Title:
Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers
Author(s):
Kiesilä, Anniina; Moilanen, Jani O.; Kruve, Anneli; Schalley, Christoph A.; Barran, Perdita; Kalenius, Elina
Year of publication:
2019
Available Date:
2019-10-31T11:24:43Z
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.
Part of Identifier:
e-ISSN (online): 1860-5397
Keywords:
cation binding
DFT calculations
ion mobility mass spectrometry
macrocycles
pyridinearenes
resorcinarenes
DDC-Classification:
547 Organische Chemie
Publication Type:
Wissenschaftlicher Artikel
URL of the Original Publication:
DOI of the Original Publication:
Journaltitle:
Beilstein journal of organic chemistry
Department/institution:
Biologie, Chemie, Pharmazie
Institut für Chemie und Biochemie / Organische Chemie