Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers
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
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Beilstein Journal of Organic ChemistryAuthors
Date
2019Discipline
Orgaaninen kemiaEpäorgaaninen ja analyyttinen kemiaOrganic ChemistryInorganic and Analytical ChemistryCopyright
© 2019 The Authors
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.
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Beilstein Institut zur Foerderung der Chemischen WissenschaftenISSN Search the Publication Forum
2195-951XKeywords
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https://www.beilstein-journals.org/bjoc/content/ supplementary/1860-5397-15-241-S1.pdfPublication in research information system
https://converis.jyu.fi/converis/portal/detail/Publication/33386349
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Academy of FinlandFunding program(s)
Research costs of Academy Research Fellow, AoF; Academy Research Fellow, AoF; Postdoctoral Researcher, AoF
Additional information about funding
We wish to thank The Academy of Finland (projects 284562, 278743 and 312514 to E.K. and 285855 to J.O.M.), the University of Jyväskylä and the Deutsche Forschungsgemeinschaft (Core Facility BioSupraMol) for financial support. J.O.M wishes to acknowledge Finnish Grid and Cloud Infrastructure (persistent identifier urn:nbn:fi:research-infras-2016072533), CSC - IT Center for Science, Finland, and Prof. Heikki M. Tuononen for computational resources.

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