{"@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/1360002216659932416.json","@type":"Article","productIdentifier":[{"identifier":{"@type":"DOI","@value":"10.1021/jacs.5b03118"}},{"identifier":{"@type":"URI","@value":"https://pubs.acs.org/doi/pdf/10.1021/jacs.5b03118"}},{"identifier":{"@type":"PMID","@value":"26028308"}}],"resourceType":"学術雑誌論文(journal article)","dc:title":[{"@value":"Synthesis, Structures, and Properties of π-Extended Double Helicene: A Combination of Planar and Nonplanar π-Systems"}],"description":[{"notation":[{"@value":"The synthesis, structures, and properties of a π-extended double helicene 1 are described. This double helicene 1 was synthesized by a four-fold oxidative C-H biphenylation of naphthalene followed by the Scholl reaction or via five steps including the Suzuki-Miyaura cross-coupling reaction and the Scholl reaction. Due to the two helical substructures, 1 has three isomers, i.e., two enantiomers in a twisted form [(P,P) and (M,M)] and one diastereoisomer in a meso form. X-ray crystallographic analysis of the twisted isomers (twisted-1) revealed a tightly offset packing pattern of (P,P)- and (M,M)-twisted isomers, affording a three-dimensional lamellar stacking structure. A high isomerization barrier (43.5 kcal mol(-1)) and the relative thermal stability of twisted-1 isomer over meso-1 by 0.9 kcal mol(-1) were estimated by DFT calculations. The three isomers were successfully separated by chiral HPLC and characterized by circular dichroism spectroscopy as well as by TD-DFT studies. Electronic state variation resulting from the molecular geometry difference between the two diastereoisomers (twisted-1 and meso-1) was observed by UV-vis absorption and fluorescence spectra."}]}],"creator":[{"@id":"https://cir.nii.ac.jp/crid/1380566394799964032","@type":"Researcher","foaf:name":[{"@value":"Takao Fujikawa"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Science, ‡JST, ERATO, Itami Molecular Nanocarbon Project, and §Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Nagoya 464-8602, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380566394799964034","@type":"Researcher","foaf:name":[{"@value":"Yasutomo Segawa"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Science, ‡JST, ERATO, Itami Molecular Nanocarbon Project, and §Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Nagoya 464-8602, Japan"}]},{"@id":"https://cir.nii.ac.jp/crid/1380566394799964033","@type":"Researcher","foaf:name":[{"@value":"Kenichiro Itami"}],"jpcoar:affiliationName":[{"@value":"Graduate School of Science, ‡JST, ERATO, Itami Molecular Nanocarbon Project, and §Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Nagoya 464-8602, Japan"}]}],"publication":{"publicationIdentifier":[{"@type":"PISSN","@value":"00027863"},{"@type":"EISSN","@value":"15205126"}],"prism:publicationName":[{"@value":"Journal of the American Chemical Society"}],"dc:publisher":[{"@value":"American Chemical Society (ACS)"}],"prism:publicationDate":"2015-06-11","prism:volume":"137","prism:number":"24","prism:startingPage":"7763","prism:endingPage":"7768"},"reviewed":"false","url":[{"@id":"https://pubs.acs.org/doi/pdf/10.1021/jacs.5b03118"}],"createdAt":"2015-06-01","modifiedAt":"2024-06-09","foaf:topic":[{"@id":"https://cir.nii.ac.jp/all?q=Models,%20Molecular","dc:title":"Models, Molecular"},{"@id":"https://cir.nii.ac.jp/all?q=Biphenyl%20Compounds","dc:title":"Biphenyl Compounds"},{"@id":"https://cir.nii.ac.jp/all?q=Naphthalenes","dc:title":"Naphthalenes"},{"@id":"https://cir.nii.ac.jp/all?q=Crystallography,%20X-Ray","dc:title":"Crystallography, X-Ray"},{"@id":"https://cir.nii.ac.jp/all?q=Isomerism","dc:title":"Isomerism"},{"@id":"https://cir.nii.ac.jp/all?q=Quantum%20Theory","dc:title":"Quantum Theory"},{"@id":"https://cir.nii.ac.jp/all?q=Thermodynamics","dc:title":"Thermodynamics"},{"@id":"https://cir.nii.ac.jp/all?q=Polycyclic%20Compounds","dc:title":"Polycyclic Compounds"},{"@id":"https://cir.nii.ac.jp/all?q=Oxidation-Reduction","dc:title":"Oxidation-Reduction"}],"project":[{"@id":"https://cir.nii.ac.jp/crid/1040282256774671104","@type":"Project","projectIdentifier":[{"@type":"KAKEN","@value":"14J10460"},{"@type":"JGN","@value":"JP14J10460"},{"@type":"URI","@value":"https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-14J10460/"}],"notation":[{"@language":"ja","@value":"三次元周期構造をもつ新奇ナノカーボン物質の創成"}]}],"relatedProduct":[{"@id":"https://cir.nii.ac.jp/crid/1050001338805862656","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"Synthesis, properties, and crystal structures of π-extended double [6]helicenes: contorted multi-dimensional stacking lattice"}]},{"@id":"https://cir.nii.ac.jp/crid/1050001338805989760","@type":"Article","resourceType":"学術雑誌論文(journal article)","relationType":["isReferencedBy"],"jpcoar:relatedTitle":[{"@language":"en","@value":"A Quintuple 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