Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 3, Pages 1458-1464Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202011858
Keywords
Azo formation; conjugated polymers; cross-coupling; STM; surface chemistry
Categories
Funding
- Deutsche Forschungsgemeinschaft [SFB858, TRR61, FU299/19, GA2430/1-1, MO2345/4-1, AM460/2-1]
- NSFC [21972104]
- 1000-Youth Talents Plan
- Alexander vonHumboldt foundation
- Projekt DEAL
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The efficient formation of azo compounds via redox cross-coupling of nitroarenes and arylamines has been achieved through on-surface chemistry. The use of well-designed precursors containing both an amino and a nitro functionality results in highly efficient nitro-amino cross-coupling on the surface. The metal surface was found to have a significant effect on the reaction efficiency, with the reaction proceeding from partially oxidized/reduced precursors in dimerization reactions.
The formation of azo compounds via redox cross-coupling of nitroarenes and arylamines, challenging in solution phase chemistry, is achieved by on-surface chemistry. Reaction products are analyzed with a cryogenic scanning tunneling microscope (STM) and X-ray photoelectron spectroscopy (XPS). By using well-designed precursors containing both an amino and a nitro functionality, azo polymers are prepared on surface via highly efficient nitro-amino cross-coupling. Experiments conducted on other substrates and surface orientations reveal that the metal surface has a significant effect on the reaction efficiency. The reaction was further found to proceed from partially oxidized/reduced precursors in dimerization reactions, shedding light on the mechanism that was studied by DFT calculations.
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