DC Field | Value | Language |
---|---|---|
dc.contributor.author | Firmansyah, Dikhi | ko |
dc.contributor.author | Hong, Seong-Jin | ko |
dc.contributor.author | Dutta, Ranjan | ko |
dc.contributor.author | He, Qing | ko |
dc.contributor.author | Bae, Jinhee | ko |
dc.contributor.author | Jo, Hongil | ko |
dc.contributor.author | Kim, Hakwon | ko |
dc.contributor.author | Ok, Kang Min | ko |
dc.contributor.author | Lynch, Vincent M. | ko |
dc.contributor.author | Byon, Hye Ryung | ko |
dc.contributor.author | Sessler, Jonathan L. | ko |
dc.contributor.author | Lee, Chang-Hee | ko |
dc.date.accessioned | 2019-04-15T14:16:03Z | - |
dc.date.available | 2019-04-15T14:16:03Z | - |
dc.date.created | 2019-03-26 | - |
dc.date.issued | 2019-03 | - |
dc.identifier.citation | CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.14, pp.3525 - 3531 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10203/254008 | - |
dc.description.abstract | Peripherally 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.language | English | - |
dc.publisher | WILEY-V C H VERLAG GMBH | - |
dc.title | Trapping of Stable [4n+1] pi-Electron Species from Peripherally Substituted, Conformationally Rigid, Antiaromatic Hexaphyrins | - |
dc.type | Article | - |
dc.identifier.wosid | 000460692100015 | - |
dc.identifier.scopusid | 2-s2.0-85061603815 | - |
dc.type.rims | ART | - |
dc.citation.volume | 25 | - |
dc.citation.issue | 14 | - |
dc.citation.beginningpage | 3525 | - |
dc.citation.endingpage | 3531 | - |
dc.citation.publicationname | CHEMISTRY-A EUROPEAN JOURNAL | - |
dc.identifier.doi | 10.1002/chem.201900022 | - |
dc.contributor.localauthor | Byon, Hye Ryung | - |
dc.contributor.nonIdAuthor | Firmansyah, Dikhi | - |
dc.contributor.nonIdAuthor | Hong, Seong-Jin | - |
dc.contributor.nonIdAuthor | Dutta, Ranjan | - |
dc.contributor.nonIdAuthor | He, Qing | - |
dc.contributor.nonIdAuthor | Bae, Jinhee | - |
dc.contributor.nonIdAuthor | Jo, Hongil | - |
dc.contributor.nonIdAuthor | Kim, Hakwon | - |
dc.contributor.nonIdAuthor | Ok, Kang Min | - |
dc.contributor.nonIdAuthor | Lynch, Vincent M. | - |
dc.contributor.nonIdAuthor | Sessler, Jonathan L. | - |
dc.contributor.nonIdAuthor | Lee, Chang-Hee | - |
dc.description.isOpenAccess | N | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordAuthor | antiaromatic | - |
dc.subject.keywordAuthor | expanded porphyrins | - |
dc.subject.keywordAuthor | naphthorosarin | - |
dc.subject.keywordAuthor | peripheral substitution | - |
dc.subject.keywordAuthor | redox potential | - |
dc.subject.keywordAuthor | stable radical cation (25pi) | - |
dc.subject.keywordPlus | EXPANDED PORPHYRINS | - |
dc.subject.keywordPlus | NAPHTHOBIPYRROLE | - |
dc.subject.keywordPlus | ROSARIN | - |
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