{"created":"2023-06-26T11:01:49.701734+00:00","id":2585,"links":{},"metadata":{"_buckets":{"deposit":"8752ee30-63b1-4bec-843c-4d6b882ed5fc"},"_deposit":{"created_by":32,"id":"2585","owners":[32],"pid":{"revision_id":0,"type":"depid","value":"2585"},"status":"published"},"_oai":{"id":"oai:oist.repo.nii.ac.jp:00002585","sets":["6:177"]},"author_link":["16830","16826","16828","16822","16823","16827","16829","16824","16825"],"item_10001_biblio_info_7":{"attribute_name":"Bibliographic Information","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2022-02-13","bibliographicIssueDateType":"Issued"},"bibliographicPageStart":"2200004","bibliographic_titles":[{},{"bibliographic_title":"Advanced Science","bibliographic_titleLang":"en"}]}]},"item_10001_creator_3":{"attribute_name":"Author","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Xu, Xiushang"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Gunasekaran, Suman"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Renken, Scott"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Ripani, Lorenzo"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Schollmeyer, Dieter"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Kim, Woojae"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Marcaccio, Massimo"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Musser, Andrew"}],"nameIdentifiers":[{}]},{"creatorNames":[{"creatorName":"Narita, Akimitsu"}],"nameIdentifiers":[{}]}]},"item_10001_description_5":{"attribute_name":"Abstract","attribute_value_mlt":[{"subitem_description":"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.","subitem_description_type":"Other"}]},"item_10001_publisher_8":{"attribute_name":"Publisher","attribute_value_mlt":[{"subitem_publisher":"Wiley-VCH GmbH"}]},"item_10001_relation_13":{"attribute_name":"PubMedNo.","attribute_value_mlt":[{"subitem_relation_type":"isIdenticalTo","subitem_relation_type_id":{"subitem_relation_type_id_text":"info:pmid/35156332","subitem_relation_type_select":"PMID"}}]},"item_10001_relation_14":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type":"isIdenticalTo","subitem_relation_type_id":{"subitem_relation_type_id_text":"info:doi/10.1002/advs.202200004","subitem_relation_type_select":"DOI"}}]},"item_10001_relation_17":{"attribute_name":"Related site","attribute_value_mlt":[{"subitem_relation_type_id":{"subitem_relation_type_id_text":"https://onlinelibrary.wiley.com/doi/10.1002/advs.202200004","subitem_relation_type_select":"URI"}}]},"item_10001_rights_15":{"attribute_name":"Rights","attribute_value_mlt":[{"subitem_rights":"© 2022 The Author(s)."}]},"item_10001_source_id_9":{"attribute_name":"ISSN","attribute_value_mlt":[{"subitem_source_identifier":"2198-3844","subitem_source_identifier_type":"ISSN"}]},"item_10001_version_type_20":{"attribute_name":"Author's flag","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_970fb48d4fbd8a85","subitem_version_type":"VoR"}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2022-03-08"}],"displaytype":"detail","filename":"Advanced Science - 2022 - Xu - Synthesis and C.pdf","filesize":[{"value":"2.2 MB"}],"format":"application/pdf","license_note":"Creative Commons Attribution 4.0 International(https://creativecommons.org/licenses/by/4.0/)","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"Advanced Science - 2022 - Xu - Synthesis and C","url":"https://oist.repo.nii.ac.jp/record/2585/files/Advanced Science - 2022 - Xu - Synthesis and C.pdf"},"version_id":"038e621a-9c32-49e9-991c-0d8cf6891e39"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"axial chirality","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"benzo[rst]pentaphene","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"biaryl","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"symmetry-breaking charge transfer","subitem_subject_language":"en","subitem_subject_scheme":"Other"},{"subitem_subject":"transient absorption","subitem_subject_language":"en","subitem_subject_scheme":"Other"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"Synthesis and Characterizations of 5,5′‐Bibenzo[rst]pentaphene with Axial Chirality and Symmetry‐Breaking Charge Transfer","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"Synthesis and Characterizations of 5,5′‐Bibenzo[rst]pentaphene with Axial Chirality and Symmetry‐Breaking Charge Transfer","subitem_title_language":"en"}]},"item_type_id":"10001","owner":"32","path":["177"],"pubdate":{"attribute_name":"公開日","attribute_value":"2022-03-08"},"publish_date":"2022-03-08","publish_status":"0","recid":"2585","relation_version_is_last":true,"title":["Synthesis and Characterizations of 5,5′‐Bibenzo[rst]pentaphene with Axial Chirality and Symmetry‐Breaking Charge Transfer"],"weko_creator_id":"32","weko_shared_id":32},"updated":"2023-06-26T11:28:27.590261+00:00"}