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A New Member of the BN-phenanthrene Family: Understanding the Role of the B-N Bond Position

dc.contributor.authorAbengózar Muñoz, Alberto 
dc.contributor.authorGarcía García, Patricia
dc.contributor.authorSucunza Sáenz, David 
dc.contributor.authorSampedro, Diego
dc.contributor.authorPérez Redondo, Adrián 
dc.contributor.authorVaquero López, Juan J.
dc.date.accessioned2020-07-15T10:26:09Z
dc.date.available2020-07-15T10:26:09Z
dc.date.issued2019-06-07
dc.identifier.bibliographicCitationJournal of Organic Chemistry, 2019, v. 84, n. 11, p. 7113-7122en
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10017/43794en
dc.description.abstract3,4-Dihydro-4-aza-3-boraphenanthrene, which shows the highest fluorescence quantum yield of all non-substituted BN-phenanthrenes reported to date (ϕF = 0.61), has been synthesized in only three steps (76% overall yield) from easily accessible 1-bromo-2-vinylnaphthalene, along with several substituted derivatives. The reactivity of these previously unknown BN-aromatic compounds towards organolithium compounds and bromine has been studied. This latter reaction affords bromo-substituted compounds that are suitable for further functionalization via Suzuki and Sonogashira couplings, with complete regioselectivity. The optical properties and excited state deactivation mechanisms of selected compounds were studied using computational methods.en
dc.format.mimetypeapplication/pdfen
dc.language.isoengen
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)en
dc.rights© 2019 American Chemical Societyen
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subjectBN-areneen
dc.subject3,4-dihydro-4-aza-3-boraphenanthreneen
dc.subjectfluorescenceen
dc.subjectbrominationen
dc.subjectorganolithium compounden
dc.titleA New Member of the BN-phenanthrene Family: Understanding the Role of the B-N Bond Positionen
dc.typeinfo:eu-repo/semantics/articleen
dc.subject.ecienciaQuímicaes_ES
dc.subject.ecienciaChemistryen
dc.contributor.affiliationUniversidad de Alcalá. Departamento de Química Orgánica y Química Inorgánicaes_ES
dc.date.updated2020-07-15T10:25:37Z
dc.type.versioninfo:eu-repo/semantics/publishedVersionen
dc.identifier.doi10.1021/acs.joc.9b00800en
dc.relation.projectIDCTQ2017-85263-R and CTQ2017-87372-P (Ministerio de Ciencia, Innovación y Universidades, AEI, FEDER); RETIC REDINREN RD16/0009/0015 (Instituto de Salud Carlos III, FEDER); CCG2018/EXP-005 and CCG2018/EXP-008 (University of Alcalá)es_ES
dc.rights.accessRightsinfo:eu-repo/semantics/openAccessen
dc.identifier.uxxiAR/0000031577en
dc.identifier.publicationtitleJournal of Organic Chemistryen
dc.identifier.publicationvolume84en
dc.identifier.publicationlastpage7122
dc.identifier.publicationissue11
dc.identifier.publicationfirstpage7113


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