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A Chiral Halogen‐Bonding [3]Rotaxane for the Recognition and Sensing of Biologically Relevant Dicarboxylate Anions
Author(s) -
Lim Jason Y. C.,
Marques Igor,
Félix Vítor,
Beer Paul D.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711176
Subject(s) - rotaxane , halogen bond , hydrogen bond , chemistry , molecular recognition , halogen , ion , chloride , molecule , stoichiometry , fluorescence , polymer chemistry , stereochemistry , photochemistry , combinatorial chemistry , supramolecular chemistry , organic chemistry , alkyl , physics , quantum mechanics
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.