Extended cavitands of nanoscale dimensions
Date
2005
Authors
Menozzi, Edoardo
Onagi, Hideki
Rheingold, Arnold L
Rebek, Julius (Jr.)
Journal Title
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Volume Title
Publisher
Wiley-VCH Verlag GMBH
Abstract
New tetrabenzimidazole cavitands with upper rims extended by aromatic groups have been prepared and their X-ray structures were analyzed. The reversible encapsulation of a series of n-alkylammonium guests was studied by NMR spectroscopy and mass spectrometry. These guests showed different binding modes and unique interactions with the hydrophobic cavity. The trimethylammonium guests bearing n-butyl to n-hexyl substituents stabilize the C4v conformation of the cavitand by additional CH⋯π interactions with the aromatic upper part. The longest n-hexylammonium salt adopts a minimal gauche conformation to fit in the cavity.
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Keywords
Keywords: Cavitands; Host-guest systems; Supramolecular chemistry
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Source
European Journal of Organic Chemistry
Type
Journal article
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Restricted until
2037-12-31
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