Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Anion-templated calix[4]arene-based pseudorotaxanes and catenanes
AU - Lankshear, Michael D.
AU - Evans, Nicholas H.
AU - Bayly, Sinion R.
AU - Beer, Paul D.
PY - 2007/5/7
Y1 - 2007/5/7
N2 - 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.
AB - 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.
KW - anions
KW - calixarenes
KW - catenanes
KW - self-assembly
KW - supramolecular chemistry
KW - ROTAXANE SYNTHESIS
KW - OLEFIN METATHESIS
KW - INTERLOCKED MOLECULES
KW - ORGANIC-SYNTHESIS
KW - CROWN-ETHERS
KW - RECOGNITION
KW - COORDINATION
KW - RECEPTORS
KW - CHEMISTRY
KW - RINGS
U2 - 10.1002/chem.200700041
DO - 10.1002/chem.200700041
M3 - Journal article
VL - 13
SP - 3861
EP - 3870
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 14
ER -