RT info:eu-repo/semantics/article T1 A New Member of the BN-phenanthrene Family: Understanding the Role of the B-N Bond Position A1 Abengózar Muñoz, Alberto A1 García García, Patricia A1 Sucunza Sáenz, David A1 Sampedro, Diego A1 Pérez Redondo, Adrián A1 Vaquero López, Juan J. K1 BN-arene K1 3,4-dihydro-4-aza-3-boraphenanthrene K1 fluorescence K1 bromination K1 organolithium compound K1 Química K1 Chemistry AB 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. SN 0022-3263 YR 2019 FD 2019-06-07 LK http://hdl.handle.net/10017/43794 UL http://hdl.handle.net/10017/43794 LA eng DS MINDS@UW RD 29-mar-2024