Synthesis of a Helical Bilayer Nanographene

Abstract

A rigid, inherently chiral bilayer nanographene has been synthesized as both the racemate and enantioenriched M isomer (with 93 % ee) in three steps from established helicenes. This folded nanographene is composed of two hexa-peri-hexabenzocoronene layers fused to a [10]helicene, with an interlayer distance of 3.6 Å as determined by X-ray crystallography. The rigidity of the helicene linker forces the layers to adopt a nearly aligned AA-stacked conformation, rarely observed in few-layer graphene. By combining the advantages of nanographenes and helicenes, we have constructed a bilayer system of 30 fused benzene rings that is also chiral, rigid, and remains soluble in common organic solvents. We present this as a molecular model system of bilayer graphene, with properties of interest in a variety of potential applications.

Keywords: arenes; bilayer graphene; chirality; helicenes; nanographene.