6533b7dafe1ef96bd126e104
RESEARCH PRODUCT
Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers
Perdita E. BarranAnniina KiesiläAnneli KruveJani O. MoilanenElina KaleniusChristoph A. Schalleysubject
Cation bindingmassaspektrometriaanionitDimerpyridinearenes010402 general chemistryDFT calculations01 natural sciencesFull Research Paperdft calculationsIonlcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistryPolymer chemistryPyridinesupramolekulaarinen kemiaresorcinarenesInfrared multiphoton dissociationcation bindingAnion bindinglcsh:Science010405 organic chemistryChemistrytiheysfunktionaaliteoriaOrganic ChemistryCationic polymerizationkationit5470104 chemical sciences3. Good healthChemistryion mobility mass spectrometrymacrocycleslcsh:Qdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-10-01 | Beilstein Journal of Organic Chemistry |