Nagalexmi Mamveedu Saji, Madeleine R. Taylor, Daniel M. Mazzucato, Paul J. Low, Li Feng Lim, Nicholas Cox, Nicholas F. Chilton, Stephen A. Moggach, Gemma F. Turner, Marcus J. Giansiracusa, Colette Boskovic, Curtis C. Ho, Stuart C. Thickett, Melissa K. Stanfield, Alex C. Bissember, Rebecca O. Fuller
{"title":"Synthesis, Structure, and Redox Properties of Nonsymmetric 6-Oxoverdazyls","authors":"Nagalexmi Mamveedu Saji, Madeleine R. Taylor, Daniel M. Mazzucato, Paul J. Low, Li Feng Lim, Nicholas Cox, Nicholas F. Chilton, Stephen A. Moggach, Gemma F. Turner, Marcus J. Giansiracusa, Colette Boskovic, Curtis C. Ho, Stuart C. Thickett, Melissa K. Stanfield, Alex C. Bissember, Rebecca O. Fuller","doi":"10.1021/acs.orglett.4c02854","DOIUrl":null,"url":null,"abstract":"Nonsymmetric 6π-electron (“oxidized”) 6-oxoverdazyls have been synthesized for the first time. After formal incorporation of a hydrogen atom, the corresponding 7π-electron neutral verdazyl radical is generated. The 7π radical can undergo a further electrochemically reversible reduction to an 8π anion. Both redox processes occur at more moderate potentials than the parent verdazyl, tuning the accessible potential windows of 6π, 7π, and 8π verdazyl species.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c02854","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Nonsymmetric 6π-electron (“oxidized”) 6-oxoverdazyls have been synthesized for the first time. After formal incorporation of a hydrogen atom, the corresponding 7π-electron neutral verdazyl radical is generated. The 7π radical can undergo a further electrochemically reversible reduction to an 8π anion. Both redox processes occur at more moderate potentials than the parent verdazyl, tuning the accessible potential windows of 6π, 7π, and 8π verdazyl species.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.