A1 Journal article (refereed)
Oligoamide Foldamers as Helical Chloride Receptors : the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions (2019)
Helttunen, K., Annala, R., Suhonen, A., Iloniemi, J., Kalenius, E., Aragay, G., Ballester, P., Tuononen, H., & Nissinen, M. (2019). Oligoamide Foldamers as Helical Chloride Receptors : the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions. Chemistry : An Asian Journal, 14(5), 647-654. https://doi.org/10.1002/asia.201801869
JYU authors or editors
Publication details
All authors or editors: Helttunen, Kaisa; Annala, Riia; Suhonen, Aku; Iloniemi, Juho; Kalenius, Elina; Aragay, Gemma; Ballester, Pablo; Tuononen, Heikki; Nissinen, Maija
Journal or series: Chemistry : An Asian Journal
ISSN: 1861-4728
eISSN: 1861-471X
Publication year: 2019
Volume: 14
Issue number: 5
Pages range: 647-654
Publisher: Wiley - VCH Verlag GmbH & Co. KGaA
Publication country: Germany
Publication language: English
DOI: https://doi.org/10.1002/asia.201801869
Publication open access: Not open
Publication channel open access:
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/63409
Abstract
The anion‐binding properties of three closely related oligoamide foldamers were studied using NMR spectroscopy, isothermal titration calorimetry and mass spectrometry, as well as DFT calculations. The 1H NMR spectra of the foldamers in [D6]acetone solution revealed partial preorganization by intramolecular hydrogen bonding, which creates a suitable cavity for anion binding. The limited size of the cavity, however, enabled efficient binding by the inner amide protons only for the chloride anion resulting in the formation of a thermodynamically stable 1:1 complex. All 1:1 chloride complexes displayed a significant favourable contribution of the entropy term. Most likely, this is due to the release of ordered solvent molecules solvating the free foldamer and the anion to the bulk solution upon complex formation. The introduction of electron‐withdrawing substituents in foldamers 2 and 3 had only a slight effect on the thermodynamic constants for chloride binding compared to the parent receptor. Remarkably, the binding of chloride to foldamer 3 not only produced the expected 1:1 complex but also open aggregates with 1:2 (host:anion) stoichiometry.
Keywords: supramolecular chemistry; anions
Free keywords: receptors; host-guest systems; foldamers
Contributing organizations
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Ministry reporting: Yes
VIRTA submission year: 2019
JUFO rating: 1