有机化学 ›› 2020, Vol. 40 ›› Issue (1): 175-180.DOI: 10.6023/cjoc201907042 上一篇    下一篇

研究论文

基于柱[5]芳烃主客体包结构筑分子响应型超分子水凝胶

王姣, 姚虹, 周琦, 阚晓彤, 樊彦青, 关晓文, 张有明, 林奇, 魏太保   

  1. 西北师范大学化学化工学院 甘肃省生态环境高分子材料重点实验室 生态功能高分子材料教育部重点实验室 兰州 730070
  • 收稿日期:2019-07-27 修回日期:2019-09-07 出版日期:2020-01-25 发布日期:2019-09-18
  • 通讯作者: 姚虹, 魏太保 E-mail:yhxbz@126.com;weitaibao@126.com
  • 基金资助:
    国家自然科学基金(Nos.21662031,21661028,21574104)资助项目.

Molecule-Responsive Supramolecular Hydrogel Constructed from Pillar[5]arene Based on Host-Guest System

Wang Jiao, Yao Hong, Zhou Qi, Kan Xiaotong, Fan Yanqing, Guan Xiaowen, Zhang Youming, Lin Qi, Wei Taibao   

  1. Key Laboratory of Eco-environmental Polymer Materials of Gansu Province, Key Laboratory of Eco-functional Polymer Materials of the Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070
  • Received:2019-07-27 Revised:2019-09-07 Online:2020-01-25 Published:2019-09-18
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21662031, 21661028, 21574104).

主客体相互作用是在水溶液中与大环主体分子形成稳定的包结物的理想驱动力.以功能化的苯并咪唑衍生物为客体(M),水溶性柱[5]芳烃为主体构建了一种分子响应型超分子水凝胶.通过1H NMR,2D NOESY和扫描电子显微镜(SEM)研究了水凝胶的成凝胶机理.有趣的是,主客体包结作用、柱[5]芳烃间有序的"外腔"π-π相互作用和分层堆积对于获得超分子水凝胶是必不可少的,非共价键相互作用的动态可逆性使凝胶体系对温度变化/化学刺激产生响应.此外,加入竞争性客体己二腈(ADN)/百草枯(PQ)后,柱[5]芳烃基水凝胶可转化为溶胶.因此,该超分子水凝胶可以选择性识别有机分子.

关键词: 超分子水凝胶, 水溶性柱[5]芳烃, 竞争包结, 分子识别, 自组装

The host-guest interaction was qualified as an ideal drive force to form stable inclusion complexes with macrocyclic host molecules in aqueous solution. Herein, a multi-responsive supramolecular hydrogel was constructed based on a functionalized benzimidazole derivative guest (M) with soluble pillar[5]arene as a host group. The mechanism of hydrogel formation was explored by the 1H NMR, 2D NOESY and scanning electron microscope (SEM) in depth study. Interestingly, host-guest inclusion, the ordered "exo-wall" π-π interaction and hierarchical stacking of pillar[5]arene was indispensable to obtain the supramolecular hydrogel, which endowed the gel system with response to temperature change/chemical stimuli. Upon addition of competitive guests adiponitrile (ADN)/paraquat (PQ), pillar[5]arene-based hydrogel could be converted into sol. Herein, the organic molecules could be selectively recognized by the hydrogel.

Key words: supramolecular hydrogel, soluble pillar[5]arene, competitive inclusion, molecular recognition, self assembly