Issue 11, 2012

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

Abstract

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).

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

Supplementary files

Article information

Article type
Edge Article
Submitted
17 Jul 2012
Accepted
08 Aug 2012
First published
09 Aug 2012

Chem. Sci., 2012,3, 3265-3271

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

K. Zhu, V. N. Vukotic, N. Noujeim and S. J. Loeb, Chem. Sci., 2012, 3, 3265 DOI: 10.1039/C2SC20986A

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