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Extended cavitands of nanoscale dimensions

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dc.contributor.authorMenozzi, Edoardo
dc.contributor.authorOnagi, Hideki
dc.contributor.authorRheingold, Arnold L
dc.contributor.authorRebek, Julius (Jr.)
dc.date.accessioned2015-12-08T22:26:37Z
dc.date.issued2005
dc.date.updated2015-12-08T09:12:49Z
dc.description.abstractNew 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.
dc.identifier.issn1434-193X
dc.identifier.urihttp://hdl.handle.net/1885/33705
dc.publisherWiley-VCH Verlag GMBH
dc.sourceEuropean Journal of Organic Chemistry
dc.subjectKeywords: Cavitands; Host-guest systems; Supramolecular chemistry
dc.titleExtended cavitands of nanoscale dimensions
dc.typeJournal article
local.bibliographicCitation.lastpage3636
local.bibliographicCitation.startpage3633
local.contributor.affiliationMenozzi, Edoardo, Scripps Research Institute
local.contributor.affiliationOnagi, Hideki, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationRheingold, Arnold L, University of California
local.contributor.affiliationRebek, Julius (Jr.), Scripps Research Institute
local.contributor.authoruidOnagi, Hideki, u9718356
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor100799 - Nanotechnology not elsewhere classified
local.identifier.ariespublicationu4005981xPUB105
local.identifier.citationvolume2005/17
local.identifier.doi10.1002/ejoc.200500342
local.identifier.scopusID2-s2.0-25144438552
local.type.statusPublished Version

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