Carbon‐Carbon Coupling on Inert Surfaces by Deposition of En Route Generated Aryl Radicals
| Autor: | Gianluca Galeotti, Markus Lackinger, Massimo Fritton |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Inert
Materials science 010405 organic chemistry Radical Aryl On‐Surface Synthesis scanning probe microscopy Substrate (chemistry) surface chemistry General Chemistry 010402 general chemistry Photochemistry 01 natural sciences Catalysis 0104 chemical sciences Molecular wire chemistry.chemical_compound radical coupling chemistry Terphenyl Deposition (phase transition) on-surface synthesis Reactivity (chemistry) Research Articles Research Article |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202010833 |
| Popis: | To facilitate C−C coupling in on‐surface synthesis on inert surfaces, we devised a radical deposition source (RDS) for the direct deposition of aryl radicals onto arbitrary substrates. Its core piece is a heated reactive drift tube through which halogenated precursors are deposited and en route converted into radicals. For the proof of concept we study 4,4′′‐diiodo‐p‐terphenyl (DITP) precursors on iodine‐passivated metal surfaces. Deposition with the RDS at room temperature results in highly regular structures comprised of mostly monomeric (terphenyl) or dimeric (sexiphenyl) biradicals. Mild heating activates progressive C−C coupling into more extended molecular wires. These structures are distinctly different from the self‐assemblies observed upon conventional deposition of intact DITP. Direct deposition of radicals renders substrate reactivity unnecessary, thereby paving the road for synthesis on application‐relevant inert surfaces. Terphenyl biradicals are generated from iodinated precursors en route by deposition through the reactive drift tube of a newly devised radical deposition source. Upon deposition onto iodine‐passivated metal surfaces, the terphenyl radicals self‐assemble into ordered structures but remain active for C−C coupling into dimers and extended oligomers. |
| Databáze: | OpenAIRE |
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