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 -