Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 52, Pages 17751-17765Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303122
Keywords
anions; molecular dynamics; preorganisation; rotaxanes; triazolium
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Funding
- Clarendon Fund
- Trinity College Oxford
- University of Oxford's Vice-Chancellors' Fund
- FCT [SFRH/BPD/42357/2007]
- project New Strategies Applied to Neuropathological Disorders [CENTRO-07-ST24-FEDER-002034]
- QREN, Mais Centro- Programa Operacional Regional do Centro e Uniao Europeia/Fundo Europeu de Desenvolvimento Regional
- Fundação para a Ciência e a Tecnologia [SFRH/BPD/42357/2007] Funding Source: FCT
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Three triazolium-based [2]rotaxanes containing different sized axle and macrocycle components were synthesised in good yields (40-57%) through chloride anion templation. The anion recognition properties of the interlocked receptor systems were investigated using (HNMR)-H-1 titration experiments: all three rotaxanes display impressive selectivities for halide anions over the more basic oxoanion acetate. The rotaxanes incorporating shorter, more rigid axle components with aryl-substituted triazolium groups display substantially higher anion binding affinities than those with longer, bis-alkyl-substituted heterocycles, which is attributed to the increased intercomponent preorganisation afforded by the smaller axle component. Computational DFT and molecular dynamics simulations composed of unconstrained and umbrella sampling simulations corroborate the experimental observations.
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