{"@context":{"@vocab":"https://cir.nii.ac.jp/schema/1.0/","rdfs":"http://www.w3.org/2000/01/rdf-schema#","dc":"http://purl.org/dc/elements/1.1/","dcterms":"http://purl.org/dc/terms/","foaf":"http://xmlns.com/foaf/0.1/","prism":"http://prismstandard.org/namespaces/basic/2.0/","cinii":"http://ci.nii.ac.jp/ns/1.0/","datacite":"https://schema.datacite.org/meta/kernel-4/","ndl":"http://ndl.go.jp/dcndl/terms/","jpcoar":"https://github.com/JPCOAR/schema/blob/master/2.0/"},"@id":"https://cir.nii.ac.jp/crid/1360565166754670592.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1038/nchem.2518"}},{"identifier":{"@type":"URI","@value":"http://www.nature.com/articles/nchem.2518.pdf"}},{"identifier":{"@type":"URI","@value":"http://www.nature.com/articles/nchem.2518"}},{"identifier":{"@type":"PMID","@value":"27442280"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals"}],"description":[{"notation":[{"@value":"The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram scale. The molecular structure was confirmed through single-crystal X-ray diffraction. From variable-temperature Raman spectroscopy and magnetic susceptibility measurements a thermally accessible triplet excited state was found. Organic field-effect transistor device data show an ambipolar performance with balanced electron and hole mobilities. Our results demonstrate the rational design and synthesis of an air- and temperature-stable biradical compound."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380847869920566404","@type":"Researcher","foaf:name":[{"@value":"Kotaro Fukuda"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566410","@type":"Researcher","foaf:name":[{"@value":"Gabriel E. Rudebusch"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566411","@type":"Researcher","foaf:name":[{"@value":"Rocío Ponce Ortiz"}]},{"@id":"https://cir.nii.ac.jp/crid/1420001326213584384","@type":"Researcher","personIdentifier":[{"@type":"KAKEN_RESEARCHERS","@value":"80252568"},{"@type":"NRID","@value":"1000080252568"},{"@type":"CINII_AUTHOR_ID","@value":"DA15436407"},{"@type":"URI","@value":"https://ci.nii.ac.jp/author/DA15436407#entity"},{"@type":"URI","@value":"https://viaf.org/viaf/NII%7CDA15436407"},{"@type":"NRID","@value":"9000391782263"},{"@type":"NRID","@value":"9000239878811"},{"@type":"NRID","@value":"9000256017339"},{"@type":"NRID","@value":"9000007271771"},{"@type":"NRID","@value":"9000286315561"},{"@type":"NRID","@value":"9000408570813"},{"@type":"NRID","@value":"9000256017120"},{"@type":"NRID","@value":"9000242736861"},{"@type":"NRID","@value":"9000333203375"},{"@type":"NRID","@value":"9000392705044"},{"@type":"NRID","@value":"9000392843577"},{"@type":"NRID","@value":"9000252970412"},{"@type":"NRID","@value":"9000391782291"},{"@type":"NRID","@value":"9000000804613"},{"@type":"NRID","@value":"9000392705326"},{"@type":"NRID","@value":"9000251859497"},{"@type":"NRID","@value":"9000401609222"},{"@type":"NRID","@value":"9000259306839"},{"@type":"NRID","@value":"9000396176615"},{"@type":"NRID","@value":"9000007025416"},{"@type":"NRID","@value":"9000252965363"},{"@type":"NRID","@value":"9000401615387"},{"@type":"NRID","@value":"9000392698261"},{"@type":"NRID","@value":"9000347545861"},{"@type":"NRID","@value":"9000391782260"},{"@type":"NRID","@value":"9000258598114"},{"@type":"NRID","@value":"9000252970569"},{"@type":"NRID","@value":"9000265542663"},{"@type":"NRID","@value":"9000367823247"},{"@type":"NRID","@value":"9000001052308"},{"@type":"NRID","@value":"9000002336138"},{"@type":"NRID","@value":"9000327090151"},{"@type":"RESEARCHMAP","@value":"https://researchmap.jp/read0046584"}],"foaf:name":[{"@value":"Masayoshi Nakano"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566413","@type":"Researcher","foaf:name":[{"@value":"Henrik