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

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Volume Title

A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

Date

2017-08-22

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Language

en

Pages

9
8122-8130

Series

ACS NANO, Volume 11, issue 8

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.

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| openaire: EC/FP7/610446/EU//PAMS

Keywords

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

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Citation

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