Anion-Dependent Hydrogen-Bond Polarity Switching in Ethylene-bridged Urea Oligomers

David P Tilly, David T J Morris, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

1 Citation (Scopus)


The reversible coordination of anions to an N,N’-
disubstituted 3,5-bis(trifluoromethyl)phenylurea located at a terminus
of a linear chain of ethylene-bridged hydrogen-bonded ureas triggers
a cascade of conformational changes. A series of hydrogen-bond
polarity reversals propagates along the oligomer, leading to a global
switch of its hydrogen-bond directionality. The induced polarity switch,
transmitted through four reversible urea groups, results in a change
in emission and excitation wavelengths of a fluorophore located at the
opposite terminus of the oligomer. The molecule thus behaves as a
chemical sensor with a relayed remote spectroscopic response to
variations in anion concentration. The polarity switch induced by anion
concentration constitutes an artificial communication mechanism for
conveying information through oligomeric structures.
Original languageEnglish
Article numbere202302210
JournalChemistry – A European Journal
Issue number62
Early online date17 Aug 2023
Publication statusE-pub ahead of print - 17 Aug 2023

Bibliographical note

Funding Information:
We acknowledge funding from the European Research Council through Advanced Grant 883786 (DOGMATRON), the European Commission through a Marie Sklodowska Curie fellowship HORIZON 2020 (grant REFOLDAMER) to D.P.T. and the Leverhulme Trust, the EPSRC through the Bristol Chemical Synthesis Centre for Doctoral Training EP/L015366/1 (studentship to D.T.J.M.).

Publisher Copyright:
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Structured keywords

  • BCS and TECS CDTs


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