Research Abstract


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

2017年7月20日 Nature Communications 8 : 16089 doi: 10.1038/ncomms16089 (2017)


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

Corresponding Authors

塩足 亮隼
東京大学大学院 新領域創成科学研究科 物質系専攻

中江 隆博
京都大学 エネルギー理工学研究所

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.