Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1477-1483.DOI: 10.6023/cjoc201801020 Previous Articles     Next Articles

Special Issue: 有机超分子化学合辑



白东a, 周杨b, 卢季红a, 刘青云c, 陈青a, 陶朱a, 肖昕a   

  1. a 贵州大学贵州省大环化学及超分子化学重点实验室 贵阳 550025;
    b 山东师范大学化学化工与材料科学学院 济南 250014;
    c 山东科技大学化学与环境工程学院 青岛 266590
  • 收稿日期:2018-01-13 修回日期:2018-02-08 发布日期:2018-02-11
  • 通讯作者: 肖昕,
  • 基金资助:


Study of the Interaction between Two Kinds of Cucurbit [7]urils and 3-(2-Naphthyl)-alanine

Bai Donga, Zhou Yangb, Lu Jihonga, Liu Qingyunc, Chen Qinga, Tao Zhua, Xiao Xina   

  1. a Key Laboratory of Macrocyclic and Supramolecular Chenmistry of Guizhou Province, Guizhou University, Guiyang 550025;
    b College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014;
    c College of Chemistry and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590
  • Received:2018-01-13 Revised:2018-02-08 Published:2018-02-11
  • Contact: 10.6023/cjoc201801020
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21561007), the Science and Technology Fund of Guizhou Province (No. 2016-1030), the Innovation Program for High-Level Talents of Guizhou Province (No. 2016-5657) and the Major Program for Creative Research Groups of Guizhou Provincial Education Department (No. 2017-028).

The interaction of a pair of amino acid enantiomers, L-3-(2-naphthyl)-alanine (L-NA) and D-3-(2-naphthyl)-alanine (D-NA), with cucurbit[7]uril (Q[7]) and inverted cucurbit[7]uril (iQ[7]) was investigated, respectively, by using NMR spectroscopy, electronic absorption spectroscopy, fluorescence spectroscopies, isothermal titration calorimetry (ITC) experiments and MALDI-TOF mass spectrometry. Furthermore, the similarities and differences of the self-assembly patterns between the two kinds of cucurbituril with different cavity sizes and this pair of amino acid enantiomers were also researched. The results obtained from the experiment revealed that the naphthyl groups of amino acids were all entrapped in the cavity of the Q[n]s, whereas the other section of amino acids remained outside the portal and thus resulted in a more stable supramolecular self-assembly at a 1:1 ratio. Meanwhile, we found that the two different kinds of cucurbit[7]urils showed a slightly different selectivity for the L/D-NA chiral enantiomer.

Key words: inverted cucurbit[7]uril, cucurbit[7]uril, enantiomer, amino acid, self-assembly