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



赵飞飞, 伍宏伟, 刘传祥, 毛海舫   

  1. 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;
  • 基金资助:


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

Zhao Feifei, Wu Hongwei, Liu Chuanxiang, Mao Haifang   

  1. 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).

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.

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