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Double protonation of a cis-Bipyridoallenophane detected via Chiral-Sensing Switch: the role of Ion Pairs

dc.contributor.authorCastro Fernandez, Sílvia 
dc.contributor.authorAlvarez Garcia, Jonathan 
dc.contributor.authorGarcía Río, Luis
dc.contributor.authorSilva López, Carlos 
dc.contributor.authorCid Fernández, María Magdalena 
dc.date.accessioned2024-01-24T08:49:59Z
dc.date.available2024-01-24T08:49:59Z
dc.date.issued2019-07-22
dc.identifier.citationOrganic Letters, 21(15): 5898-5902 (2019)spa
dc.identifier.issn15237060
dc.identifier.issn15237052
dc.identifier.urihttp://hdl.handle.net/11093/5777
dc.description.abstractWe prove that the confinement of the conformational space of pyridoallenophanes leads to intense chiroptical responses. Unlike the cyclic dimer [142], single-conformation [141]pyridoallenophanes isomerize under thermal and photochemical conditions. Yet, less-strained [141]-bipyridoallenophanes are stable and are prepared successfully. They, unexpectedly, undergo double protonation as a result of cooperative ion-pairing and hydrogen bonding. The complex formation forces a single configuration of the axis connecting both pyridyl rings recognized by a diagnostic circular dichroism (CD) signal at 330 nm.spa
dc.description.sponsorshipAgencia Estatal de Investigación | Ref. CTQ2017-84354-Pspa
dc.description.sponsorshipAgencia Estatal de Investigación | Ref. CTQ2017-85919-Rspa
dc.description.sponsorshipXunta de Galicia | Ref. IN607C 2016/03spa
dc.description.sponsorshipXunta de Galicia | Ref. ED431C 2017/70spa
dc.description.sponsorshipXunta de Galicia | Ref. Ref. ED431G/09spa
dc.language.isoengspa
dc.publisherOrganic Lettersspa
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85919-R/ES/RECONOCIMIENTO SUPRAMOLECULAR HELICOIDAL: COMPLEJOS HOSTGUEST RIGIDOS Y SISTEMAS MOLECULARES AUTO-ENSAMBLADOS
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-84354-P/CONTROL DE LA AFINIDAD, DINAMICA Y ESTRUCTURA DE SISTEMAS SUPRAMOLECULARES AUTOAGREGADOS
dc.rights© 2019 American Chemical Society
dc.titleDouble protonation of a cis-Bipyridoallenophane detected via Chiral-Sensing Switch: the role of Ion Pairseng
dc.typearticlespa
dc.rights.accessRightsopenAccessspa
dc.identifier.doi10.1021/acs.orglett.9b02024
dc.identifier.editorhttps://doi.org/10.1021/acs.orglett.9b02024spa
dc.publisher.departamentoQuímica orgánicaspa
dc.publisher.grupoinvestigacionSíntese, Estructura e Simulación (S3)spa
dc.subject.unesco2306.16 Esteroquímica y Análisis Conformacionalspa
dc.date.updated2024-01-22T10:21:41Z
dc.computerCitationpub_title=Organic Letters|volume=21|journal_number=15|start_pag=5898|end_pag=5902spa
dc.referencesThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letter, copyright 2019 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: https://doi.org/10.1021/acs.orglett.9b02024


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