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.