用于检测三苯基膦的一种新型“点亮”型荧光探针

doi:10.7517/j.issn.1674-0475.2017.05.013

影像科学与光化学 ›› 2017, Vol. 35 ›› Issue (6): 771-779.DOI: 10.7517/j.issn.1674-0475.2017.05.013

用于检测三苯基膦的一种新型“点亮”型荧光探针

黄振涛, 王楠楠, 张健, 赵伟利

河南大学特种功能材料教育部重点实验室, 河南开封 475004

收稿日期:2017-05-29 修回日期:2017-06-13 出版日期:2017-11-15 发布日期:2017-11-15
通讯作者: 张健, 赵伟利
基金资助:
国家自然科学基金（21372063）资助

A Novel Turn-on Fluorescent Probe for Triphenylphosphine

HUANG Zhentao, WANG Nannan, ZHANG Jian, ZHAO Weili

Key Laboratory for Special Functional Materials of the Ministry of Education, Henan University, Kaifeng 475004, Henan, P. R. China

Received:2017-05-29 Revised:2017-06-13 Online:2017-11-15 Published:2017-11-15
Supported by:
Porject supported by the National Natural Science Foundations of China (11371240);the Shanghai Municipal Education Commission of Scientific Research Innovation Project (11ZZ84)

摘要/Abstract

摘要：

三苯基膦（简称PPh₃）是一种重要的有机物质并有独特的亲核性和还原性，广泛应用于有机及有机金属物质的合成。PPh₃的广泛使用不可避免地导致对环境的污染，给人类的健康带来危害，因此，亟需一种简单高效的检测手段实现对三苯基膦的检测识别。在本工作中，我们效仿Staudinger连接反应设计合成了一个具有高选择性和高灵敏度的荧光增强型探针用以检测三苯基膦。探针的设计思想是使用荧光素的邻叠氮苯乙酯衍生物与PPh₃反应，通过生成的氮杂叶立德，经由分子内酰基转移释放荧光团。该探针在含0.5%的DMSO水溶液中显示对PPh₃的高选择性响应，可望在线性范围1×10^-7 mol/L至8×10^-7 mol/L之间实现对PPh₃的定量检测，其检测极限达到10 nmol/L。对PPh₃的灵敏检测可达到在水溶液中肉眼可视。

关键词: 荧光素, 荧光探针, 荧光增强型响应, 三苯基膦, Staudinger连接

Abstract:

Triphenylphosphine (PPh₃) is an important organic substance and extraordinary for its nucleophilicity and reducing character.It is widely used in the synthesis of organic and organometallic compounds.The extensive use of PPh₃ is inevitable to cause phosphorous pollution to the environment and would pose a potential danger to human health.An effective and convenient detection method of PPh₃ is fairly desirable.Herein,a novel selective and sensitive off-on fluorescent probe for PPh₃ mimicking Staudinger ligation was developed.The design concept was to use a 2-azidophenylacetic ester of fluorescein to react with PPh₃ to undergo a rapid intramolecular acyl transfer through aza-ylide intermediate to release the fluorophore.The probe shows highly selective response to PPh₃ in water containing 0.5% DMSO.The probe is promising for the quantitative detection of PPh₃ with linear response from 1×10^-7 mol/L to 8×10^-7 mol/L with a detection limit of 10 nmol/L.The sensitive detection of PPh₃ can be viewed in water solutions with "naked eye".

Key words: fluorescein, fluorescent probe, turn-on fluorescent response, triphenylphosphine, Staudinger ligation

黄振涛, 王楠楠, 张健, 赵伟利. 用于检测三苯基膦的一种新型“点亮”型荧光探针[J]. 影像科学与光化学, 2017, 35(6): 771-779.

HUANG Zhentao, WANG Nannan, ZHANG Jian, ZHAO Weili. A Novel Turn-on Fluorescent Probe for Triphenylphosphine[J]. Imaging Science and Photochemistry, 2017, 35(6): 771-779.

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用于检测三苯基膦的一种新型“点亮”型荧光探针

A Novel Turn-on Fluorescent Probe for Triphenylphosphine

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