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Anion‐Templated Calix[4]arene‐Based Pseudorotaxanes and Catenanes
Author(s) -
Lankshear Michael D.,
Evans Nicholas H.,
Bayly Simon R.,
Beer Paul D.
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200700041
Subject(s) - catenane , chemistry , pyridinium , hexafluorophosphate , ion , calixarene , hydrogen bond , metathesis , supramolecular chemistry , stereochemistry , molecule , crystallography , combinatorial chemistry , polymer chemistry , medicinal chemistry , organic chemistry , ionic liquid , polymerization , polymer , catalysis
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 14 a for hexafluorophosphate gives catenane 14 d , 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.