Fluoride Ion Probe Based on 2-Thiohydantoin

doi:10.6023/cjoc201310023

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

基于2-硫代海因的氟离子探针

刘瑞源^a, 勇雪^b, 杨小东^b, 严轶琛^a, 路新卫^a, 瞿金清^b

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 E-mail:ruiyliu@smu.edu.cn；cejqqu@scut.edu.cn
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 Ruiyuan^a, Yong Xue^b, Yang Xiaodong^b, Yan Yichen^a, Lu Xinwei^a, Qu Jinqing^b

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

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Liu Ruiyuan, Yong Xue, Yang Xiaodong, Yan Yichen, Lu Xinwei, Qu Jinqing. Fluoride Ion Probe Based on 2-Thiohydantoin[J]. Chin. J. Org. Chem., 2014, 34(3): 561-565.

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基于2-硫代海因的氟离子探针

Fluoride Ion Probe Based on 2-Thiohydantoin

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