Chinese Journal of Organic Chemistry >
Fluoride Ion Probe Based on 2-Thiohydantoin
Received date: 2013-10-17
Revised date: 2013-11-20
Online 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
Liu Ruiyuan , Yong Xue , Yang Xiaodong , Yan Yichen , Lu Xinwei , Qu Jinqing . Fluoride Ion Probe Based on 2-Thiohydantoin[J]. Chinese Journal of Organic Chemistry, 2014 , 34(3) : 561 -565 . DOI: 10.6023/cjoc201310023
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