Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 561-565.DOI: 10.6023/cjoc201310023 Previous Articles     Next Articles


刘瑞源a, 勇雪b, 杨小东b, 严轶琛a, 路新卫a, 瞿金清b   

  1. a 南方医科大学药学院 广州 510515;
    b 华南理工大学化学与化工学院 广州 510640
  • 收稿日期:2013-10-17 修回日期:2013-11-20 发布日期:2013-11-28
  • 通讯作者: 刘瑞源,瞿金清;
  • 基金资助:

    国家自然科学基金(No. 21244007)资助项目.

Fluoride Ion Probe Based on 2-Thiohydantoin

Liu Ruiyuana, Yong Xueb, Yang Xiaodongb, Yan Yichena, Lu Xinweia, Qu Jinqingb   

  1. a School of Pharmaceutical Science, Southern Medical University, Guangzhou 510515, China;
    b School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, China
  • Received:2013-10-17 Revised:2013-11-20 Published:2013-11-28
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21244007).

2-Thiohydantoin derivatives 1 and 2 were synthesized by the reaction of isoleucine methyl ester hydrochloride with 4-nitro-phenyl isothiocyanate or 4-cyano-phenyl isothiocyanate. The anion sensing ability of 1 and 2 was estimated via tetra-n-butylammonium (TBA) salts of a series of anions in N,N-dimethyl formamide (DMF). After the addition of F-, the color of the DMF solution of 1 and 2 immediately changes from colorless to yellow, while the color of solution changes slightly by the addition of Cl-, Br-, and. The experimental facts indicate that 1 and 2 exhibit high selectivity sensing ability to F-. The 1H NMR titrations of 1 and 2 reveal that the colorimetric response of 1 and 2 are triggered by the hydrogen bonding interaction between 2-thiohydantoin and F-. Binding constants confirmed that 1 is more sensible to F- than 2. Furthermore, 1 can also be used as a chemosensor for the detection of F- in test paper.

Key words: 2-thiohydantoin, colorimetric sensor, anion recognition, fluoride ion