Synthesis of Nitrogen-Containing Rubicene and Tetrabenzopentacene Derivatives

Carbon-based materials, such as acenes, fullerenes, and graphene nanoribbons, are viewed as the potential successors to silicon in the next generation of electronics. Although a number of methodologies provide access to these materials' all-carbon variants, relatively fewer strategies readily furnish their nitrogen-doped analogues. Herein, we report the rational design, preparation, and characterization of nitrogen-containing rubicenes and tetrabenzopentacenes, which can be viewed either as acene derivatives or as molecular fragments of fullerenes and graphene nanoribbons. The reported findings may prove valuable for the development of electron transporting organic semiconductors and for the eventual construction of larger carbonaceous systems.