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On-Surface Hydrogen-Induced Covalent Coupling of Polycyclic Aromatic Hydrocarbons via a Superhydrogenated Intermediate

AuthorsSánchez-Sánchez, Carlos ; Martínez, José I. ; Ruiz del Árbol, Nerea ; Ruffieux, Pascal; Fasel, Roman; López, María Francisca ; Andrés, Pedro L. de ; Martín-Gago, José A.
Polycyclic aromatic hydrocarbons
Covalent coupling
Atomic hydrogen
On-surface chemistry
Issue Date9-Jan-2019
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 141(8): 3550-3557 (2019)
AbstractThe activation, hydrogenation, and covalent coupling of polycyclic aromatic hydrocarbons (PAHs) are processes of great importance in fields like chemistry, energy, biology, or health, among others. So far, they are based on the use of catalysts which drive and increase the efficiency of the thermally- or light-induced reaction. Here, we report on the catalyst-free covalent coupling of nonfunctionalized PAHs adsorbed on a relatively inert surface in the presence of atomic hydrogen. The underlying mechanism has been characterized by high-resolution scanning tunnelling microscopy and rationalized by density functional theory calculations. It is based on the formation of intermediate radical-like species upon hydrogen-induced molecular superhydrogenation which favors the covalent binding of PAHs in a thermally activated process, resulting in large coupled molecular nanostructures. The mechanism proposed in this work opens a door toward the direct formation of covalent, PAH-based, bottom-up synthesized nanoarchitectures on technologically relevant inert surfaces.
Publisher version (URL)https://doi.org/10.1021/jacs.8b12239
Appears in Collections:(ICMM) Artículos
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