Competing Hydrogen-Bond Polarities in a Dynamic Oligourea Foldamer: A Molecular Spring Torsion Balance

Romina Wechsel, Matej Žabka, John W. Ward, Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

16 Citations (Scopus)
227 Downloads (Pure)

Abstract

Symmetrical oligourea foldamers were made from meso cyclohexane-1,2-diamine and desymmetrised by incorporating terminal functional groups (carbamates, ureas or thioureas) with differing hydrogen-bonding capacities. Irrespective of solvent, the foldamers populate a dynamic equilibrium of two alternative screw-sense conformers whose relative population is determined by the competing hydrogen-bonding properties of the terminal groups, dictating the foldamer's global hydrogen-bond directionality. Intermolecular association of these dynamic foldamers with achiral anionic guests (acetate or phosphate, but not neutral hydrogen-bonding solvents) leads to inversion of the conformational preference, as strong intermolecular hydrogen bonding induces reorganization of the intramolecular hydrogen-bond network. The foldamers behave as a molecular torsion balance whose conformational preference is governed by competing hydrogen-bond pairing.

Original languageEnglish
Pages (from-to)3528-3531
Number of pages4
JournalJournal of the American Chemical Society
Volume140
Issue number10
Early online date1 Mar 2018
DOIs
Publication statusPublished - 14 Mar 2018

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