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Title: Strain-induced skeletal rearrangement of a polycyclic aromatic hydrocarbon on a copper surface
Authors: Shiotari, Akitoshi
Nakae, Takahiro
Iwata, Kota
Mori, Shigeki
Okujima, Tetsuo
Uno, Hidemitsu
Sakaguchi, Hiroshi  kyouindb  KAKEN_id
Sugimoto, Yoshiaki
Author's alias: 塩足, 亮隼
中江, 隆博
岩田, 孝太
森, 重樹
奥島, 鉄雄
宇野, 英満
坂口, 浩司
杉本, 宜昭
Keywords: Atomic force microscopy
Synthetic chemistry methodology
Scanning probe microscopy
Surfaces, interfaces and thin films
Issue Date: 20-Jul-2017
Publisher: Springer Nature
Journal title: Nature Communications
Volume: 8
Thesis number: 16089
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.
Description: 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.
Rights: © The Author(s) 2017. This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit
DOI(Published Version): 10.1038/ncomms16089
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