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Azo bond formation on metal surfaces
Author(s) -
Meng Xiangzhi,
Klaasen Henning,
Viergutz Lena,
Schulze Lammers Bertram,
Witteler Melanie C.,
Mönig Harry,
Amirjalayer Saeed,
Liu Lacheng,
Neugebauer Johannes,
Gao HongYing,
Studer Armido,
Fuchs Harald
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011858
Subject(s) - x ray photoelectron spectroscopy , coupling reaction , chemistry , scanning tunneling microscope , nitro , redox , reaction mechanism , metal , photochemistry , polymer , polymer chemistry , inorganic chemistry , chemical engineering , materials science , organic chemistry , nanotechnology , catalysis , alkyl , engineering
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.