Please use this identifier to cite or link to this item:
http://hdl.handle.net/10773/20329
Title: | Selective Nitrate Recognition by a Halogen-Bonding Four-Station [3]Rotaxane Molecular Shuttle |
Author: | Barendt, Timothy A. Docker, Andrew Marques, Igor Felix, Vitor Beer, Paul D. |
Keywords: | AQUEOUS SOLVENT MIXTURES ANION RECOGNITION SUPRAMOLECULAR CHEMISTRY DYNAMICS SIMULATIONS HYDROGEN-BONDS RECEPTOR BINDING ROTAXANE PREORGANIZATION AMBER |
Issue Date: | 2016 |
Publisher: | WILEY-V C H VERLAG GMBH |
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. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/20329 |
DOI: | 10.1002/anie.201604327 |
ISSN: | 1433-7851 |
Publisher Version: | 10.1002/anie.201604327 |
Appears in Collections: | CICECO - Artigos |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Selective Nitrate Recognition by a Halogen-Bonding Four-Station [3]Rotaxane Molecular Shuttle_10.1002anie.201604327.pdf | 3.52 MB | Adobe PDF |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.