Protonation-coupled redox reactions in planar antiaromatic meso-pentafluorophenyl-substituted o-phenylene-bridged annulated rosarins
DC Field | Value | Language |
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dc.contributor.author | Ishida, Masatoshi | - |
dc.contributor.author | Kim, Soo-Jin | - |
dc.contributor.author | Preihs, Christian | - |
dc.contributor.author | Ohkubo, Kei | - |
dc.contributor.author | Lim, Jong Min | - |
dc.contributor.author | Lee, Byung Sun | - |
dc.contributor.author | Park, Jung Su | - |
dc.contributor.author | Lynch, Vincent M. | - |
dc.contributor.author | Roznyatovskiy, Vladimir V. | - |
dc.contributor.author | Sarma, Tridib | - |
dc.contributor.author | Panda, Pradeepta K. | - |
dc.contributor.author | Lee, Chang-Hee | - |
dc.contributor.author | Fukuzumi, Shunichi | - |
dc.contributor.author | Kim, Dongho | - |
dc.contributor.author | Sessler, Jonathan L. | - |
dc.date.accessioned | 2022-04-19T10:21:43Z | - |
dc.date.available | 2022-04-19T10:21:43Z | - |
dc.date.issued | 2013-01 | - |
dc.identifier.issn | 1755-4330 | - |
dc.identifier.issn | 1755-4349 | - |
dc.identifier.uri | https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/147512 | - |
dc.description.abstract | Proton-coupled electron transfer (PCET) processes are among the most important phenomena that control a variety of chemical and biological transformations. Although extensively studied in a variety of natural systems and discrete metal complexes, PCET mechanisms are less well codified in the case of purely organic compounds. Here we report that a planar beta,beta'-phenylene-bridged hexaphyrin (1.0.1.0.1.0), a 24 pi-electron antiaromatic species termed rosarin, displays unique redox reactivity on protonation. Specifically, treatment with acid (for example, HI) yields a 26 pi-electron aromatic triprotonated monocationic species that is produced spontaneously via an intermediate-but stable-25 pi-electron non-aromatic triprotonated monoradical dication. This latter species is also produced on treatment of the original 24 pi-electron antiaromatic starting material with HCl or HBr. The stepwise nature of the proton-coupled reduction observed in the planar rosarin stands in marked contrast to that seen for non-annulated rosarins and other ostensibly antiaromatic expanded porphyrinoids. | - |
dc.format.extent | 6 | - |
dc.language | 영어 | - |
dc.language.iso | ENG | - |
dc.publisher | NATURE PUBLISHING GROUP | - |
dc.title | Protonation-coupled redox reactions in planar antiaromatic meso-pentafluorophenyl-substituted o-phenylene-bridged annulated rosarins | - |
dc.type | Article | - |
dc.publisher.location | 영국 | - |
dc.identifier.doi | 10.1038/NCHEM.1501 | - |
dc.identifier.scopusid | 2-s2.0-84871555914 | - |
dc.identifier.wosid | 000312592300007 | - |
dc.identifier.bibliographicCitation | NATURE CHEMISTRY, v.5, no.1, pp 15 - 20 | - |
dc.citation.title | NATURE CHEMISTRY | - |
dc.citation.volume | 5 | - |
dc.citation.number | 1 | - |
dc.citation.startPage | 15 | - |
dc.citation.endPage | 20 | - |
dc.description.isOpenAccess | N | - |
dc.description.journalRegisteredClass | sci | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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