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Citation: WU Jawei, TANG Rongping, SUO Longning, YANG Xingkai, WEI Taibao, ZHOU Yanqing. Synthesis of Molecular Tweezers Based on Thiosemi-Carbazide and Their Anion Recognition Properties[J]. Chinese Journal of Applied Chemistry, ;2011, 28(11): 1274-1279. doi: 10.3724/SP.J.1095.2011.00688 shu

Synthesis of Molecular Tweezers Based on Thiosemi-Carbazide and Their Anion Recognition Properties

1.
a Department of Petrochemial Engineering, Lanzhou Petrochemical College of Vocational Technology, Lanzhou 730060;
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b College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: ZHOU Yanqing,
Received Date: 18 November 2010
Available Online: 13 March 2011
Fund Project: 国家自然科学基金(20671077) (20671077)甘肃省省属高校基本科研业务费资助项目甘财教(2009-192) (2009-192)

Two novel molecular receptors based on thiosemicarbazide, compound 3a(1, 3-bis(otolueneoxoacetylthio-semicarbazideacyl) benzene) and compound 3b(1, 3-bis(p-tolueneoxoacetylthiosemicarbazideacyl) benzene), have been designed and synthesized under solid-liquid phase transfer catalysis conditions. The binding properties for anions such as F^-, AcO^-, Cl^-, Br^- and I^- in DMSO have been examined by UV-Vis and ¹H NMR spectroscopy. The results show a high selectivity for F^- and AcO^-, however, no obvious interaction was found for Cl^-, Br^-, and I-. The ¹H NMR combined with Job curves indicates that a 1:1 stoichiometry complex is formed between the receptors and the anions through hydrogen bonding interactions. In view of these results, the influences of the number of NH binding points and steric effect on binding properties were discussed. The receptor compound 3b can form much more hydrogen-bonding interactions due to the presence of many NH binding points, with larger association constant(K_s) than that of thiourea receptor. Compared compound 3a with 3b, large steric effect prevent the combination between compound 3a and anions. In terms of F^- and AcO^-, association constant of compound 3a and 3b followed the same tendency K_s(F^-) >K_s(AcO^-), owing to the better fit of size and shape between the receptors and F^-.
- molecular tweezers,
- thiosemicarbazide,
- anion recognition
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