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1,10a-Dihydro-1-aza-10a-boraphenanthrene and 6a,7-Dihydro-7-aza-6a-boratetraphene: Two New Fluorescent BN-PAHs

Isabel Valencia, Patricia García-García, David Sucunza*, Francisco Mendicuti, Juan J. Vaquero*

J. Org. Chem. 2021, 86, 23, 16259–16267
DOI: 10.1021/acs.joc.1c01095

Previously unknown 1,10a-dihydro-1-aza-10a-boraphenanthrene and 6a,7-dihydro-7-aza-6a-boratetraphene have been efficiently synthesized. Bromination of these BN-PAHs proceeds with complete regioselectivity, resulting in the formation of different substituted derivatives via cross-coupling reactions. These compounds exhibit rather high fluorescence quantum yields (up to ϕF = 0.80).