Synthesis and Characterization of Pseudorotaxanes with Terminal Alkenyl Group——Supramolecular Self-assemblies of  Cucurbit[6]uril and Alkenyl-terminated Viologen

Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (11): 1937-1942. Previous Articles Next Articles

Original Articles

端基含活性烯基的准轮烷的合成及表征——葫芦[6]脲与端烯基紫精的超分子自组装

侯昭升^*,a ; 许静^b; 陈云深^a ; 谭业邦^c; 阚成友^a

(a清华大学化工系高分子研究所教育部先进材料重点实验室北京 100084)
(b山东轻工业学院分析测试中心济南250353)
(c山东大学化学与化工学院济南 250100)

收稿日期:2007-11-22 修回日期:2008-02-27 发布日期:2008-11-18
通讯作者: 侯昭升

Synthesis and Characterization of Pseudorotaxanes with Terminal Alkenyl Group——Supramolecular Self-assemblies of Cucurbit[6]uril and Alkenyl-terminated Viologen

HOU, Zhao-Sheng^*,a ; XU, Jing ^b; CHEN, Yun-Shen ^a; TAN, Ye-Bang ^c; KAN, Cheng-You^a

(a Key Laboratory of Advanced Materials of Ministry of Education, Institute of Polymer Science and Engineering,
Department of Chemical Engineering, Tsinghua University, Beijing 100084)
(b Instrumental Analysis Center, Shandong Institute of Light Industry, Jinan 250353)
(c School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100)

Received:2007-11-22 Revised:2008-02-27 Published:2008-11-18
Contact: HOU, Zhao-Sheng

Abstract

A water soluble pseudorotaxane (4VBVBuCB) with an active terminal alkenyl group was synthesized by supramolecular self-assembly of cucurbit[6]uril (CB[6]) with alkenyl-terminated viologen [N-n-butyl-N’-(p-vinylbenzyl)-4,4’-bipyridinium bromide chloride, 4VBVBu] in water at room temperature. The chemical structures of 4VBVBu and 4VBVBuCB were confirmed by elemental analysis, 1H NMR and IR spectra. CB[6] beads are localized on terminal aliphatic chain to combine N＋of 4VBVBu by non-covalent bonds, and the molar ratio of CB[6] to 4VBVBu is 1∶1. The results of thermogravimetry analysis (TGA), UV-Vis measurements show that 4VBVBuCB has higher thermal stability and stronger absorption band than 4VBVBu. The effect of salts on 4VBVBuCB was studied by the transmittance with UV-Vis, and the result shows that NaI is the satisfying precipitant to 4VBVBuCB. The microscopical morphologies of 4VBVBu and 4VBVBuCB were studied by environmental scanning electron microscopy (ESEM), and the results show that 4VBVBuCB has higher rigidity and lower crystallizability than 4VBVBu.

Key words: terminal alkenyl, pseudorotaxane, viologen, supramolecular self-assembly, cucurbit[6]uril

Cite this article

HOU, Zhao-Sheng^*,a ; XU, Jing ^b; CHEN, Yun-Shen ^a; TAN, Ye-Bang ^c; KAN, Cheng-You^a
. Synthesis and Characterization of Pseudorotaxanes with Terminal Alkenyl Group——Supramolecular Self-assemblies of Cucurbit[6]uril and Alkenyl-terminated Viologen[J]. Chin. J. Org. Chem., 2008, 28(11): 1937-1942.

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端基含活性烯基的准轮烷的合成及表征——葫芦[6]脲与端烯基紫精的超分子自组装

Synthesis and Characterization of Pseudorotaxanes with Terminal Alkenyl Group——Supramolecular Self-assemblies of Cucurbit[6]uril and Alkenyl-terminated Viologen

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