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Dicyclopentaannelated Hexa-peri-hexabenzocoronenes with a Singlet Biradical Ground State
https://oist.repo.nii.ac.jp/records/2031
https://oist.repo.nii.ac.jp/records/20317658f09f-6303-47a1-9ac0-f344cb944637
名前 / ファイル | ライセンス | アクション |
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anie.202102932 (1.6 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 | 2021-05-06 | |||||
タイトル | ||||||
タイトル | Dicyclopentaannelated Hexa-peri-hexabenzocoronenes with a Singlet Biradical Ground State | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | dicyclopentaannelation | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | hexa-peri-hexabenzocoronene | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | low energy gap | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | not-fully benzenoid PAH | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | open-shell biradical | |||||
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) |
Chen, Qiang
× Chen, Qiang× Baumgarten, Martin× Wagner, Manfred× Hu, Yunbin× Hou, Ian Cheng‐Yi× Narita, Akimitsu× Müllen, Klaus |
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書誌情報 |
en : Angewandte Chemie International Edition 巻 60, 号 20, p. 11300-11304, 発行日 2021-04-07 |
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抄録 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Synthesis of two dicyclopentaannelated hexa-peri-hexabenzocoronene (PHBC) regioisomers was carried out, using nonplanar oligoaryl precursors with fluorenyl groups: mPHBC 8 with two pentagons in the "meta"-configuration was obtained as a stable molecule, while its structural isomer with the "para"-configuration, pPHBC 16, could be generated and characterized only in situ due to its high chemical reactivity. Both PHBCs exhibit low energy gaps, as reflected by UV-vis-NIR absorption and electrochemical measurements. They also show open-shell singlet ground states according to electron paramagnetic resonance (EPR) measurements and density functional theory (DFT) calculations. The use of fully benzenoid HBC as a bridging moiety leads to significant singlet biradical characters (y₀) of 0.72 and 0.96 for mPHBC 8 and pPHBC 16, respectively, due to the strong rearomatization tendency of the HBC pi-system; these values are among the highest for planar carbon-centered biradical molecules. The incorporation of fully unsaturated pentagons strongly perturbs the aromaticity of the parent HBC and makes the constituted benzene rings less aromatic or antiaromatic. These results illustrate the high impact of cyclopentaannelation on the electronic structures of fully benzenoid polycyclic aromatic hydrocarbons (PAHs) and open up a new avenue towards open-shell PAHs with prominent singlet biradical characters. | |||||
出版者 | ||||||
出版者 | Wiley-VCH GmbH | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1433-7851 | |||||
ISSN | ||||||
収録物識別子タイプ | ISSN | |||||
収録物識別子 | 1521-3773 | |||||
PubMed番号 | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | PMID | |||||
関連識別子 | info:pmid/33749985 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | info:doi/10.1002/anie.202102932 | |||||
権利 | ||||||
権利情報 | © 2021 The Author(s). | |||||
関連サイト | ||||||
識別子タイプ | URI | |||||
関連識別子 | https://onlinelibrary.wiley.com/doi/10.1002/anie.202102932 | |||||
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 |