A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide

doi:10.6023/cjoc201605027

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (11): 2689-2694.DOI: 10.6023/cjoc201605027 Previous Articles Next Articles

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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

赵飞飞, 伍宏伟, 刘传祥, 毛海舫

上海应用技术大学化学与环境工程学院上海 201418

收稿日期:2016-05-16 修回日期:2016-06-13 发布日期:2016-07-08
通讯作者: 刘传祥, 毛海舫 E-mail:cxliu@sit.edu.cn;mhf@sit.edu.cn
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

Zhao Feifei, Wu Hongwei, Liu Chuanxiang, Mao Haifang

School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418

Received:2016-05-16 Revised:2016-06-13 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).

1. A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide.PDF(833KB)

Abstract

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 (λ_ex=390 nm) in a mixture of CH₃CN; however, in presence of CN^-, a new emission band (λ_em=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.

Key words: 1,8-naphlimide, anion recognition, cyanides, nucleophilic addition, fluorescent probe

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Zhao Feifei, Wu Hongwei, Liu Chuanxiang, Mao Haifang. A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide[J]. Chin. J. Org. Chem., 2016, 36(11): 2689-2694.

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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

A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide

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