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

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 substitute...

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Bibliographic Details
Authors: Abengózar Muñoz, Alberto, García García, Patricia|||0000-0003-3671-5828, Sucunza Sáenz, David|||0000-0002-3307-4204, Sampedro Ruiz, Diego, Pérez Redondo, Adrián|||0000-0002-0086-8825, Vaquero López, Juan José|||0000-0002-3820-9673
Format: article
Publication Date:2019
Country:España
Institution:Universidad de Alcalá (UAH)
Repository:e_Buah Biblioteca Digital Universidad de Alcalá
Language:English
OAI Identifier:oai:ebuah.uah.es:10017/43794
Online Access:http://hdl.handle.net/10017/43794
https://dx.doi.org/10.1021/acs.joc.9b00800
Access Level:Open access
Keyword:BN-arene
3,4-dihydro-4-aza-3-boraphenanthrene
fluorescence
bromination
organolithium compound
Química
Chemistry
Description
Summary: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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