Real-space imaging of a phenyl group migration reaction on metal surfaces

Zilin Ruan, Baijin Li, Jianchen Lu (), Lei Gao (), Shijie Sun, Yong Zhang and Jinming Cai ()
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Zilin Ruan: Kunming University of Science and Technology
Baijin Li: Kunming University of Science and Technology
Jianchen Lu: Kunming University of Science and Technology
Lei Gao: Kunming University of Science and Technology
Shijie Sun: Kunming University of Science and Technology
Yong Zhang: Kunming University of Science and Technology
Jinming Cai: Kunming University of Science and Technology

Nature Communications, 2023, vol. 14, issue 1, 1-6

Abstract: Abstract The explorations to extend present chemical synthetic methods are of great importance to simplify synthetic routes of chemical species. Additionally, understanding the chemical reaction mechanisms is critical to achieve controllable synthesis for applications. Here, we report the on-surface visualization and identification of a phenyl group migration reaction of 1,4-dimethyl-2,3,5,6-tetraphenyl benzene (DMTPB) precursor on Au(111), Cu(111) and Ag(110) substrates. With the combination of bond-resolved scanning tunneling microscopy (BR-STM), noncontact atomic force microscopy (nc-AFM) and density functional theory (DFT) calculations, the phenyl group migration reaction of DMTPB precursor is observed, forming various polycyclic aromatic hydrocarbons on the substrates. DFT calculations reveal that the multiple-step migrations are facilitated by the hydrogen radical attack, inducing cleavage of phenyl groups and subsequent rearomatization of the intermediates. This study provides insights into complex surface reaction mechanisms at the single molecule level, which may guide the design of chemical species.

Date: 2023
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DOI: 10.1038/s41467-023-36696-6

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