Strain-induced Skeletal Rearrangement of a Polycyclic Aromatic Hydrocarbon on a Copper Surface

Overview

Journal Nat Commun

Specialty Biology

Date 2017 Jul 21

PMID 28726802

Citations 9

Authors

Akitoshi Shiotari

Takahiro Nakae

Kota Iwata

Shigeki Mori

Tetsuo Okujima

Hidemitsu Uno

Hiroshi Sakaguchi

Yoshiaki Sugimoto

Affiliations

Soon will be listed here.

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.

Citing Articles

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