Highly selective on-surface ring-opening of aromatic azulene moiety

0584954 - FZÚ 2025 RIV US eng J - Journal Article
Wang, L. L. - Peng, X.N. - Su, J. - Wang, J.T. - Gallardo Caparrós, Aurelio Jesús - Yang, H. - Chen, Qifan - Lyu, P. - Jelínek, Pavel - Liu, J.Z. - Wong, M.W. - Lu, J.
Highly selective on-surface ring-opening of aromatic azulene moiety.
Journal of the American Chemical Society. Roč. 146, č. 2 (2024), s. 1563-1571. ISSN 0002-7863. E-ISSN 1520-5126
R&D Projects: GA ČR(CZ) GX20-13692X
Research Infrastructure: CzechNanoLab II - 90251
Institutional support: RVO:68378271
Keywords : on-surface reaction * mechanisms * benzene
OECD category: Physical chemistry
Impact factor: 15, year: 2022

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.
Permanent Link: https://hdl.handle.net/11104/0352742