Valencia et al. J Org Chem. 2021;:. 1,10a-Dihydro-1-aza-10a-boraphenanthrene and 6a,7-Dihydro-7-aza-6a-boratetraphene: Two New Fluorescent BN-PAHs.

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

1. Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Universidad de Alcalá, IRYCIS, Campus Científico-Tecnológico, 28805 Alcalá de Henares, Spain.  2. Departamento de Química Analítica, Química Física e Ingeniería Química, Instituto de Investigación Química "Andrés M. del Río" (IQAR), Universidad de Alcalá, Campus Científico-Tecnológico, 28805 Alcalá de Henares, Spain.

Abstract

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 ϕ(F) = 0.80).

graphical abstract