263
Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

A. Kiesilä, J. O. Moilanen, A. Kruve, C. A. Schalley, P. Barran, E. Kalenius – 2019

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 these earlier results. 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.

Title
263
Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers
Author
A. Kiesilä, J. O. Moilanen, A. Kruve, C. A. Schalley, P. Barran, E. Kalenius
Date
2019-10-21
Identifier
DOI: 10.3762/bjoc.15.241
Citation
Beilstein J. Org. Chem.. 2019, 15, 2486-2492