Bis(benzimidazolium) axles and crown ether wheels: a versatile templating pair for the formation of [2]rotaxane molecular shuttles

被引:70
作者
Zhu, Kelong [1 ]
Vukotic, V. Nicholas [1 ]
Noujeim, Nadim [1 ]
Loeb, Stephen J. [1 ]
机构
[1] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
DRIVEN; ROTAXANES; FRAMEWORKS; CATENANES;
D O I
10.1039/c2sc20986a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Condensation of an aldehyde appended benzimidazolium cation with a 1,2-benzenediamine in the presence of a crown ether allows formation of a second benzimidazole group and the facile synthesis of a [2]rotaxane molecular shuttle. The ease of this reaction and the versatility of the initial templating interaction between the benzimidazolium cation and crown ether allows for the preparation of [2] rotaxane molecular shuttles with crown ether macrocycles of various shapes and sizes. The synthesis and dynamic properties of a set of five [2]rotaxane molecular shuttles are described including the first examples of rotaxanes containing the larger macrocycles dibenzo[30]crown-10 (DB30C10) and bis-meta-phenylene-[26]crown-8 (BMP26C8).
引用
收藏
页码:3265 / 3271
页数:7
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