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Tetraurea macrocycles: aggregation-driven binding of chloride in aqueous solutions

preprint
revised on 21.02.2019, 22:30 and posted on 22.02.2019, 16:26 by Xin Wu, Patrick Wang, Peter Turner, William Lewis, Osman Catal, Donald Thomas, Philip Gale

Artificial receptors that recognise anionic species vianoncovalent 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 (> 105M-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 viaintermolecular hydrogen bonds and aromatic stacking. In aqueous solutions, macrocycle aggregation generates hydrophobic and size-selective binding pockets favourable for hydrogen bonding with chloride. As a result, micromolar affinity and highly selective chloride binding has been achieved with this simple small molecule (MW < 700) in 60 vol% water/acetonitrile.

Funding

Selective anion transporters with therapeutic potential

Australian Research Council

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History

Email Address of Submitting Author

philip.gale@sydney.edu.au

Institution

University of Sydney

Country

Australia

ORCID For Submitting Author

0000-0001-9751-4910

Declaration of Conflict of Interest

None

Exports