A Chiral Halogen-Bonding [3]Rotaxane for the Recognition and Sensing of Biologically Relevant Dicarboxylate Anions
authors Lim, JYC; Marques, I; Felix, V; Beer, PD
nationality International
journal ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
author keywords dicarboxylates; halogen bonding; molecular dynamics; molecular recognition; rotaxanes
keywords ELECTROCHEMICAL CO2 REDUCTION; CARBON-DIOXIDE REDUCTION; OXIDATION-KINETICS; COPPER-CATALYSTS; ELECTROREDUCTION; SURFACES; ETHYLENE; NANOPARTICLES; HYDROCARBONS; SELECTIVITY
abstract The unprecedented application of a chiral halogen-bonding [3] rotaxane host system for the discrimination of stereo- and E/Z geometric isomers of a dicarboxylate anion guest is described. Synthesised by a chloride anion templation strategy, the [3] rotaxane host recognises dicarboxylates through the formation of 1: 1 stoichiometric sandwich complexes. This process was analysed by molecular dynamics simulations, which revealed the critical synergy of halogen and hydrogen bonding interactions in anion discrimination. In addition, the centrally located chiral (S)-BINOL motif of the [3] rotaxane axle component facilitates the complexed dicarboxylate species to be sensed via a fluorescence response.
publisher WILEY-V C H VERLAG GMBH
issn 1433-7851
year published 2018
volume 57
issue 2
beginning page 584
ending page 588
digital object identifier (doi) 10.1002/anie.201711176
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000419110500038
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journal analysis (jcr 2017):
journal impact factor 12.102
5 year journal impact factor 11.954
category normalized journal impact factor percentile 92.105
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