Ottosson"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566408","@type":"Researcher","foaf:name":[{"@value":"Guzmán L. Espejo"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566409","@type":"Researcher","foaf:name":[{"@value":"Juan Casado"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566407","@type":"Researcher","foaf:name":[{"@value":"José L. Zafra"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566403","@type":"Researcher","foaf:name":[{"@value":"Michael M. Haley"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566401","@type":"Researcher","foaf:name":[{"@value":"Jonathan L. Marshall"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566406","@type":"Researcher","foaf:name":[{"@value":"Kjell Jorner"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566402","@type":"Researcher","foaf:name":[{"@value":"Iratxe Arrechea-Marcos"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566412","@type":"Researcher","foaf:name":[{"@value":"Carlos J. Gómez-García"}]},{"@id":"https://cir.nii.ac.jp/crid/1380847869920566400","@type":"Researcher","foaf:name":[{"@value":"Lev N. Zakharov"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"17554330"},{"@type":"EISSN","@value":"17554349"}],"prism:publicationName":[{"@value":"Nature Chemistry"}],"dc:publisher":[{"@value":"Springer Science and Business Media LLC"}],"prism:publicationDate":"2016-05-23","prism:volume":"8","prism:number":"8","prism:startingPage":"753","prism:endingPage":"759"},"reviewed":"false","dc:rights":["http://www.springer.com/tdm"],"url":[{"@id":"http://www.nature.com/articles/nchem.2518.pdf"},{"@id":"http://www.nature.com/articles/nchem.2518"}],"createdAt":"2016-05-24","modifiedAt":"2023-08-18","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Anthracenes","dc:title":"Anthracenes"},{"@id":"https://cir.nii.ac.jp/all?q=Models,%20Molecular","dc:title":"Models, Molecular"},{"@id":"https://cir.nii.ac.jp/all?q=Free%20Radicals","dc:title":"Free Radicals"},{"@id":"https://cir.nii.ac.jp/all?q=Molecular%20Structure","dc:title":"Molecular Structure"},{"@id":"https://cir.nii.ac.jp/all?q=Chemistry,%20Organic","dc:title":"Chemistry, Organic"},{"@id":"https://cir.nii.ac.jp/all?q=Temperature","dc:title":"Temperature"},{"@id":"https://cir.nii.ac.jp/all?q=Electrons","dc:title":"Electrons"},{"@id":"https://cir.nii.ac.jp/all?q=Crystallography,%20X-Ray","dc:title":"Crystallography, X-Ray"},{"@id":"https://cir.nii.ac.jp/all?q=Magnetics","dc:title":"Magnetics"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040000782278889728","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"26107004"},{"@type":"JGN","@value":"JP26107004"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PLANNED-26107004/"}],"notation":[{"@language":"ja","@value":"理論と実験の協奏的アプローチによる複合スピン励起子変換制御"},{"@language":"en","@value":"Control of multiple spin exciton states by synergetic studies of theory and 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and Reactions of Stimuli-responsive High-coordinate Main Group Element Compounds"}]},{"@id":"https://cir.nii.ac.jp/crid/1040282257215448320","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"25248007"},{"@type":"JGN","@value":"JP25248007"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-25248007/"}],"notation":[{"@language":"ja","@value":"マルチラジカル性を有する開殻超分子系の光磁気機能物質の創成"},{"@language":"en","@value":"Creation of open-shell supramolecular optical and magnetic functional materials with multiradical character"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050581168899711360","@type":"Article","resourceType":"会議発表資料(conference paper)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Closed-shell and open-shell dual nature of singlet diradical compounds"}]},{"@id":"https://cir.nii.ac.jp/crid/1050845763736961408","@type":"Article","resourceType":"学術雑誌論文(journal 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