Twisted N-Doped Nano-Graphenes: Synthesis, Characterization, and Resolution

Two diastereoisomeric N-doped nanographene derivatives have been efficiently prepared in two synthetic steps starting from an ethynylated hexaazatriphenylene building block. The first derivative adopts a D-3-symmetrical propeller-shaped structure with three equivalent nanographene foils. The structure of the second diastereoisomer is C-2-symmetrical and differs from the first one by the way two peripheral nanographene foils overlap. Owing to their intertwined structures, the two N-doped nanographenes are soluble in organic solvents and could be characterized by a combination of several analytical tools. Resolution of the D-3-symmetrical derivative has been achieved and CD measurements revealed extremely strong Cotton effects.