On-surface synthesis of a phenylene analogue of nonacene

Chem Commun (Camb). 2022 Mar 24;58(25):4063-4066. doi: 10.1039/d2cc00479h.

Abstract

Cyclobuta[1,2-b:3,4-b']ditetracene - an analogue of nonacene with a cyclobutadiene unit embedded in the central part has been synthesized by the combination of solution and on-surface chemistry. The atomic structure and electronic properties of the product on Au(111) have been determined by high resolution scanning tunnelling microscopy/spectroscopy corroborated by density functional theory calculations. Structural and magnetic parameters derived from theoretical calculations reveal that π conjugation is dominated by radialene-type contribution, with an admixture of cyclobutadiene-like antiaromaticity.