Unusual Scaffold Rearrangement in Polyaromatic Hydrocarbons Driven by Concerted Action of Single Gold Atoms on a Gold Surface. (15th November 2022)

• Record Type: Journal Article
• Authors: Mendieta‐Moreno, Jesús I.; Mallada, Benjamin; de la Torre, Bruno; Cadart, Timothée; Kotora, Martin; Jelínek, Pavel
• Is Part Of: Angewandte Chemie. Volume 134:Number 50(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-11-15
• Subjects: (PAH) Polyaromatic Hydrocarbon -- (SPM) Scanning Probe Microscopy -- on-Surface Synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202208010
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Chemical transformation of polyaromatic hydrocarbon (PAH) molecules following different reaction strategies has always been the focus of organic synthesis. In this work, we report the synthesis of a PAH molecule, formation of which consists of an unusual C−C bond cleavage accompanied by a complex π‐conjugated molecular scaffold rearrangement. We demonstrate that the complex chemical transformation is steered by concerted motion of individual Au 0 gold atoms on a supporting Au(111) surface. This observation underpins the importance of single‐atom catalysis mediated by adatoms in on‐surface synthesis as well as catalytic activity of single Au 0 atoms facilitating cleavage of covalent carbon bonds. Abstract : The on‐surface synthesis of a polyaromatic hydrocarbon molecule is described. Mechanistically, the synthesis involves an unusual C−C bond cleavage catalyzed by Au adatoms with a molecular scaffold rearrangement. This rearrangement in the π‐conjugated molecular scaffold is possible because of the concerted action of two Au adatoms that catalyze the reaction on the gold surface.