Tetraurea Macrocycles: Aggregation-Driven Binding of Chloride in Aqueous Solutions
Access status:
Open Access
Type
ArticleAuthor/s
Wu, XinWang, Patrick
Turner, Peter
Lewis, William
Catal, Osman
Thomas, Donald S.
Gale, Philip A.
Abstract
Artificial receptors that recognize anionic species via non-covalent interactions have a wide range of biomedical, industrial, and environmental applications. A major challenge in this area of research is to achieve high-affinity and selective anion binding in aqueous media. So ...
See moreArtificial receptors that recognize anionic species via non-covalent interactions have a wide range of biomedical, industrial, and environmental applications. A major challenge in this area of research is to achieve high-affinity and selective anion binding in aqueous media. So far, only a few examples of receptors capable of strong (>105 M 1) anion binding in solutions containing >50% water are available, and none show selectivity for chloride. We report here the discovery of a D4h-symmetric fluorinated tetraurea macrocycle that fulfils this function owing to its unique self-assembly properties. The macrocycle has a strong tendency to self-associate into columnar aggregates via intermolecular hydrogen bonds and aromatic stacking. In aqueous solutions, macrocycle aggregation generates solvent-shielding and size-selective binding pockets favorable for hydrogen bonding with chloride. As a result, micromolar affinity and highly selective chloride binding have been achieved with this simple small molecule (MW < 700) in 60 vol % water/acetonitrile.
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See moreArtificial receptors that recognize anionic species via non-covalent interactions have a wide range of biomedical, industrial, and environmental applications. A major challenge in this area of research is to achieve high-affinity and selective anion binding in aqueous media. So far, only a few examples of receptors capable of strong (>105 M 1) anion binding in solutions containing >50% water are available, and none show selectivity for chloride. We report here the discovery of a D4h-symmetric fluorinated tetraurea macrocycle that fulfils this function owing to its unique self-assembly properties. The macrocycle has a strong tendency to self-associate into columnar aggregates via intermolecular hydrogen bonds and aromatic stacking. In aqueous solutions, macrocycle aggregation generates solvent-shielding and size-selective binding pockets favorable for hydrogen bonding with chloride. As a result, micromolar affinity and highly selective chloride binding have been achieved with this simple small molecule (MW < 700) in 60 vol % water/acetonitrile.
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Date
2019-05-09Publisher
Cell PressCitation
Chem 2019, 5, 1210–1222Share