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A [3]Rotaxane of the Amide Type

Fritz Vögtle, Thomas Dünnwald, Mirko Händel, Ralf Jäger, Stephan Meier, G. Harder

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Abstract

Abstract Two new rotaxane types, the [2]rotaxanes 12a,b and the [3]rotaxane 13 , have been synthesised by treating the “axle” 7 with the stopper component 9 in the presence of the “wheel” 8 . A nonionic template intermediate of type 10 is proposed. The [3]rotaxane 13 was only obtained when the chain of the “axle” had a certain length: with n = 1 only [2]rotaxane 12 a was isolated, whereas with n = 2 the [3]rotaxane 13 was formed besides the [2]rotaxane 12 b . This suggests that more extended rotaxanes and polyrotaxanes can be synthesised by the template strategy.

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What this paper is about

Abstract Two new rotaxane types, the [2]rotaxanes 12a,b and the [3]rotaxane 13 , have been synthesised by treating the “axle” 7 with the stopper component 9 in the presence of the “wheel” 8 . A nonionic template intermediate of type 10 is proposed. The [3]rotaxane 13 was only obtained when the chain of the “axle” had a certain length: with n = 1 only [2]rotaxane 12 a was isolated, whereas with n = 2 the [3]rotaxane 13 was formed besides the [2]rotaxane 12 b . This suggests that more extended rotaxanes and polyrotaxanes can be synthesised by the template strategy.

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Available abstract

Abstract Two new rotaxane types, the [2]rotaxanes 12a,b and the [3]rotaxane 13 , have been synthesised by treating the “axle” 7 with the stopper component 9 in the presence of the “wheel” 8 . A nonionic template intermediate of type 10 is proposed. The [3]rotaxane 13 was only obtained when the chain of the “axle” had a certain length: with n = 1 only [2]rotaxane 12 a was isolated, whereas with n = 2 the [3]rotaxane 13 was formed besides the [2]rotaxane 12 b . This suggests that more extended rotaxanes and polyrotaxanes can be synthesised by the template strategy.

Key concepts: Rotaxane, Axle, Amide, Stereochemistry, Chemistry, Materials science, Crystallography, Organic chemistry

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