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

Angew Chem Int Ed Engl. 2018 Aug 13;57(33):10635-10639. doi: 10.1002/anie.201805852. Epub 2018 Jul 3.

Abstract

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 D3 -symmetrical propeller-shaped structure with three equivalent nanographene foils. The structure of the second diastereoisomer is C2 -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 D3 -symmetrical derivative has been achieved and CD measurements revealed extremely strong Cotton effects.

Keywords: azaarene; chirality; nanographene; polycyclic aromatic compounds; twisted molecules.