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

Shiotari, Akitoshi  ,  Nakae, Takahiro  ,  Iwata, Kota  ,  Mori, Shigeki  ,  Okujima, Tetsuo  ,  Uno, Hidemitsu  ,  Sakaguchi, Hiroshi  ,  Sugimoto, Yoshiaki

82017-07-20 , Springer Nature
金属表面で分子を曲げて骨格を変える新・有機合成法を開発 --原子間力顕微鏡を用いて炭素骨格変換の可視化に成功--. 京都大学プレスリリース. 2017-07-24.
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.

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