Azaarenes: 13 Rings in a Row by Cyclopentannulation

Angew Chem Int Ed Engl. 2023 Jan 26;62(5):e202214031. doi: 10.1002/anie.202214031. Epub 2022 Dec 22.

Abstract

Cyclopentannulation was explored as a strategy to access large, stable azaarenes. Buchwald-Hartwig coupling of previously reported di- and tetrabrominated cyclopentannulated N,N'-dihydrotetraazapentacenes furnished stable azaarenes with up to 13 six-membered rings in a row and a length of 3.1 nm. Their optoelectronic and semi-conducting properties as well as their aromaticity were investigated.

Keywords: Aromaticity; Azaacenes; Azaarenes; Cyclopentannulation; Molecular Nanocarbons.