川 750006;
c 兰州城市学院兰州 750070

收稿日期:2017-09-25 修回日期:2017-10-31 发布日期:2017-11-17
通讯作者: 魏太保,E-mail:weitaibao@126.com E-mail:weitaibao@126.com
基金资助:
国家自然科学基金（Nos.21662031，21661028，21574104，21262032）资助项目.

A Reaction Type Colorimetric and Fluorescence Chemosensor Based on Coumarin Derivatives Design for Detecting Cyanide Ion and Its Application

Huang Qing^a,b, Qu Wenjuan^a, Chen Jie^c, Lin Qi^a, Yao Hong^a, Zhang Youming^a, Wei Taibao^a

a Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education;Key Laboratory of Polymer Materials of Gansu Province;College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
b School of Pharmacy, Ningxia Medical University, Yinchuan 750006;
c Lanzhou City University, Lanzhou 730070

Received:2017-09-25 Revised:2017-10-31 Published:2017-11-17
Contact: 10.6023/cjoc201709040 E-mail:weitaibao@126.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21662031, 21661028, 21574104, 21262032).

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1. 基于香豆素衍生物反应型识别CN^-的紫外荧光传感器及其应用研究.PDF(406KB)

摘要/Abstract

设计合成了一种基于N-4-吡啶基香豆素-3-甲酰胺的新型的CN^-传感器Q1.通过紫外和荧光光谱研究了传感器Q1对10种不同阴离子的识别性能.当向含水10%（DMSO/H₂O，V：V=9：1）的Q1中分别加入CN^-，F^-，Cl^-，Br^-，I^-，AcO^-，H₂PO₄^-，HSO₄^-，ClO₄^-和SCN^-等阴离子后，发现CN^-的加入，使得Q1在304 nm处的吸收峰增强；相应的荧光光谱在431 nm处产生较强的发射峰；在365 nm紫外灯照射下，加入CN^-的Q1溶液会产生蓝色荧光.同时，其它离子的加入无上述现象.Q1中加入CN^-后光学性质改变的特点可实现在紫外、荧光双通道中检测CN^-，并且对CN^-的检测不受其它竞争离子的干扰.Q1对CN^-的荧光最低检测限为1.44×10^-8 mol/L，低于世界卫生组织（WHO）规定在饮用水中CN^-的最高含量（<1.9μmol/L）.另外，核磁滴定、红外、质谱结果表明，Q1对CN^-可能的识别机理是这二者之间发生加成反应，此推断通过密度泛函计算亦可佐证.值得注意的是，该结果可应用于对樱桃核仁中CN^-的检测，实现了在食物样品中的实时监测.

关键词: 香豆素衍生物, 荧光紫外双通道, 氰根离子, 食物样品应用

A novel CN^- chemosensor based N-4-pyridylcoumarin-3-carboxamide derivative Q1 was designed and synthesized. The recognition performance of sensor Q1 for ten different anions was studied by UV and fluorescence spectroscopy. When anions such as CN^-, F^-, Cl^-, Br^-, I^-, AcO^-, H₂PO₄^-,HSO₄^-,ClO₄^- and SCN^- were added to the mixed solution (DMSO/H₂O, V:V=9:1), addition of CN^- could increase the absorption peak of Q1 at 304 nm, and the corresponding fluorescence produced a strong emission peak at 431 nm. Q1 solution with CN^- emitted strong blue fluorescent that can be easily observed by naked eyes. The color changed (from colorless to faint yellow) and the "Turn-On" fluorescence behavior suggested that Q1 could detect CN^- by dual-channel. Happily, the fluorescent limit of detection (LOD) is 1.44×10^-8 mol/L, was lower than the specified content by World Health Organization (WHO) in drinking water. Based on all the experimental facts, we speculated that the possible identification mechanism was that the addition reaction took place between Q1 and CN^-, and it can also be confirmed by density functional theory (DFT). This result can be applied to the detection of CN^- in cherry kernel.

Key words: coumarin derivatives, dual-channel, cyanide ions, food sample application

引用此文

黄青, 曲文娟, 陈洁, 林奇, 姚虹, 张有明, 魏太保. 基于香豆素衍生物反应型识别CN^-的紫外荧光传感器及其应用研究[J]. 有机化学, 2018, 38(3): 629-635.

Huang Qing, Qu Wenjuan, Chen Jie, Lin Qi, Yao Hong, Zhang Youming, Wei Taibao. A Reaction Type Colorimetric and Fluorescence Chemosensor Based on Coumarin Derivatives Design for Detecting Cyanide Ion and Its Application[J]. Chin. J. Org. Chem., 2018, 38(3): 629-635.

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基于香豆素衍生物反应型识别CN^-的紫外荧光传感器及其应用研究

A Reaction Type Colorimetric and Fluorescence Chemosensor Based on Coumarin Derivatives Design for Detecting Cyanide Ion and Its Application

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