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Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene
Alberto Abengózar1, Patricia García-García1, David Sucunza1
1Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá , 28871 Alcalá de Henares, Madrid, Spain.
Abstract:
4a-Aza-10a-boraphenanthrene has been synthesized in only four steps from commercially available materials with a remarkable overall yield of 62%. In contrast to other BN-isosteres of phenathrene, this isomer is weakly fluorescent, which has been explained by means of computational studies that found a low energy conical intersection for the nonradiative deactivation of the excited state. Moreover, a completely regioselective functionalization of 4a-aza-10a-boraphenanthrene at C-1 by reaction with activated electrophiles has been achieved.
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