Synthesis, Functionalization, and Optical Properties of 1,2-Dihydro-1-aza-2-boraphenanthrene and Several Highly Fluorescent Derivatives

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/10017/43802
DOI: 10.1021/acs.orglett.9b00448
ISSN: 1523-7060
Date
2019-04-19
Affiliation
Universidad de Alcalá. Departamento de Química Orgánica y Química Inorgánica
Bibliographic citation
Organic Letters, 2019, v. 21, n. 8, p. 2550-2554
Keywords
BN-arene
1,2-dihydro-1-aza-2-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
Previously unknown 1,2-dihydro-1-aza-2-boraphenanthrene has been synthesized in only three steps from 2-bromo-1-vinylnaphthalene. The reactivity of this new BN-phenanthrene, and of several substituted derivatives, has been tested against bromine and organolithium compounds. Bromination proceeded with complete regioselectivity, affording bromo-substituted compounds suitable for further functionalization via cross coupling reactions. This new family of BN-phenanthrenes exhibits a substantial increase in the quantum yield (up to ϕF = 0.93) with respect to phenanthrene.
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