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Article: Dynamic chirality in donor-acceptor pretzelanes

TitleDynamic chirality in donor-acceptor pretzelanes
Authors
Issue Date2005
Citation
Journal of Organic Chemistry, 2005, v. 70, n. 23, p. 9334-9344 How to Cite?
AbstractA series of donor-acceptor pretzelanes has been synthesized, using self-assembly and template-directed protocols, and the dynamic processes that these pretzelanes undergo have been investigated in solution. These compounds exist as libraries of diastereoisomers as a result of their multiple Stereoelements, which are dynamically interconverted by several different, in some cases competing, processes. Altering the structure of the pretzelanes changes the rates and mechanisms by which these diastereoisomers equilibrate. Additionally, inserting an element of fixed chirality allows the equilibrium to be biased, while maintaining the barrier to the equilibration processes. These results bode well for the future construction of molecular devices based on switchable diastereoisomerism involving metastable states. © 2005 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/332636
ISSN
2023 Impact Factor: 3.3
2023 SCImago Journal Rankings: 0.724
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLiu, Y.-
dc.contributor.authorVignon, S. A.-
dc.contributor.authorZhang, X.-
dc.contributor.authorBonvallet, P. A.-
dc.contributor.authorKhan, S. I.-
dc.contributor.authorHouk, K. N.-
dc.contributor.authorStoddart, J. F.-
dc.date.accessioned2023-10-06T05:13:05Z-
dc.date.available2023-10-06T05:13:05Z-
dc.date.issued2005-
dc.identifier.citationJournal of Organic Chemistry, 2005, v. 70, n. 23, p. 9334-9344-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://hdl.handle.net/10722/332636-
dc.description.abstractA series of donor-acceptor pretzelanes has been synthesized, using self-assembly and template-directed protocols, and the dynamic processes that these pretzelanes undergo have been investigated in solution. These compounds exist as libraries of diastereoisomers as a result of their multiple Stereoelements, which are dynamically interconverted by several different, in some cases competing, processes. Altering the structure of the pretzelanes changes the rates and mechanisms by which these diastereoisomers equilibrate. Additionally, inserting an element of fixed chirality allows the equilibrium to be biased, while maintaining the barrier to the equilibration processes. These results bode well for the future construction of molecular devices based on switchable diastereoisomerism involving metastable states. © 2005 American Chemical Society.-
dc.languageeng-
dc.relation.ispartofJournal of Organic Chemistry-
dc.titleDynamic chirality in donor-acceptor pretzelanes-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/jo051430g-
dc.identifier.scopuseid_2-s2.0-27744491286-
dc.identifier.volume70-
dc.identifier.issue23-
dc.identifier.spage9334-
dc.identifier.epage9344-
dc.identifier.isiWOS:000233209400029-

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