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

Authors
Abengózar Muñoz, AlbertoUniversity of Alcalá Author; García García, PatriciaUniversity of Alcalá Author; Sucunza Sáenz, DavidUniversity of Alcalá Author; Sampedro, Diego; Pérez Redondo, AdriánUniversity of Alcalá Author; [et al.]
Identifiers
Permanent link (URI): http://hdl.handle.net/10017/43794
DOI: 10.1021/acs.joc.9b00800
ISSN: 0022-3263
Date
2019-06-07
Affiliation
Universidad de Alcalá. Departamento de Química Orgánica y Química Inorgánica
Bibliographic citation
Journal of Organic Chemistry, 2019, v. 84, n. 11, p. 7113-7122
Keywords
BN-arene
3,4-dihydro-4-aza-3-boraphenanthrene
fluorescence
bromination
organolithium compound
Project
CTQ2017-85263-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)
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
© 2019 American Chemical Society
Access rights
info:eu-repo/semantics/openAccess
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Abstract
3,4-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.
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