Journal article
Reversible Capture and Release of a Ligand Mediated by a Long-Range Relayed Polarity Switch in a Urea Oligomer
Journal of the American Chemical Society, Vol.144(7), pp.2841-2846
2022
PMID: 35142216
Abstract
Ethylene-bridged oligoureas characterized by a continuous, switchable chain of hydrogen bonds and carrying a binding site (an N,N'-disubstituted urea) for a hydrogen-bond-accepting ligand (a phosphine oxide) were synthesized. These oligomers show stronger ligand binding when the binding site is located at the hydrogen-bond-donating terminus than when the same binding site is at the hydrogen-bond-accepting terminus. An acidic group at the terminus remote from the binding site allows hydrogen bond polarity, and hence ligand binding ability, to be controlled remotely by a deprotonation/reprotonation cycle. Addition of base induces a remote conformational change that is relayed through up to five urea linkages, reducing the ability of the binding site to retain an intermolecular association to its ligand, which is consequently released into solution. Reprotonation returns the polarity of the oligomer to its original directionality, restoring the function of the remote binding site, which consequently recaptures the ligand. This is the first example of a synthetic molecular structure that relays intermolecular binding information, and these "dynamic foldamer" structures are prototypes of components for chemical systems capable of controlling chemical function from a distance.
Details
- Title
- Reversible Capture and Release of a Ligand Mediated by a Long-Range Relayed Polarity Switch in a Urea Oligomer
- Authors
- Steven M. Wales (Author) - University of BristolDavid T. J. Morris (Author) - University of BristolJonathan Clayden (Corresponding Author) - University of Bristol
- Publication details
- Journal of the American Chemical Society, Vol.144(7), pp.2841-2846
- Publisher
- American Chemical Society
- DOI
- 10.1021/jacs.1c11928
- ISSN
- 1520-5126
- PMID
- 35142216
- Organisation Unit
- Student Services and Engagement; School of Science, Technology and Engineering
- Language
- English
- Record Identifier
- 99707363702621
- Output Type
- Journal article
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- Chemistry, Multidisciplinary
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