Strain-induced skeletal rearrangement of a polycyclic aromatic hydrocarbon on a copper surface

Akitoshi Shiotari (), Takahiro Nakae (), Kota Iwata, Shigeki Mori, Tetsuo Okujima, Hidemitsu Uno, Hiroshi Sakaguchi and Yoshiaki Sugimoto
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Akitoshi Shiotari: The University of Tokyo
Takahiro Nakae: Institute of Advanced Energy, Kyoto University
Kota Iwata: Graduate School of Engineering, Osaka University
Shigeki Mori: Advanced Research Support Center, Ehime University
Tetsuo Okujima: Graduate School of Science and Engineering, Ehime University
Hidemitsu Uno: Graduate School of Science and Engineering, Ehime University
Hiroshi Sakaguchi: Institute of Advanced Energy, Kyoto University
Yoshiaki Sugimoto: The University of Tokyo

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: Abstract Controlling the structural deformation of organic molecules can drive unique reactions that cannot be induced only by thermal, optical or electrochemical procedures. However, in conventional organic synthesis, including mechanochemical procedures, it is difficult to control skeletal rearrangement in polycyclic aromatic hydrocarbons (PAHs). Here, we demonstrate a reaction scheme for the skeletal rearrangement of PAHs on a metal surface using high-resolution noncontact atomic force microscopy. By a combination of organic synthesis and on-surface cyclodehydrogenation, we produce a well-designed PAH—diazuleno[1,2,3-cd:1′,2′,3′-fg]pyrene—adsorbed flatly onto Cu(001), in which two azuleno moieties are highly strained by their mutual proximity. This local strain drives the rearrangement of one of the azuleno moieties into a fulvaleno moiety, which has never been reported so far. Our proposed thermally driven, strain-induced synthesis on surfaces will pave the way for the production of a new class of nanocarbon materials that conventional synthetic techniques cannot attain.

Date: 2017
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DOI: 10.1038/ncomms16089

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