A Potent Halogen‐Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis. Issue 39 (19th August 2019)

• Record Type: Journal Article
• Authors: Bunchuay, Thanthapatra; Docker, Andrew; Martinez‐Martinez, Antonio J.; Beer, Paul D.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 39(2019)
• Page Start: 13823
• Page End: 13827
• Publication Date: 2019-08-19
• Subjects: anion recognition -- halogen bonding -- rotaxanes -- supramolecular chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201907625
• Languages: English
• ISSNs: 1433-7851

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 : The covalent appendage of electron deficient perfluoroaryl substituents to a bis‐iodotriazole pyridinium group produces a powerful halogen bond donor for anion recognition. Using this motif, halogen bonding anion templation is demonstrated as a highly efficient method for constructing a rotaxane in near quantitative yield, capable of strong halide binding in 50 % water‐containing aqueous media.