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

Shigeki Kawai*, Keisuke Takahashi, Shingo Ito, Rémy Pawlak, Tobias Meier, Peter Spijker, Filippo Federici Canova, John Tracey, Kyoko Nozaki, Adam S. Foster, Ernst Meyer

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

29 Citations (Scopus)

Abstract

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
Volume11
Issue number8
DOIs
Publication statusPublished - 22 Aug 2017
MoE publication typeA1 Journal article-refereed

Keywords

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

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