Beilstein J. Org. Chem.2019,15, 2486–2492, doi:10.3762/bjoc.15.241
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.
Keywords: cation binding; DFT calculations; ion mobility mass spectrometry; macrocycles; pyridinearenes; resorcinarenes; Introduction
Resorcinarenes and their derivatives are known for the molecular recognition properties of their self-assembled
dimeric and hexameric capsules, which can encapsulate cationic and neutral guests [1][2][3]. Pyridine[4]arenes [4] are analogous macrocycles to resorcin[4]arenes. Whereas resorcinarenes are cyclic tetramers of resorcinol, pyridinearenes are formed from 2,6-dihydroxypyridine (see Scheme 1). Although the
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Graphical Abstract
Scheme 1:
Structures of tetraisobutylpyridine[4]arene 1 and tetraisobutylresorcin[4]arene 2.