A Chiral Halogen-Bonding [3]Rotaxane for the Recognition and Sensing of Biologically Relevant Dicarboxylate Anions.

Authors :: Lim JYC
Marques I
Félix V
Beer PD
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2018 Jan 08; Vol. 57 (2), pp. 584-588. Date of Electronic Publication: 2017 Dec 08.
Publication Year :: 2018
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.<br /> (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Anions chemistry
Chlorides chemistry
Hydrogen Bonding
Molecular Dynamics Simulation
Molecular Structure
Proton Magnetic Resonance Spectroscopy
Spectrometry, Fluorescence
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
Dicarboxylic Acids chemistry
Halogens chemistry
Rotaxanes chemistry

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