Facile synthesis of a pyrrole-fused dibenzo[a,e]pentalene and its application as a new extended, ladder-type fused aromatic system.

A novel ladder-type pyrrole-fused dibenzo[a,e]pentalene, in which two benzo[a,e]pentalene units are held coplanar by a nitrogen bridge, is synthesized via double intermolecular Pd-catalyzed cascade crossover annulations. The introduction of a nitrogen bridge not only has a substantial influence on the optoelectronic properties but also improves the processability and stability.