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Synthesis and Characterizations of 5,5′‐Bibenzo[rst]pentaphene with Axial Chirality and Symmetry‐Breaking Charge Transfer
https://oist.repo.nii.ac.jp/records/2585
https://oist.repo.nii.ac.jp/records/25855026e751-039c-4d93-ad4e-fe4e425487d6
名前 / ファイル | ライセンス | アクション |
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Advanced Science - 2022 - Xu - Synthesis and C (2.2 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 | 2022-03-08 | |||||
タイトル | ||||||
言語 | en | |||||
タイトル | Synthesis and Characterizations of 5,5′‐Bibenzo[rst]pentaphene with Axial Chirality and Symmetry‐Breaking Charge Transfer | |||||
言語 | ||||||
言語 | eng | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | axial chirality | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | benzo[rst]pentaphene | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | biaryl | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | symmetry-breaking charge transfer | |||||
キーワード | ||||||
言語 | en | |||||
主題Scheme | Other | |||||
主題 | transient absorption | |||||
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) |
Xu, Xiushang
× Xu, Xiushang× Gunasekaran, Suman× Renken, Scott× Ripani, Lorenzo× Schollmeyer, Dieter× Kim, Woojae× Marcaccio, Massimo× Musser, Andrew× Narita, Akimitsu |
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書誌情報 |
en : Advanced Science p. 2200004, 発行日 2022-02-13 |
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抄録 | ||||||
内容記述タイプ | Other | |||||
内容記述 | Exploration of novel biaryls consisting of two polycyclic aromatic hydrocarbon (PAH) units can be an important strategy toward further developments of organic materials with unique properties. In this study, 5,5′-bibenzo[rst]pentaphene (BBPP) with two benzo[rst]pentaphene (BPP) units is synthesized in an efficient and versatile approach, and its structure is unambiguously elucidated by X-ray crystallography. BBPP exhibits axial chirality, and the (M)- and (P)-enantiomers are resolved by chiral high-performance liquid chromatography and studied by circular dichroism spectroscopy. These enantiomers have a relatively high isomerization barrier of 43.6 kcal mol⁻¹ calculated by density functional theory. The monomer BPP and dimer BBPP are characterized by UV-vis absorption and fluorescence spectroscopy, cyclic voltammetry, and femtosecond transient absorption spectroscopy. The results indicate that both BPP and BBPP fluoresce from a formally dark S₁ electronic state that is enabled by Herzberg–Teller intensity borrowing from a neighboring bright S₂ state. While BPP exhibits a relatively low photoluminescence quantum yield (PLQY), BBPP exhibits a significantly enhanced PLQY due to a greater S₂ intensity borrowing. Moreover, symmetry-breaking charge transfer in BBPP is demonstrated by spectroscopic investigations in solvents of different polarity. This suggests high potential for singlet fission in such π-extended biaryls through appropriate molecular design. | |||||
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 | 2198-3844 | |||||
PubMed番号 | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | PMID | |||||
関連識別子 | info:pmid/35156332 | |||||
DOI | ||||||
関連タイプ | isIdenticalTo | |||||
識別子タイプ | DOI | |||||
関連識別子 | info:doi/10.1002/advs.202200004 | |||||
権利 | ||||||
権利情報 | © 2022 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/advs.202200004 | |||||
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 |