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- Publisher Website: 10.1021/jacs.0c05668
- Scopus: eid_2-s2.0-85089607479
- PMID: 32657120
- WOS: WOS:000558793400041
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Article: On-Surface Synthesis of Non-Benzenoid Nanographenes by Oxidative Ring-Closure and Ring-Rearrangement Reactions
Title | On-Surface Synthesis of Non-Benzenoid Nanographenes by Oxidative Ring-Closure and Ring-Rearrangement Reactions |
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Authors | |
Issue Date | 2020 |
Publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html |
Citation | Journal of the American Chemical Society, 2020, v. 142 n. 31, p. 13565-13572 How to Cite? |
Abstract | Nanographenes (NGs) have gained increasing attention due to their immense potential as tailor-made organic materials for nanoelectronics and spintronics. They exhibit a rich spectrum of physicochemical properties that can be tuned by controlling the size or the edge structure or by introducing structural defects in the honeycomb lattice. Here, we report the design and on-surface synthesis of NGs containing several odd-membered polycycles induced by a thermal procedure on Au(111). Our scanning tunneling microscopy, noncontact atomic force microscopy, and scanning tunneling spectroscopy measurements, complemented by computational investigations, describe the formation of two nonbenzenoid NGs (2A,B) containing four embedded azulene units in the polycyclic framework, via on-surface oxidative ring-closure reactions. Interestingly, we observe surface-catalyzed skeletal ring rearrangement reactions in the NGs, which lead to the formation of additional heptagonal rings as well as pentalene and as-indacene units in 2A,B, respectively. 2A,B on Au(111) both exhibit narrow experimental frontier electronic gaps of 0.96 and 0.85 eV, respectively, and Fermi level pinning of their HOMOs together with considerable electron transfer to the substrate. Ab initio calculations estimate moderate open-shell biradical characters for the NGs in the gas phase. |
Persistent Identifier | http://hdl.handle.net/10722/286161 |
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 | Lohr, TG | - |
dc.contributor.author | Urgel, JI | - |
dc.contributor.author | Eimre, K | - |
dc.contributor.author | Liu, J | - |
dc.contributor.author | Giovannantonio, MD | - |
dc.contributor.author | Mishra, S | - |
dc.contributor.author | Berger, R | - |
dc.contributor.author | Ruffieux, P | - |
dc.contributor.author | Pignedoli, CA | - |
dc.contributor.author | Fasel, R | - |
dc.contributor.author | Feng, X | - |
dc.date.accessioned | 2020-08-31T06:59:59Z | - |
dc.date.available | 2020-08-31T06:59:59Z | - |
dc.date.issued | 2020 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2020, v. 142 n. 31, p. 13565-13572 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/286161 | - |
dc.description.abstract | Nanographenes (NGs) have gained increasing attention due to their immense potential as tailor-made organic materials for nanoelectronics and spintronics. They exhibit a rich spectrum of physicochemical properties that can be tuned by controlling the size or the edge structure or by introducing structural defects in the honeycomb lattice. Here, we report the design and on-surface synthesis of NGs containing several odd-membered polycycles induced by a thermal procedure on Au(111). Our scanning tunneling microscopy, noncontact atomic force microscopy, and scanning tunneling spectroscopy measurements, complemented by computational investigations, describe the formation of two nonbenzenoid NGs (2A,B) containing four embedded azulene units in the polycyclic framework, via on-surface oxidative ring-closure reactions. Interestingly, we observe surface-catalyzed skeletal ring rearrangement reactions in the NGs, which lead to the formation of additional heptagonal rings as well as pentalene and as-indacene units in 2A,B, respectively. 2A,B on Au(111) both exhibit narrow experimental frontier electronic gaps of 0.96 and 0.85 eV, respectively, and Fermi level pinning of their HOMOs together with considerable electron transfer to the substrate. Ab initio calculations estimate moderate open-shell biradical characters for the NGs in the gas phase. | - |
dc.language | eng | - |
dc.publisher | American Chemical Society. The Journal's web site is located at http://pubs.acs.org/journals/jacsat/index.html | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | On-Surface Synthesis of Non-Benzenoid Nanographenes by Oxidative Ring-Closure and Ring-Rearrangement Reactions | - |
dc.type | Article | - |
dc.identifier.email | Liu, J: juliu@hku.hk | - |
dc.identifier.authority | Liu, J=rp02584 | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jacs.0c05668 | - |
dc.identifier.pmid | 32657120 | - |
dc.identifier.scopus | eid_2-s2.0-85089607479 | - |
dc.identifier.hkuros | 313172 | - |
dc.identifier.volume | 142 | - |
dc.identifier.issue | 31 | - |
dc.identifier.spage | 13565 | - |
dc.identifier.epage | 13572 | - |
dc.identifier.isi | WOS:000558793400041 | - |
dc.publisher.place | United States | - |
dc.identifier.issnl | 0002-7863 | - |