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 editorsHelttunen, Kaisa; Annala, Riia; Suhonen, Aku; Iloniemi, Juho; Kalenius, Elina; Aragay, Gemma; Ballester, Pablo; Tuononen, Heikki; Nissinen, Maija

Journal or seriesChemistry : An Asian Journal

ISSN1861-4728

eISSN1861-471X

Publication year2019

Volume14

Issue number5

Pages range647-654

PublisherWiley - VCH Verlag GmbH & Co. KGaA

Publication countryGermany

Publication languageEnglish

DOIhttps://doi.org/10.1002/asia.201801869

Publication open accessNot 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.


Keywordssupramolecular chemistryanions

Free keywordsreceptors; host-guest systems; foldamers


Contributing organizations


Related projects


Ministry reportingYes

Reporting Year2019

JUFO rating1


Last updated on 2024-11-05 at 22:25