Competing Annulene and Radialene Structures in a Single Anti-Aromatic Molecule Studied by High-Resolution Atomic Force Microscopy

Research output: Contribution to journalArticleScientificpeer-review


Research units

  • National Institute for Materials Science Tsukuba
  • Japan Science and Technology Agency
  • University of Tokyo
  • University of Basel
  • Netherlands Organisation for Scientific Research
  • Nanolayers Research Computing Ltd
  • Kanazawa University


According to Hückel theory, an anti-aromatic molecule possessing (4n)π-electrons becomes unstable. Although the stabilization has been demonstrated by radialene-type structures - fusing aromatic rings to anti-aromatic rings - in solution, such molecules have never been studied at a single molecular level. Here, we synthesize a cyclobutadiene derivative, dibenzo[b,h]biphenylene, by an on-surface intramolecular reaction. With a combination of high-resolution atomic force microscopy and density functional theory calculations, we found that a radialene structure significantly reduces the anti-aromaticity of the cyclobutadiene core, extracting π-electrons, while the small four-membered cyclic structure keeps a high density of the total charge.


Original languageEnglish
Pages (from-to)8122-8130
Number of pages9
JournalACS Nano
Issue number8
Publication statusPublished - 22 Aug 2017
MoE publication typeA1 Journal article-refereed

    Research areas

  • anti-aromaticity, atomic force microscopy, chemical structure, density functional theory calculation, on-surface chemical reaction, radialene

ID: 15103045