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Benzo-Fused Periacenes or Double Helicenes? Different Cyclodehydrogenation Pathways on Surface and in Solution
https://oist.repo.nii.ac.jp/records/1099
https://oist.repo.nii.ac.jp/records/1099ed68fdd6-154c-411a-a45a-cc8f853dbe62
名前 / ファイル | ライセンス | アクション |
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jacs.9b01267 (4.8 MB)
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Creative Commons Attribution 4.0 International (https://creativecommons.org/licenses/by/4.0/)
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Item type | 学術雑誌論文 / Journal Article(1) | |||||
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公開日 | 2019-09-11 | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | Benzo-Fused Periacenes or Double Helicenes? Different Cyclodehydrogenation Pathways on Surface and in Solution | |||||
言語 | ||||||
言語 | eng | |||||
資源タイプ | ||||||
資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
資源タイプ | journal article | |||||
著者(英) |
Zhong, Qigang
× Zhong, Qigang× Hu, Yunbin× Niu, Kaifeng× Zhang, Haiming× Yang, Biao× Ebeling, Daniel× Tschakert, Jalmar× Cheng, Tao× Schirmeisen, André× Narita, Akimitsu× Müllen, Klaus× Chi, Lifeng |
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書誌情報 |
en : Journal of the American Chemical Society 巻 141, 号 18, p. 7399-7406, 発行日 2019-04-16 |
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抄録 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Controlling the regioselectivity of C-H activation in unimolecular reactions is of great significance for the rational synthesis of functional graphene nanostructures, which are called nanographenes. Here, we demonstrate that the adsorption of tetranaphthyl-p-terphenyl precursors on metal surfaces can completely change the cyclodehydrogenation route and lead to obtaining planar benzo-fused perihexacenes rather than double [7]helicenes during solution synthesis. The course of the on-surface planarization reactions is monitored using scanning probe microscopy, which unambiguously reveals the formation of dibenzoperihexacenes and the structures of reaction intermediates. The regioselective planarization can be attributed to the flattened adsorption geometries and the reduced flexibility of the precursors on the surfaces, in addition to the different mechanism of the on-surface cyclodehydrogenation from that of the solution counterpart. We have further achieved the on-surface synthesis of dibenzoperioctacene by employing a tetra-anthryl-p-terphenyl precursor. The energy gaps of the new nanographenes are measured to be approximately 2.1 eV (dibenzoperihexacene) and 1.3 eV (dibenzoperioctacene) on a Au(111) surface. Our findings shed new light on the regioselectivity in cyclodehydrogenation reactions, which will be important for exploring the synthesis of unprecedented nanographenes. | |||||
出版者 | ||||||
出版者 | American Chemical Society | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 0002-7863 | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1520-5126 | |||||
PubMed番号 | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | PMID | |||||
関連識別子 | info:pmid/31016976 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | info:doi/10.1021/jacs.9b01267 | |||||
権利 | ||||||
権利情報 | © 2019 American Chemical Society | |||||
権利 | ||||||
権利情報 | ACS AuthorChoice with CC-BY license | |||||
情報源 | ||||||
関連名称 | https://creativecommons.org/licenses/by/4.0/ | |||||
関連サイト | ||||||
識別子タイプ | URI | |||||
関連識別子 | https://pubs.acs.org/doi/10.1021/jacs.9b01267 | |||||
著者版フラグ | ||||||
出版タイプ | VoR | |||||
出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 |