有机化学 ›› 2018, Vol. 38 ›› Issue (11): 3094-3100.DOI: 10.6023/cjoc201807047 上一篇    下一篇

所属专题: 有机超分子化学合辑 有机小分子-金属协同催化

研究简报

三种瓜环与苯并吲唑衍生物的超分子自组装

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 E-mail:gyhxxiaoxin@163.com
  • 基金资助:

    国家自然科学基金(Nos.21561007,21861011)、贵州省科学基金(No.2016-1030)、贵州省高层次创新型人才培养计划(No.2016-5657)和贵州省教育厅创新群体重大研究(No.2017-028)资助项目.

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).

设计、合成了医药中间体3-吡啶基苯并吲唑衍生物(DIHY)作为客体分子,并利用1H NMR、质谱、等温量热滴定和紫外吸收光谱法考察了主体对称四甲基六元瓜环(TMeQ[6])、七元瓜环(Q[7])以及八元瓜环(Q[8])和与其相互作用的结构特征.结果表明,这三种具有不同空腔大小的瓜环与DIHY之间具有不同的作用模式.TMeQ[6]-DIHY体系中,客体分子位于瓜环的端口处;Q[7]-DIHY体系中,客体分子DIHY的4,5-二氢-2H-苯并吲唑部分进入到瓜环的空腔内部,而吡啶基团位于瓜环的端口形成1:1的类轮烷结构;Q[8]-DIHY体系中,2个客体分子DIHY的4,5-二氢-2H-苯并吲唑部分以"面对面"的堆叠方式进入到Q[8]的空腔中,而吡啶基团位于瓜环的端口,自组装形成1:2的超分子结构.

关键词: 瓜环, 类轮烷, 超分子

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