
ALT Abstract We use the selective incorporation of nitrogen into the sp²-carbon-based polycyclic scaffolds to efficiently modulate their optoelectronic and materials properties. In the resulting systems, the nitrogen readily adopts a planar sp²-hybridized geometry to provide for efficient electronic communication of its lone pair with the surrounding π-system. Moreover, the nitrogen can be reversibly oxidized to the corresponding radical cation with superior stability due to efficient delocalization of spin and charge throughout the π-conjugated framework. This approach yields a wide variety of nitrogen-doped polycyclic scaffolds with exciting properties that are of interest both as valuable objects for fundamental studies and as functional materials for diverse applications.















