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Unusual Scaffold Rearrangement in Polyaromatic Hydrocarbons Driven by Concerted Action of Single Gold Atoms on a Gold Surface

Jesús I. Mendieta‐Moreno, Benjamín Mallada, Bruno de la Torre, Timothée Cadart, Martin Kotora, Pavel Jelı́nek

2022Angewandte Chemie International Edition31 citationsDOI

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.

Topics & Concepts

MoleculeCovalent bondChemistryCatalysisCleavage (geology)Conjugated systemBond cleavageAtom (system on chip)PhotochemistryHydrocarbonNanotechnologyChemical physicsMaterials scienceOrganic chemistryPolymerComputer scienceEmbedded systemComposite materialFracture (geology)Surface Chemistry and CatalysisMolecular Junctions and NanostructuresAsymmetric Hydrogenation and Catalysis
Unusual Scaffold Rearrangement in Polyaromatic Hydrocarbons Driven by Concerted Action of Single Gold Atoms on a Gold Surface | Litcius