Competing Annulene and Radialene Structures in a Single Anti-Aromatic Molecule Studied by High-Resolution Atomic Force Microscopy
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A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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en
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9
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ACS Nano, Volume 11, issue 8, pp. 8122-8130
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.Description
| openaire: EC/FP7/610446/EU//PAMS
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Kawai, S, Takahashi, K, Ito, S, Pawlak, R, Meier, T, Spijker, P, Canova, F F, Tracey, J, Nozaki, K, Foster, A S & Meyer, E 2017, 'Competing Annulene and Radialene Structures in a Single Anti-Aromatic Molecule Studied by High-Resolution Atomic Force Microscopy', ACS Nano, vol. 11, no. 8, pp. 8122-8130. https://doi.org/10.1021/acsnano.7b02973