A Twisted Nanographene Consisting of 96 Carbon Atoms. Issue 31 (16th May 2017)

• Record Type: Journal Article
• Authors: Cheung, Kwan Yin; Chan, Chi Kit; Liu, Zhifeng; Miao, Qian
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 31(2017)
• Page Start: 9003
• Page End: 9007
• Publication Date: 2017-05-16
• Subjects: arenes -- aromaticity -- polycycles -- stereochemistry -- strained molecules; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201703754
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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° and 140.2° as revealed by X‐ray crystallography, and is flexible at room temperature as found from the computational and experimental studies. Abstract : A new type of twisted nanographene containing an [8]circulene moiety in a polycyclic framework of 96 sp 2 carbon atoms was synthesized from a macrocyclic diyne (see picture). Its structure was studied with X‐ray crystallography and DFT calculations.