A Twisted Nanographene Consisting of 96 Carbon Atoms

Herein we report synthesis, structure and properties of a new type of twisted nanographene, which contains an [8]circulene moiety in a polycyclic framework of 96 sp(2) carbon atoms. The key steps in this synthesis are the Diels-Alder reaction of a macrocyclic diyne and the subsequent Scholl reaction forming the [8]circulene moiety. Two incompletely cyclized products were isolated from the Scholl reaction, providing insight into the cyclization of the strained octagon. This nanographene is twisted along two directions with end-to-end twists of 142.4 degrees and 140.2 degrees as revealed by X-ray crystallography, and is flexible at room temperature as found from the computational and experimental studies.