A Potent Halogen‐Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis. (19th August 2019)

• Record Type: Journal Article
• Authors: Bunchuay, Thanthapatra; Docker, Andrew; Martinez‐Martinez, Antonio J.; Beer, Paul D.
• Is Part Of: Angewandte Chemie. Volume 131:Number 39(2019)
• Page Start: 13961
• Page End: 13965
• Publication Date: 2019-08-19
• Subjects: Anionenerkennung -- Halogenbindungen -- Rotaxane -- Supramolekulare Chemie; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201907625
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: The covalent attachment of electron deficient perfluoroaryl substituents to a bis‐iodotriazole pyridinium group produces a remarkably potent halogen bonding donor motif for anion recognition in aqueous media. Such a motif also establishes halogen bonding anion templation as a highly efficient method for constructing a mechanically interlocked molecule in unprecedented near quantitative yield. The resulting bis‐perfluoroaryl substituted iodotriazole pyridinium axle containing halogen bonding [2]rotaxane host exhibits exceptionally strong halide binding affinities in competitive 50 % water containing aqueous media, by a factor of at least three orders of magnitude greater in comparison to a hydrogen bonding rotaxane host analogue. These observations further champion and advance halogen bonding as a powerful tool for recognizing anions in aqueous media. Abstract : Das kovalente Anhängsel von elektronenarmen Perfluorarylsubstituenten an einer Bisiodtriazolpyridiniumgruppe erzeugt einen starken Halogenbrückendonor für die Anionenerkennung. Mit diesem Motiv wird die Halogenbrücken‐Anionen‐Templation als hocheffizientes Verfahren zur Herstellung eines Rotaxans in nahezu quantitativer Ausbeute demonstriert, das in der Lage ist, Halogenidionen in Medien mit 50 % Wasser stark zu binden.