ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
v3.pdf (8.65 MB)
0/0

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

preprint
revised on 21.02.2019 and posted on 22.02.2019 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

Find out more...

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