Anion-templated calix[4]arene-based pseudorotaxanes and catenanes

Lankshear, Michael D. and Evans, Nicholas H. and Bayly, Sinion R. and Beer, Paul D. (2007) Anion-templated calix[4]arene-based pseudorotaxanes and catenanes. Chemistry - A European Journal, 13 (14). pp. 3861-3870. ISSN 0947-6539

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Abstract

We present the rational design and anion-binding properties of the first anion-templated pseudorotaxanes and catenanes in which the "wheel" component is provided by a calix[4]arene macrobicyclic unit. The designs and syntheses of two new calix[4]arene macrobicycles, 2 and 3, are presented, and the abilities of these new species both to bind anions and to undergo anion-dependent pseudorotaxane formation are demonstrated. Furthermore, it is shown that performing ring-closing metathesis reactions on some of these pseudorotaxane assemblies gives novel catenane species 14 and 15, in which the yield of interlocked molecule obtained is critically dependent on the presence of a suitable anion template, namely, chloride. Exchange of the chloride anion in catenane 14a for hexafluorophosphate gives catenane 14d, which contains a unique anion-binding domain defined by the permanently interlocked hydrogen-bond-donating calix[4]arene macrobicycle and pyridinium macrocycle fragments. The anion-binding properties of this domain are presented, and shown to differ from non-interlocked components.

Item Type:
Journal Article
Journal or Publication Title:
Chemistry - A European Journal
Uncontrolled Keywords:
/dk/atira/pure/subjectarea/asjc/1600
Subjects:
ID Code:
65931
Deposited By:
Deposited On:
07 Aug 2013 10:30
Refereed?:
Yes
Published?:
Published
Last Modified:
11 Mar 2020 03:57