Competing Annulene and Radialene Structures in a Single Anti-Aromatic Molecule Studied by High-Resolution Atomic Force Microscopy
Research output: Contribution to journal › Article › Scientific › peer-review
Researchers
Research units
- National Institute for Materials Science Tsukuba
- Japan Science and Technology Agency
- University of Tokyo
- University of Basel
- Netherlands Organisation for Scientific Research
- Nanolayers Research Computing Ltd
- Kanazawa University
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.
Details
| Original language | English |
|---|---|
| Pages (from-to) | 8122-8130 |
| Number of pages | 9 |
| Journal | ACS Nano |
| Volume | 11 |
| Issue number | 8 |
| Publication status | Published - 22 Aug 2017 |
| MoE publication type | A1 Journal article-refereed |
- anti-aromaticity, atomic force microscopy, chemical structure, density functional theory calculation, on-surface chemical reaction, radialene
Research areas
ID: 15103045
