On-Surface Annulation Reaction Cascade for the Selective Synthesis of Diindenopyrene
Eisenhut F, Lehmann T, Viertel A, Skidin D, Kruger J, Nikipar S, Ryndyk DA, Joachim C, Hecht S, Moresco F, Cuniberti G (2017)
Publication Type: Journal article
Publication year: 2017
Journal
Book Volume: 11
Pages Range: 12419-12425
Journal Issue: 12
Abstract
We investigated the thermally induced on-surface cyclization of 4,10-bis(2′-bromo-4′-methylphenyl)-1,3-dimethylpyrene to form the previously unknown, nonalternant polyaromatic hydrocarbon diindeno[1,2,3-cd:1′,2′,3′-mn]pyrene on Au(111) using scanning tunneling microscopy and spectroscopy. The observed unimolecular reaction involves thermally induced debromination followed by selective ring closure to fuse the neighboring benzene moieties via a five-membered ring. The structure of the product has been verified experimentally as well as theoretically. Our results demonstrate that on-surface reactions give rise to unusual chemical reactivities and selectivities and provide access to nonalternant polyaromatic molecules.
Involved external institutions
Technische Universität Dresden
Germany (DE)
Humboldt-Universität zu Berlin
Germany (DE)
National Center for Scientific Research / Centre national de la recherche scientifique (CNRS)
France (FR)
Germany (DE)
Humboldt-Universität zu Berlin
Germany (DE)
National Center for Scientific Research / Centre national de la recherche scientifique (CNRS)
France (FR)
How to cite
APA:
Eisenhut, F., Lehmann, T., Viertel, A., Skidin, D., Kruger, J., Nikipar, S.,... Cuniberti, G. (2017). On-Surface Annulation Reaction Cascade for the Selective Synthesis of Diindenopyrene. ACS nano, 11(12), 12419-12425. https://doi.org/10.1021/acsnano.7b06459
MLA:
Eisenhut, Frank, et al. "On-Surface Annulation Reaction Cascade for the Selective Synthesis of Diindenopyrene." ACS nano 11.12 (2017): 12419-12425.
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