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In Situ Coupling of Single Molecules Driven by Gold‐Catalyzed Electrooxidation
Author(s) -
Zang Yaping,
Stone Ilana,
Inkpen Michael S.,
Ng Fay,
Lambert Tristan H.,
Nuckolls Colin,
Steigerwald Michael L.,
Roy Xavier,
Venkataraman Latha
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201906215
Subject(s) - azobenzene , scanning tunneling microscope , molecule , in situ , aniline , catalysis , break junction , oxidative coupling of methane , electrochemistry , chemistry , conductance , nanoscopic scale , nanotechnology , quantum tunnelling , coupling (piping) , molecular wire , combinatorial chemistry , materials science , electrode , organic chemistry , optoelectronics , mathematics , combinatorics , metallurgy
A single‐molecule method has been developed based on the scanning tunneling microscope (STM) to selectively couple a series of aniline derivatives and create azobenzenes. The Au‐catalyzed oxidative coupling is driven by the local electrochemical potential at the nanostructured Au STM tip. The products are detected in situ by measuring the conductance and molecular junction elongation and compared with analogous measurements of the expected azobenzene derivatives prepared ex situ. This single‐molecule approach is robust, and it can quickly and reproducibly create reactions for a variety of anilines. We further demonstrate the selective synthesis of geometric isomers and the assembly of complex molecular architectures by sequential coupling of complementary anilines, demonstrating unprecedented control over bond formation at the nanoscale.