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

Beilstein Journal of Organic Chemistry

Elina Kalenius¹  Jani O. Moilanen¹  Anniina Kiesilä¹  Anneli Kruve²  Christoph A. Schalley²  Perdita Barran³ 

[1] Department of Chemistry, Nanoscience Center, University of Jyväskylä, P.O. Box 35, University of Jyväskylä, Finland;Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany;Michael Barber Centre for Collaborative Mass Spectrometry, Manchester Institute of Biotechnology, School of Chemistry, The University of Manchester, Princess Street, Manchester, UK;

关键词: cation binding;    dft calculations;    ion mobility mass spectrometry;    macrocycles;    pyridinearenes;    resorcinarenes;   

DOI  :  10.3762/bjoc.15.241

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown