Synthesis, Characterization, and Properties of BN-Fluoranthenes

Boron/nitrogen-doped fluoranthenes,
a new class of BN-doped cyclopenta-fused
polycyclic aromatic hydrocarbons, were synthesized via pyrrolic-type
nitrogen directed C–H borylation. Regioselective bromination
of BN-fluoranthene (3a) gave mono- and dibrominated BN-fluoranthenes.
The halogenated BN-fluoranthene (3b) can undergo various
of further cross-coupling reactions to deliver a series of BN-fluoranthenes.
Moreover, incorporating BN unit in to fluoranthene resulted in a wider
HOMO–LUMO energy gaps. The aromaticities of the BN-fluoranthene
(3a) were quantified by experimental and computational
studies.