How Boron Doping Shapes the Optoelectronic Properties of Canonical and Phenylene-Containing Oligoacenes: A Combined Experimental and Theoretical Investigation.

Optimized syntheses of 6,13-dimesityl-6,13-dihydro-6,13-diborapentacene ( DBP) and a related compound ( DBI) featuring two biphenylene-2,3-diyl units in place of naphthalene-2,3-diyl moieties are reported. Striking differences between the optoelectronic properties of DBP and DBI have been experimentally observed, and explained by quantum chemical calculations. DBP is a member of the oligoacene family, DBI is a linear [ N]phenylene derivative. The yellow DBP shows blue photoluminescence, the deep red DBI is nonfluorescent. Both compounds give rise to two reversible redox transitions at E [ABSTRACT FROM AUTHOR]