ACS Nano
ACS Nano
4 years ago

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

Competing Annulene and Radialene Structures in a Single Anti-Aromatic Molecule Studied by High-Resolution Atomic Force Microscopy
John Tracey, Shigeki Kawai, Peter Spijker, Shingo Ito, Adam S. Foster, Tobias Meier, Keisuke Takahashi, Filippo Federici Canova, Ernst Meyer, Kyoko Nozaki, Rémy Pawlak
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.

Publisher URL: http://dx.doi.org/10.1021/acsnano.7b02973

DOI: 10.1021/acsnano.7b02973

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