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A Potent Halogen‐Bonding Donor Motif for Anion Recognition and Anion Template Mechanical Bond Synthesis
Author(s) -
Bunchuay Thanthapatra,
Docker Andrew,
MartinezMartinez Antonio J.,
Beer Paul D.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201907625
Subject(s) - rotaxane , halogen bond , chemistry , hydrogen bond , pyridinium , covalent bond , molecule , aqueous solution , intramolecular force , halogen , molecular recognition , combinatorial chemistry , crystallography , stereochemistry , supramolecular chemistry , photochemistry , alkyl , organic chemistry
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.