Citation: Zhao Feifei, Wu Hongwei, Liu Chuanxiang, Mao Haifang. A Selective Colorimetric and Fluorescent Diphenylacetylene-Based Naphthalimide for Sensing of Cyanide[J]. Chinese Journal of Organic Chemistry, ;2016, 36(11): 2689-2694. doi: 10.6023/cjoc201605027 shu

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

1.
School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418

Corresponding author: Liu Chuanxiang, cxliu@sit.edu.cn Mao Haifang, mhf@sit.edu.cn
Received Date: 16 May 2016
Revised Date: 13 June 2016

Fund Project: the Science and Technology Commission of Shanghai Municipality 15120503700the National Natural Science Foundation of China 21202099

Figures(8)

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.
- 1, 8-naphlimide,
- anion recognition,
- cyanides,
- nucleophilic addition,
- fluorescent probe
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