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http://hdl.handle.net/10773/20608
Title: | Increased Halide Recognition Strength by Enhanced Intercomponent Preorganisation in Triazolium Containing [2] Rotaxanes |
Author: | White, Nicholas G. Costa, Paulo J. Carvalho, Silvia Felix, Vitor Beer, Paul D. |
Keywords: | ANION RECOGNITION HYDROGEN-BONDS MACROCYCLIC RECEPTOR COMPUTER-PROGRAM TERMINAL ALKYNES AQUEOUS-MEDIA ARYL-TRIAZOLE BINDING CHLORIDE COMPLEXES |
Issue Date: | 2013 |
Publisher: | WILEY-V C H VERLAG GMBH |
Abstract: | Three triazolium-based [2]rotaxanes containing different sized axle and macrocycle components were synthesised in good yields (40-57%) through chloride anion templation. The anion recognition properties of the interlocked receptor systems were investigated using (HNMR)-H-1 titration experiments: all three rotaxanes display impressive selectivities for halide anions over the more basic oxoanion acetate. The rotaxanes incorporating shorter, more rigid axle components with aryl-substituted triazolium groups display substantially higher anion binding affinities than those with longer, bis-alkyl-substituted heterocycles, which is attributed to the increased intercomponent preorganisation afforded by the smaller axle component. Computational DFT and molecular dynamics simulations composed of unconstrained and umbrella sampling simulations corroborate the experimental observations. |
Peer review: | yes |
URI: | http://hdl.handle.net/10773/20608 |
DOI: | 10.1002/chem.201303122 |
ISSN: | 0947-6539 |
Publisher Version: | 10.1002/chem.201303122 |
Appears in Collections: | CICECO - Artigos |
Files in This Item:
File | Description | Size | Format | |
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Increased Halide Recognition Strength by Enhanced Intercomponent Preorganisation in Triazolium Containing [2]Rotaxanes_10.1002chem.201303122.pdf | 1.91 MB | Adobe PDF |
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