A1 Journal article (refereed)
Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers (2019)

Kiesilä, A., Moilanen, J. O., Kruve, Anneli., Schalley, C. A., Barran, P., & Kalenius, E. (2019). Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers. Beilstein Journal of Organic Chemistry, 15, 2486-2492. https://doi.org/10.3762/bjoc.15.241

JYU authors or editors

Publication details

All authors or editors: Kiesilä, Anniina; Moilanen, Jani O.; Kruve, Anneli.; Schalley, Christoph A.; Barran, Perdita; Kalenius, Elina

Journal or series: Beilstein Journal of Organic Chemistry

ISSN: 2195-951X

eISSN: 1860-5397

Publication year: 2019

Volume: 15

Pages range: 2486–2492

Publisher: Beilstein Institut zur Foerderung der Chemischen Wissenschaften

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.3762/bjoc.15.241

Research data link: https://www.beilstein-journals.org/bjoc/content/ supplementary/1860-5397-15-241-S1.pdf

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/66183

Abstract

Pyridine[4]arenes have previously been considered as anion binding hosts due to the electron-poor nature of the pyridine ring. Herein, we demonstrate the encapsulation of Me4N+ cations inside a dimeric hydrogen-bonded pyridine[4]arene capsule, which contradicts with earlier assumptions. The complexation of a cationic guest inside the pyridine[4]arene dimer has been detected and studied by multiple gas-phase techniques, ESI-QTOF-MS, IRMPD, and DT-IMMS experiments, as well as DFT calculations. The comparison of classical resorcinarenes with pyridinearenes by MS and NMR experiments reveals clear differences in their host–guest chemistry and implies that cation encapsulation in pyridine[4]arene is an anion-driven process.

Keywords: supramolecular chemistry; anions; cations; density functional theory; mass spectrometry

Free keywords: cation binding; DFT calculations; ion mobility mass spectrometry; macrocycles; pyridinearenes; resorcinarenes

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Ministry reporting: Yes

Reporting Year: 2019

JUFO rating: 1