基于芳基炔醛共轭延伸的1,8-萘酰亚胺的高选择性比色和荧光氰离子探针
收稿日期: 2016-05-16
修回日期: 2016-06-13
网络出版日期: 2016-07-08
基金资助
国家自然科学基金（No.21202099）、上海市科委地方院校能力建设（No.15120503700）资助项目.
A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide
Received date: 2016-05-16
Revised date: 2016-06-13
Online published: 2016-07-08
Supported by
Project supported by the National Natural Science Foundation of China (No.21202099),and the Science and Technology Commission of Shanghai Municipality (No.15120503700).
以N-丁基-4-溴-6-硝基-1，8-萘酰亚胺与邻炔基苯甲醛经Sonogashira偶联反应合成了1个高选择性的氰根离子荧光探针4.在乙腈溶液中，探针4对氰根离子具有比色和荧光双重响应.加入氰根离子后，探针4的紫外-可见光谱在540 nm处产生新吸收峰，溶液由无色变成浅紫色，其他阴离子对探针4的紫外-可见光谱几乎无影响.无CN-存在时，探针4的荧光光谱在484 nm附近产生强荧光，加入CN-后，484 nm处的发射带逐渐消失，同时在600 nm附近产生一组新峰，荧光颜色从浅绿色变成浅棕色.这归因于CN-对不饱和醛基进行加成，进而通过共轭炔基影响萘酰亚胺荧光团上的电荷转移.同时，探针4在乙腈/水（体积比9：1）混合体系对阴离子的干扰实验进行了详细的研究.
赵飞飞 , 伍宏伟 , 刘传祥 , 毛海舫 . 基于芳基炔醛共轭延伸的1,8-萘酰亚胺的高选择性比色和荧光氰离子探针[J]. 有机化学, 2016 , 36(11) : 2689 -2694 . DOI: 10.6023/cjoc201605027
A high selective fluorescent probe 4 for cyanides was developed based on the Sonogashira reaction between N-butyl-4-bromo-1,8-naphthalimide and 2-ethynylbenzaldehyde. In CH3CN solution, the probe 4 shows moderate colorimetric and fluorescent response to the cyanides. Upon the addition of TBACN, a new peak at 540 nm appeared in the UV-vis spectra accompanied by an instant colorimetric change from colorless to light violet. No change in the spectral pattern of chemosensor 4 was observed in the presence of other anions. Further, chemosensor 4 showed strong fluorescence with the maximum at 484 nm (λex=390 nm) in a mixture of CH3CN; however, in presence of CN-, a new emission band (λem=600 nm, light brown fluo-rescence) appeared along with a decrease in the emission intensity at 484 nm. Therefore, this process clearly demonstrates that chemosensor 4 can selectively detect cyanide ions by a fluorogenic "on-off" response, which may be attributed to the fact that the electron transfer in 1,8-naphthalimide is affected by the formation of adducts of anion with carbonyl groups. Moreover, the detailed interference experiments of chemosensor 4 in the mixed solvents were also investigated.
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