ArticleJournal of the American Chemical Society2022
Reversible Capture and Release of a Ligand Mediated by a Long-Range Relayed Polarity Switch in a Urea Oligomer.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Hydrogen Bonding within DynamicJournal of the American Chemical Society · 2026Article
- Multiple hydrogen-bonded dimers: are only the frontier atoms relevant?Physical chemistry chemical physics : PCCP · 2024Article
- Anion-Dependent Hydrogen-Bond Polarity Switching in Ethylene-bridged Urea Oligomers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Chemically Fueled Communication Along a Scaffolded Nanoscale Array of Squaramides.Angewandte Chemie (International ed. in English) · 2023Article
- Dynamic and Persistent Cyclochirality in Hydrogen-Bonded Derivatives of Medium-Ring Triamines.Journal of the American Chemical Society · 2023Article
- Conformational preference in difluoroacetamide oligomers: probing the potential for foldamers with C-H⋯O hydrogen bonds.Organic & biomolecular chemistry · 2023Article
- Switching imidazole reactivity by dynamic control of tautomer state in an allosteric foldamer.Nature communications · 2023Article
- Screw sense and screw sensibility: communicating information by conformational switching in helical oligomers.Chemical Society reviews · 2023Review
- Proton transfer network with luminescence display controls OFF/ON catalysis that generates a high-speed slider-on-deck.RSC advances · 2023Article
- A ChiralJournal of the American Chemical Society · 2022Article
- Supramolecular interactions between ethylene-bridged oligoureas: nanorings and chains formed by cooperative positive allostery.Chemical science · 2022Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
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.
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Registered trials
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