Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 3094-3100.DOI: 10.6023/cjoc201807047 Previous Articles     Next Articles

Special Issue: 有机小分子-金属协同催化 有机超分子化学合辑



王海燕a, 阚京兰b, 边炳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:2018-07-26 修回日期:2018-09-11 发布日期:2018-10-12
  • 通讯作者: 肖昕
  • 基金资助:


Self-Assembly Modes of Three Cucurbit[n] urils with Benzoindazole Derivative

Wang Haiyana, Kan Jinglanb, Bian Bingc, 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, Qingda 266590
  • Received:2018-07-26 Revised:2018-09-11 Published:2018-10-12
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21561007, 21861011), 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).

A pharmaceutical intermediate, 3-pyridyl benzoxazole derivatives (DIHY), was designed and synthesized as the guest molecule. The self-assembly binding models of tetramethyl cucurbit[6] uril (TMeQ[6]), cucurbit[7] uril (Q[7]) and cucurbit[8] uril (Q[8]) with DIHY were investigated by 1H NMR, MS, isothermal titration calorimetry and UV-Vis spectrum. The results showed that there are different modes of interaction between these three different cucurbit[n] uril and DIHY. For the TMeQ[6]-DIHY system, the guest molecule is located at the port of the TMeQ[6], while for the Q[7]-DIHY system, the 4,5-dihydro-2H-benzoxazole moiety of the guest molecule reside within the cavity of Q[7] host, whereas the pyridyl group of DIHY guest remains outside of the portal to form the 1:1 inclusion complexes of pseudorotaxane structure. Nevertheless, the 4,5-dihydro-2H-benzoxazole moiety of two guest molecule is included in the cavity of Q[8] host in a "face to face" stacking way, while the pyridine group of DIHY is located at the port of Q[8] to form a 1:2 supramolecular structure.

Key words: cucurbit[n]uril, pseudorotaxane, supramolecular