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- Publisher Website: 10.1021/jacs.3c11652
- Scopus: eid_2-s2.0-85181566151
- WOS: WOS:001144606800001
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Article: Highly Selective On-Surface Ring-Opening of Aromatic Azulene Moiety
Title | Highly Selective On-Surface Ring-Opening of Aromatic Azulene Moiety |
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Authors | |
Issue Date | 23-Dec-2023 |
Publisher | American Chemical Society |
Citation | Journal of the American Chemical Society, 2023, v. 146, n. 2, p. 1563-1571 How to Cite? |
Abstract | Controllable ring-opening of polycyclic aromatic hydrocarbons plays a crucial role in various chemical and biological processes. However, breaking down aromatic covalent C–C bonds is exceptionally challenging due to their high stability and strong aromaticity. This study presents a seminal report on the precise and highly selective on-surface ring-opening of the seven-membered ring within the aromatic azulene moieties under mild conditions. The chemical structures of the resulting products were identified using bond-resolved scanning probe microscopy. Furthermore, through density functional theory calculations, we uncovered the mechanism behind the ring-opening process and elucidated its chemical driving force. The key to achieving this ring-opening process lies in manipulating the local aromaticity of the aromatic azulene moiety through strain-induced internal ring rearrangement and cyclodehydrogenation. By precisely controlling these factors, we successfully triggered the desired ring-opening reaction. Our findings not only provide valuable insights into the ring-opening process of polycyclic aromatic hydrocarbons but also open up new possibilities for the manipulation and reconstruction of these important chemical structures. |
Persistent Identifier | http://hdl.handle.net/10722/339565 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Wang, Lulu | - |
dc.contributor.author | Peng, Xinnan | - |
dc.contributor.author | Su, Jie | - |
dc.contributor.author | Wang, Junting | - |
dc.contributor.author | Gallardo, Aurelio | - |
dc.contributor.author | Yang, Hui | - |
dc.contributor.author | Chen, Qifan | - |
dc.contributor.author | Lyu, Pin | - |
dc.contributor.author | Jelínek, Pavel | - |
dc.contributor.author | Liu, Junzhi | - |
dc.contributor.author | Wong, Ming Wah | - |
dc.contributor.author | Lu, Jiong | - |
dc.date.accessioned | 2024-03-11T10:37:41Z | - |
dc.date.available | 2024-03-11T10:37:41Z | - |
dc.date.issued | 2023-12-23 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2023, v. 146, n. 2, p. 1563-1571 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/339565 | - |
dc.description.abstract | <p>Controllable ring-opening of polycyclic aromatic hydrocarbons plays a crucial role in various chemical and biological processes. However, breaking down aromatic covalent C–C bonds is exceptionally challenging due to their high stability and strong aromaticity. This study presents a seminal report on the precise and highly selective on-surface ring-opening of the seven-membered ring within the aromatic azulene moieties under mild conditions. The chemical structures of the resulting products were identified using bond-resolved scanning probe microscopy. Furthermore, through density functional theory calculations, we uncovered the mechanism behind the ring-opening process and elucidated its chemical driving force. The key to achieving this ring-opening process lies in manipulating the local aromaticity of the aromatic azulene moiety through strain-induced internal ring rearrangement and cyclodehydrogenation. By precisely controlling these factors, we successfully triggered the desired ring-opening reaction. Our findings not only provide valuable insights into the ring-opening process of polycyclic aromatic hydrocarbons but also open up new possibilities for the manipulation and reconstruction of these important chemical structures.<br></p> | - |
dc.language | eng | - |
dc.publisher | American Chemical Society | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Highly Selective On-Surface Ring-Opening of Aromatic Azulene Moiety | - |
dc.type | Article | - |
dc.identifier.doi | 10.1021/jacs.3c11652 | - |
dc.identifier.scopus | eid_2-s2.0-85181566151 | - |
dc.identifier.volume | 146 | - |
dc.identifier.issue | 2 | - |
dc.identifier.spage | 1563 | - |
dc.identifier.epage | 1571 | - |
dc.identifier.eissn | 1520-5126 | - |
dc.identifier.isi | WOS:001144606800001 | - |
dc.identifier.issnl | 0002-7863 | - |