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

Kelong Zhu; V. Nicholas Vukotic; Nadim Noujeim; Stephen J. Loeb

doi:10.1039/C2SC20986A

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

Kelong Zhu,^a V. Nicholas Vukotic,^a Nadim Noujeim^a and Stephen J. Loeb*^a

* Corresponding authors

^a Department of Chemistry and Biochemistry, University of Windsor, Windsor, Canada
E-mail: loeb@uwindsor.ca
Fax: +1-519-973-7098
Tel: +1-519-253-3000

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).

Supplementary files

Publication details

The article was received on 17 Jul 2012, accepted on 08 Aug 2012 and first published on 09 Aug 2012

Article type: Edge Article

DOI: 10.1039/C2SC20986A

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

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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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Chemical Science

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

Abstract

Supplementary files

Publication details

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

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