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

AI Article Synopsis

  • Researchers have found a way to control the structural changes of organic molecules on metal surfaces, leading to unique chemical reactions.
  • They demonstrate this using high-resolution atomic force microscopy to rearrange a specific polycyclic aromatic hydrocarbon (PAH) on a copper surface.
  • This method not only produces a new type of molecule never seen before but also offers a pathway for creating advanced nanocarbon materials that traditional methods can't achieve.

Article 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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5524995PMC
http://dx.doi.org/10.1038/ncomms16089DOI Listing

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