Trapping of Stable [4n+1] pi-Electron Species from Peripherally Substituted, Conformationally Rigid, Antiaromatic Hexaphyrins

Cited 5 time in webofscience Cited 0 time in scopus
  • Hit : 110
  • Download : 0
DC FieldValueLanguage
dc.contributor.authorFirmansyah, Dikhiko
dc.contributor.authorHong, Seong-Jinko
dc.contributor.authorDutta, Ranjanko
dc.contributor.authorHe, Qingko
dc.contributor.authorBae, Jinheeko
dc.contributor.authorJo, Hongilko
dc.contributor.authorKim, Hakwonko
dc.contributor.authorOk, Kang Minko
dc.contributor.authorLynch, Vincent M.ko
dc.contributor.authorByon, Hye Ryungko
dc.contributor.authorSessler, Jonathan L.ko
dc.contributor.authorLee, Chang-Heeko
dc.date.accessioned2019-04-15T14:16:03Z-
dc.date.available2019-04-15T14:16:03Z-
dc.date.created2019-03-26-
dc.date.issued2019-03-
dc.identifier.citationCHEMISTRY-A EUROPEAN JOURNAL, v.25, no.14, pp.3525 - 3531-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10203/254008-
dc.description.abstractPeripherally substituted antiaromatic naphthorosarins have been synthesized for the first time. The synthesis was accomplished by acid-catalyzed condensation of naphthobipyrrole building blocks with aromatic aldehydes. The naphthobipyrrole building blocks were synthesized by simple oxidative coupling of the corresponding pyrrole substituted aromatics. Solid-state structural analyses of the synthesized naphthorosarins revealed that the presence of meso-2,6-dichlorophenyl- and 5,6-difluoro-substitution substantially alter the geometry and properties of the naphthorosarins. The substituents affect the redox potentials as well and, in turn, the proton-coupled electron-transfer processes leading to the formation of one- and two-electron reduced forms of the corresponding naphthorosarins. One particular naphthorosarin that bears both peripheral fluorine and meso-2,6-dichlorophenyl substituents forms a stable 25 pi-electron species upon treating with TFA that was characterized by single-crystal X-ray diffraction analysis. The current study underscores how structural modifications can be used to fine-tune the electronic features of naphthorosarins, including stabilization of odd electron species.-
dc.languageEnglish-
dc.publisherWILEY-V C H VERLAG GMBH-
dc.titleTrapping of Stable [4n+1] pi-Electron Species from Peripherally Substituted, Conformationally Rigid, Antiaromatic Hexaphyrins-
dc.typeArticle-
dc.identifier.wosid000460692100015-
dc.identifier.scopusid2-s2.0-85061603815-
dc.type.rimsART-
dc.citation.volume25-
dc.citation.issue14-
dc.citation.beginningpage3525-
dc.citation.endingpage3531-
dc.citation.publicationnameCHEMISTRY-A EUROPEAN JOURNAL-
dc.identifier.doi10.1002/chem.201900022-
dc.contributor.localauthorByon, Hye Ryung-
dc.contributor.nonIdAuthorFirmansyah, Dikhi-
dc.contributor.nonIdAuthorHong, Seong-Jin-
dc.contributor.nonIdAuthorDutta, Ranjan-
dc.contributor.nonIdAuthorHe, Qing-
dc.contributor.nonIdAuthorBae, Jinhee-
dc.contributor.nonIdAuthorJo, Hongil-
dc.contributor.nonIdAuthorKim, Hakwon-
dc.contributor.nonIdAuthorOk, Kang Min-
dc.contributor.nonIdAuthorLynch, Vincent M.-
dc.contributor.nonIdAuthorSessler, Jonathan L.-
dc.contributor.nonIdAuthorLee, Chang-Hee-
dc.description.isOpenAccessN-
dc.type.journalArticleArticle-
dc.subject.keywordAuthorantiaromatic-
dc.subject.keywordAuthorexpanded porphyrins-
dc.subject.keywordAuthornaphthorosarin-
dc.subject.keywordAuthorperipheral substitution-
dc.subject.keywordAuthorredox potential-
dc.subject.keywordAuthorstable radical cation (25pi)-
dc.subject.keywordPlusEXPANDED PORPHYRINS-
dc.subject.keywordPlusNAPHTHOBIPYRROLE-
dc.subject.keywordPlusROSARIN-
Appears in Collection
CH-Journal Papers(저널논문)
Files in This Item
There are no files associated with this item.
This item is cited by other documents in WoS
⊙ Detail Information in WoSⓡ Click to see webofscience_button
⊙ Cited 5 items in WoS Click to see citing articles in records_button

qr_code

  • mendeley

    citeulike


rss_1.0 rss_2.0 atom_1.0