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...
| Autores: | , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2019 |
| País: | España |
| Institución: | Universidad de Alcalá (UAH) |
| Repositorio: | e_Buah Biblioteca Digital Universidad de Alcalá |
| Idioma: | inglés |
| OAI Identifier: | oai:ebuah.uah.es:10017/43794 |
| Acceso en línea: | http://hdl.handle.net/10017/43794 https://dx.doi.org/10.1021/acs.joc.9b00800 |
| Access Level: | acceso abierto |
| Palabra clave: | BN-arene 3,4-dihydro-4-aza-3-boraphenanthrene fluorescence bromination organolithium compound Química Chemistry |
| Sumario: | 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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