Simultaneous selective recognition of two different anions within a hydrogen/halogen bonding cage
- 1Research School of Chemistry
- 2Australian National University
Abstract
The search for selective anion receptors that can function in water is a longstanding challenge in supramolecular chemistry, motivated by anions’ fundamental roles (and potential applications) in biological, environmental and industrial processes. Here we incorporate halogen and hydrogen bond donors into an easy-toprepare organic cage molecule and demonstrate that this can bind anions at either or both of a halogen bonding pocket and hydrogen bonding pockets depending on the nature of the anions and the solvent. The halogen bonding pocket comprised of six bromopyridinium donors is a potent host for iodide anions, and can selectively bind this guest in water as strongly as biological iodide binders ( K a = 43,000 M –1 measured by 1 H NMR spectroscopy) with the exclusion of other halide anions. In DMSO/water mixtures, the hydrogen bonding pockets are able to recognise chloride anions, resulting in the formation of well-defined mixed anion iodide/chloride complexes with an iodide bound in the centre of the cage and chlorides in the peripheral binding sites. This demonstrates the exquisite selectivity afforded by halogen bonding systems and reveals a general route to a range of supramolecular anion hosts that bind multiple guests in different locations.
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BibTeX
@misc{smith2026simultaneous,
title = {{Simultaneous selective recognition of two different anions within a hydrogen/halogen bonding cage}},
author = {Bailee R. Smith and Rosemary J. Goodwin and Nicholas G. White},
howpublished = {ChemRxiv},
year = {2026},
month = sep,
doi = {10.26434/chemrxiv.15004776/v2},
url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15004776/v2},
note = {CC BY-NC-ND},
}
RIS
TY - UNPB
TI - Simultaneous selective recognition of two different anions within a hydrogen/halogen bonding cage
AU - Bailee R. Smith
AU - Rosemary J. Goodwin
AU - Nicholas G. White
PY - 2026
DA - 2026/09/28
PB - ChemRxiv
DO - 10.26434/chemrxiv.15004776/v2
UR - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15004776/v2
AB - The search for selective anion receptors that can function in water is a longstanding challenge in supramolecular chemistry, motivated by anions’ fundamental roles (and potential applications) in biological, environmental and industrial processes. Here we incorporate halogen and hydrogen bond donors into an easy-toprepare organic cage molecule and demonstrate that this can bind anions at either or both of a halogen bonding pocket and hydrogen bonding pockets depending on the nature of the anions and the solvent. The halogen bonding pocket comprised of six bromopyridinium donors is a potent host for iodide anions, and can selectively bind this guest in water as strongly as biological iodide binders ( K a = 43,000 M –1 measured by 1 H NMR spectroscopy) with the exclusion of other halide anions. In DMSO/water mixtures, the hydrogen bonding pockets are able to recognise chloride anions, resulting in the formation of well-defined mixed anion iodide/chloride complexes with an iodide bound in the centre of the cage and chlorides in the peripheral binding sites. This demonstrates the exquisite selectivity afforded by halogen bonding systems and reveals a general route to a range of supramolecular anion hosts that bind multiple guests in different locations.
ER -