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http://hdl.handle.net/10261/212897
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Campo DC | Valor | Lengua/Idioma |
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dc.contributor.author | Altieri, Andrea | es_ES |
dc.contributor.author | Aucagne, Vincent | es_ES |
dc.contributor.author | Carrillo Fumero, Romen | es_ES |
dc.contributor.author | Clarkson, Guy J. | es_ES |
dc.contributor.author | D'Souza, Daniel M. | es_ES |
dc.contributor.author | Dunnett, Jennifer A. | es_ES |
dc.contributor.author | Leigh, David A. | es_ES |
dc.contributor.author | Mullen, Kathleen M. | es_ES |
dc.date.accessioned | 2020-06-01T13:52:38Z | - |
dc.date.available | 2020-06-01T13:52:38Z | - |
dc.date.issued | 2011-07-14 | - |
dc.identifier.citation | Chemical science 2(10): 1922-1928 (2011) | es_ES |
dc.identifier.issn | 2041-6520 | - |
dc.identifier.uri | http://hdl.handle.net/10261/212897 | - |
dc.description.abstract | We report on the synthesis, structure and properties of [2]rotaxanes prepared by the assembly of benzylic amide macrocycles around a series of amide and sulfide-/sulfoxide-/sulfone-containing threads. The efficacy of rotaxane formation is related to the hydrogen bond accepting properties of the various sulfur-containing functional groups in the thread, with the highest yields (up to 63% with a rigid vinyl spacer in the template site) obtained for sulfoxide rotaxanes. X-Ray crystallography of a sulfoxide rotaxane, 5, shows that the macrocycle adopts a highly symmetrical chair-like conformation in the solid state, with short hydrogen bonds between the macrocycle isophthalamide NH-protons and the amide carbonyl and sulfoxide S–O of the thread. In contrast, in the X-ray crystal structures of the analogous sulfide (4) and sulfone (6) rotaxanes, the macrocycle adopts boat-like conformations with long intercomponent NH⋯O[double bond, length as m-dash]SO and NH⋯S hydrogen bonds (in addition to several intercomponent amide–amide hydrogen bonds). Taking advantage of the different hydrogen bonding modes of the sulfur-based functional groups, a switchable molecular shuttle was prepared in which the oxidation level of sulfur determines the position of the macrocycle on the thread. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Royal Society of Chemistry (UK) | es_ES |
dc.relation.isversionof | Postprint | es_ES |
dc.rights | closedAccess | es_ES |
dc.subject | [2]rotaxanes | es_ES |
dc.subject | Sulfur-containing | es_ES |
dc.subject | Shuttles | es_ES |
dc.title | Sulfur-containing amide-based [2]rotaxanes and molecular shuttles | es_ES |
dc.type | artículo | es_ES |
dc.identifier.doi | 10.1039/C1SC00335F | - |
dc.description.peerreviewed | Peer reviewed | es_ES |
dc.relation.publisherversion | https://doi.org/10.1039/C1SC00335F | es_ES |
dc.identifier.e-issn | 2041-6539 | - |
dc.rights.license | https://creativecommons.org/licenses/by/4.0/ | es_ES |
dc.contributor.funder | Engineering and Physical Sciences Research Council (UK) | es_ES |
dc.contributor.funder | Fundación Ramón Areces | es_ES |
dc.relation.csic | No | es_ES |
oprm.item.hasRevision | no ko 0 false | * |
dc.identifier.funder | http://dx.doi.org/10.13039/501100000266 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/100008054 | es_ES |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.languageiso639-1 | en | - |
item.fulltext | No Fulltext | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.cerifentitytype | Publications | - |
item.grantfulltext | none | - |
item.openairetype | artículo | - |
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accesoRestringido.pdf | Artículo principal | 16,34 kB | Adobe PDF | Visualizar/Abrir |
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