Selective Nitrate Recognition by a Halogen-Bonding Four-Station [3]Rotaxane Molecular Shuttle
authors Barendt, TA; Docker, A; Marques, I; Felix, V; Beer, PD
nationality International
journal ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
author keywords halogen bonding; molecular devices; molecular dynamics; rotaxanes; supramolecular chemistry
keywords AQUEOUS SOLVENT MIXTURES; ANION RECOGNITION; SUPRAMOLECULAR CHEMISTRY; DYNAMICS SIMULATIONS; HYDROGEN-BONDS; RECEPTOR; BINDING; ROTAXANE; PREORGANIZATION; AMBER
abstract The synthesis of the first halogen bonding [3]rotaxane host system containing a bis-iodo triazolium-bis-naphthalene diimide four station axle component is reported. Proton NMR anion binding titration experiments revealed the halogen bonding rotaxane is selective for nitrate over the more basic acetate, hydrogen carbonate and dihydrogen phosphate oxoanions and chloride, and exhibits enhanced recognition of anions relative to a hydrogen bonding analogue. This elaborate interlocked anion receptor functions via a novel dynamic pincer mechanism where upon nitrate anion binding, both macrocycles shuttle from the naphthalene diimide stations at the periphery of the axle to the central halogen bonding iodo-triazolium station anion recognition sites to form a unique 1:1 stoichiometric nitrate anion-rotaxane sandwich complex. Molecular dynamics simulations carried out on the nitrate and chloride halogen bonding [3]rotaxane complexes corroborate the (HNMR)-H-1 anion binding results.
publisher WILEY-V C H VERLAG GMBH
issn 1433-7851
year published 2016
volume 55
issue 37
beginning page 11069
ending page 11076
digital object identifier (doi) 10.1002/anie.201604327
web of science category Chemistry, Multidisciplinary
subject category Chemistry
unique article identifier WOS:000383642300017
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journal impact factor 12.102
5 year journal impact factor 11.954
category normalized journal impact factor percentile 92.105
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