Synthesis of Boron-Doped Polycyclic Aromatic Hydrocarbons by Tandem Intramolecular Electrophilic Arene Borylation

Tandem intramolecular electrophilic
arene borylation was developed
to facilitate access to B-doped polycyclic aromatic hydrocarbons (PAHs).
DFT calculations revealed that electrophilic arene borylation occurred
via a four-membered ring transition state, in which C–B and
H–Br bonds formed in a concerted manner. An organic light-emitting
diode employing the B-doped PAH as an emitter and a B-doped PAH-based
field-effect transistor were successfully fabricated, demonstrating
the potential of B-doped PAHs in materials science.