journal article·2017-08-22

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

ACS Nano· Volume 11· Issue 8
Publisher page

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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Research context

OpenAlex topics: Surface Chemistry and Catalysis · Graphene research and applications · Molecular Junctions and Nanostructures

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

International Center for Materials Nanoarchitectonics, National Institute for Materials Science, 1-1, Namiki, Tsukuba, Ibaraki 305-0044, Japan

PESTO, Japan Science and Technology Agency, 4-1-8, Honcho, Kawaguchi, Saitama 332-0012, Japan

Department of Chemistry and Biotechnology, Graduate School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan

Department of Physics, University of Basel, Klingelbergstrasse 82, CH-4056 Basel, Switzerland

COMP, Department of Applied Physics, Aalto University, P.O. Box 11100, FI-00076 Aalto, Finland

Netherlands Organisation for Scientific Research, Domain Science, P.O. Box 3021, 3527 JP, Utrecht, The Netherlands

Nanolayers Research Computing LTD, 15 Southgrove Road, Sheffield, United Kingdom, S10 2NP

Division of Electrical Engineering and Computer Science, Kanazawa University, Kanazawa 920-1192, Japan

Funding

FP7 Information and Communication Technologies · Schweizerischer Nationalfonds zur F?rderung der Wissenschaftlichen Forschung · Precursory Research for Embryonic Science and Technology · European Cooperation in Science and Technology · Japan Society for the Promotion of Science · Japan Science and Technology Agency · Suomen Akatemia

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