{"@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/1362825894522943616.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1021/acs.accounts.9b00322"}},{"identifier":{"@type":"URI","@value":"http://pubs.acs.org/doi/pdf/10.1021/acs.accounts.9b00322"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/acs.accounts.9b00322"}},{"identifier":{"@type":"PMID","@value":"31478641"}},{"identifier":{"@type":"HANDLE","@value":"21.11116/0000-0004-C117-8"}},{"identifier":{"@type":"HANDLE","@value":"21.11116/0000-0004-C115-A"}}],"dc:title":[{"@value":"Heteroatom-Doped Nanographenes with Structural Precision"}],"description":[{"notation":[{"@value":"Nanographenes, which are defined as nanoscale (1-100 nm) graphene cutouts, include quasi-one-dimensional graphene nanoribbons (GNRs) and quasi-zero-dimensional graphene quantum dots (GQDs). Polycyclic aromatic hydrocarbons (PAHs) larger than 1 nm can be viewed as GQDs with atomically precise molecular structures and can thus be termed nanographene molecules. As a result of quantum confinement, nanographenes are promising for next-generation semiconductor applications with finite band gaps, a significant advantage compared with gapless two-dimensional graphene. Similar to the atomic doping strategy in inorganic semiconductors, incorporation of heteroatoms into nanographenes is a viable way to tune their optical, electronic, catalytic, and magnetic properties. Such properties are highly dependent not only on the molecular size and edge structure but also on the heteroatom type, doping position, and concentration. Therefore, reliable synthetic methods are required to precisely control these structural features. In this regard, bottom-up organic synthesis provides an indispensable way to achieve structurally well-defined heteroatom-doped nanographenes. Polycyclic heteroaromatic compounds have attracted great attention of organic chemists for decades. Research in this direction has been further promoted by modern interest in supramolecular chemistry and organic electronics. The rise of graphene in the 21st century has endowed large polycyclic heteroaromatic compounds with a new role as model systems for heteroatom-doped graphene. Heteroatom-doped nanographene molecules are in their own right promising materials for photonic, optoelectronic, and spintronic applications because of the extended π conjugation. Despite the significant advances in polycyclic heteroaromatic compounds, heteroatom-doped nanographene molecules with sizes of over 1 nm and their relevant GNRs are still scarce. In this Account, we describe the synthesis and properties of large heteroatom-doped nanographenes, mainly summarizing relevant advances in our group in the past decade. We first present several examples of heteroatom doping based on the prototypical nanographene molecule, i.e., hexa-"}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1382825894522943619","@type":"Researcher","foaf:name":[{"@value":"Xiao-Ye Wang"}],"jpcoar:affiliationName":[{"@value":"State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China"},{"@value":"Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825894522943618","@type":"Researcher","foaf:name":[{"@value":"Xuelin Yao"}],"jpcoar:affiliationName":[{"@value":"Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825894522943617","@type":"Researcher","foaf:name":[{"@value":"Akimitsu Narita"}],"jpcoar:affiliationName":[{"@value":"Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany"},{"@value":"Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, Okinawa 904-0495, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1382825894522943616","@type":"Researcher","foaf:name":[{"@value":"Klaus Müllen"}],"jpcoar:affiliationName":[{"@value":"Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00014842"},{"@type":"EISSN","@value":"15204898"}],"prism:publicationName":[{"@value":"Accounts of Chemical Research"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"2019-09-03","prism:volume":"52","prism:number":"9","prism:startingPage":"2491","prism:endingPage":"2505"},"reviewed":"false","dcterms:accessRights":"http://purl.org/coar/access_right/c_abf2","dc:rights":["http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html"],"url":[{"@id":"http://pubs.acs.org/doi/pdf/10.1021/acs.accounts.9b00322"},{"@id":"https://pubs.acs.org/doi/pdf/10.1021/acs.accounts.9b00322"}],"createdAt":"2019-09-03","modifiedAt":"2023-04-17","relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050006210047802240","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Pillar[6]arene acts as a biosensor for quantitative detection of a vitamin metabolite in crude biological samples"}]},{"@id":"https://cir.nii.ac.jp/crid/1050021868454167424","@type":"Article","resourceType":"学術雑誌論文(journal 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