七元瓜环与1,7-二(2-苯并咪唑)庚烷的相互作用及自组装

引用本文: 易君明, 陈明华, 薛赛凤, 陶朱. 七元瓜环与1,7-二(2-苯并咪唑)庚烷的相互作用及自组装[J]. 有机化学, 2016, 36(3): 653-658. doi: 10.6023/cjoc201509015 shu

Citation: 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]. Chinese Journal of Organic Chemistry, 2016, 36(3): 653-658. doi: 10.6023/cjoc201509015 shu

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,
,}

1.
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;
2.
b 兴义民族师范学院生物与化学学院兴义 562409

通讯作者: 陶朱

基金项目:
国家自然科学基金(No. 21272045)资助项目. (No. 21272045)

摘要: 利用¹H NMR法、紫外吸收光谱法、荧光发射光谱法和单晶X射线衍射等方法考察了七元瓜环(Q[7])与氯化1,7-二(2-苯并咪唑)庚烷(SBHt)在酸性溶液中的相互作用过程及组装模式. 首先考察了主客体相互作用对客体pK_a的影响, 以确定研究主客体相互作用以及组装过程的实验条件. ¹H NMR滴定实验结果表明, 在水溶液中主客体可形成1:1和2:1的主客体包结配合物, 当主客体物质的量之比为1:1时, Q[7]包结SBHt的烷基链, 两端苯并咪唑基团处于瓜环端口外侧; 当主客体物质的量之比为2:1时, 两个Q[7]分别包结同一SBHt分子的两端苯并咪唑基团, 这一实验结果得到荧光发射光谱的佐证. Q[7]与SBHt形成1:1的主客体包结配合物的晶体结构表明, 客体烷基链在瓜环空腔内发生折叠以使其通过离子偶极及氢键与Q[7]有效作用.

关键词:

English

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

1.
a Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025;
2.
b College of Biology and Chemistry, Xingyi Normal University for Nationalities, Xingyi 562409

Corresponding author: 陶朱

Received Date: 11 September 2015
Available Online: 06 November 2015
Fund Project:
国家自然科学基金(No. 21272045)资助项目.

Abstract: 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

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1.
沈阳化工大学材料科学与工程学院沈阳 110142

七元瓜环与1,7-二(2-苯并咪唑)庚烷的相互作用及自组装

通讯作者: 陶朱

English

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

Corresponding author: 陶朱

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

七元瓜环与1,7-二(2-苯并咪唑)庚烷的相互作用及自组装

通讯作者: 陶朱

English

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

Corresponding author: 陶朱

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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