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dc.contributor.author | Umetani, Masataka | en |
dc.contributor.author | Tanaka, Takayuki | en |
dc.contributor.author | Osuka, Atsuhiro | en |
dc.contributor.alternative | 梅谷, 将隆 | ja |
dc.contributor.alternative | 田中, 隆行 | ja |
dc.contributor.alternative | 大須賀, 篤弘 | ja |
dc.date.accessioned | 2018-11-02T05:36:18Z | - |
dc.date.available | 2018-11-02T05:36:18Z | - |
dc.date.issued | 2018-01-01 | - |
dc.identifier.issn | 2041-6520 | - |
dc.identifier.uri | http://hdl.handle.net/2433/234933 | - |
dc.description.abstract | A new motif for artificial double helices was developed on the basis of α, α′-disubstituted tripyrrin. α, α′-Dibromotripyrrin 3 was prepared by gentle bromination at the pyrrolic α-positions of 5, 10-diphenyltripyrrane followed by oxidation with DDQ. Nucleophilic substitution reactions of 3 with anilines proceeded efficiently to furnish a series of α, α′-dianilinotripyrrins 4–11, which displayed monomeric and dimeric forms depending upon the solvent used for crystallization and the structures of the substituted anilines. Dimeric forms show double helical structures with smooth π-conjugation as indicated by their absorption spectra. van't-Hoff plot analyses revealed that the dimerizations in CDCl3 are enthalpy-driven. Larger association constants of the dimerization are attained for 3, 5-di-t-butylanilino- and 3, 5-bis(trifluoromethyl)anilino-substituted tripyrrins (7 and 8) via additional multiple intermolecular interactions. In a nonpolar and aprotic solvent, tripyrrins (9 and 10) bearing bulkier 1-naphthylamino and mesitylamino groups do not dimerize but undergo unique tautomerization. | en |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Royal Society of Chemistry | en |
dc.rights | © The Royal Society of Chemistry 2018. This Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licence. | en |
dc.title | Conjugated double helices via self-dimerization of α,α′-dianilinotripyrrins | en |
dc.type | journal article | - |
dc.type.niitype | Journal Article | - |
dc.identifier.jtitle | Chemical Science | en |
dc.identifier.volume | 9 | - |
dc.identifier.spage | 6853 | - |
dc.identifier.epage | 6859 | - |
dc.relation.doi | 10.1039/c8sc02739k | - |
dc.textversion | publisher | - |
dc.address | Department of Chemistry, Graduate School of Science, Kyoto University | en |
dc.address | Department of Chemistry, Graduate School of Science, Kyoto University | en |
dc.address | Department of Chemistry, Graduate School of Science, Kyoto University | en |
dc.identifier.pmid | 30310618 | - |
dcterms.accessRights | open access | - |
datacite.awardNumber | JP26810021 | - |
datacite.awardNumber | JP18H03910 | - |
datacite.awardNumber | JP18K14199 | - |
jpcoar.funderName | 日本学術振興会 | ja |
jpcoar.funderName | 日本学術振興会 | ja |
jpcoar.funderName | 日本学術振興会 | ja |
jpcoar.funderName.alternative | Japan Society for the Promotion of Science (JSPS) | en |
jpcoar.funderName.alternative | Japan Society for the Promotion of Science (JSPS) | en |
jpcoar.funderName.alternative | Japan Society for the Promotion of Science (JSPS) | en |
出現コレクション: | 学術雑誌掲載論文等 |
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