Interaction and Supramocular Self-Assembly of Cucurbit[7]uril with 2,2'-(Heptane-1,7-diyl) Dibenzimidazolium Chloride

doi:10.6023/cjoc201509015

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 653-658.DOI: 10.6023/cjoc201509015 Previous Articles Next Articles

Notes

七元瓜环与1,7-二(2-苯并咪唑)庚烷的相互作用及自组装

易君明^a,b, 陈明华^b, 薛赛凤^a, 陶朱^a

a 贵州大学贵州省大环化学与超分子化学重点实验室贵阳 550025;
b 兴义民族师范学院生物与化学学院兴义 562409

收稿日期:2015-09-11 修回日期:2015-10-31 发布日期:2015-11-06
通讯作者: 陶朱 E-mail:gzutao@263.net
基金资助:
国家自然科学基金(No. 21272045)资助项目.

Interaction and Supramocular Self-Assembly of Cucurbit[7]uril with 2,2'-(Heptane-1,7-diyl) Dibenzimidazolium Chloride

Yi Junming^a,b, Chen Minghua^b, Xue Saifeng^a, Tao Zhu^a

a Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025;
b College of Biology and Chemistry, Xingyi Normal University for Nationalities, Xingyi 562409

Received:2015-09-11 Revised:2015-10-31 Published:2015-11-06
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272045).

The interaction and supramolecular self-assembly of cucurbit[7]uril (Q[7]) with 2,2'-(heptane-1,7-diyl) dibenzimidazolium chloride (SBHt) in aqueous solution were investigated by ¹H NMR spectroscopy, fluorescence spectroscopy in details. The pK_a shift of guest in the presence of Q[7] was first investigated in order to decide the pH of medium condition for investigation of host-guest interaction and supramolecular self-assembly. ¹H NMR spectroscopy analysis revealed that Q[7] included the alkylene chain of guest and formed a simple 1:1 host-guest binding model complex at a low rate of N_Q[7]/N_SBHt, while at higher ratios of Q[7] to guest, two host Q[7] prefer to include the benzimidazolyl moieties of guest and formed a dumbbell shape inclusion complex. The typical reversible interaction modes were controlled by concentration of the ratio of host and guest, and the process was further conformed by fluorescence spectroscopy technology. The single X-ray crystal structure analysis showed a 1:1 host-guest inclusion complex in which the alkyl chain of SBHt was folded in order to effectively interact with Q[7] through ion-dipole interactions and hydrogen bonding.

Key words: cucurbit[7]uril, 2,2'-(heptane-1,7-dily)dibenzimidazolium, interaction, supramolecular self-assembling, crystal structure

Cite this article

Yi Junming, Chen Minghua, Xue Saifeng, Tao Zhu. Interaction and Supramocular Self-Assembly of Cucurbit[7]uril with 2,2'-(Heptane-1,7-diyl) Dibenzimidazolium Chloride[J]. Chin. J. Org. Chem., 2016, 36(3): 653-658.

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七元瓜环与1,7-二(2-苯并咪唑)庚烷的相互作用及自组装

Interaction and Supramocular Self-Assembly of Cucurbit[7]uril with 2,2'-(Heptane-1,7-diyl) Dibenzimidazolium Chloride

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