Caixia Jia, Lili Wang*, Yan-Na Ma* and Zheng Duan*,
{"title":"Synthesis and Electronic Properties of Arene-Fused o-Carborane","authors":"Caixia Jia, Lili Wang*, Yan-Na Ma* and Zheng Duan*, ","doi":"10.1021/acs.organomet.5c0002610.1021/acs.organomet.5c00026","DOIUrl":null,"url":null,"abstract":"<p >A transition-metal-free, base-mediated intramolecular C-arylation of <i>o</i>-carborane provides facile access to arene<i>-</i>fused <i>o</i>-carboranes. The new naphthyl-fused <i>o</i>-carborane <b>2,</b> as a fluoranthene analogue, was obtained with the reaction of 1-(8-Br-1-naphthyl)-<i>o</i>-carborane under basic conditions. This method is also applicable to the synthesis of biaryl-fused <i>o</i>-carboranes. The corresponding arene-fused <i>nido</i>-carborane was further obtained after deboronation with <i><sup>n</sup></i>Bu<sub>4</sub>NF. The fluorescence quantum efficiency of <b>5</b> has shown significant improvement compared to fluoranthene (Φ<sub>PL</sub>: 0.79 vs 0.2). In addition, the aromaticity of the <i>o</i>-carborane-annulated ring systems in these new compounds was studied and found to be enhanced compared to the corresponding rings of fluoranthene.</p>","PeriodicalId":56,"journal":{"name":"Organometallics","volume":"44 8","pages":"938–943 938–943"},"PeriodicalIF":2.5000,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organometallics","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.organomet.5c00026","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
A transition-metal-free, base-mediated intramolecular C-arylation of o-carborane provides facile access to arene-fused o-carboranes. The new naphthyl-fused o-carborane 2, as a fluoranthene analogue, was obtained with the reaction of 1-(8-Br-1-naphthyl)-o-carborane under basic conditions. This method is also applicable to the synthesis of biaryl-fused o-carboranes. The corresponding arene-fused nido-carborane was further obtained after deboronation with nBu4NF. The fluorescence quantum efficiency of 5 has shown significant improvement compared to fluoranthene (ΦPL: 0.79 vs 0.2). In addition, the aromaticity of the o-carborane-annulated ring systems in these new compounds was studied and found to be enhanced compared to the corresponding rings of fluoranthene.
期刊介绍：
Organometallics is the flagship journal of organometallic chemistry and records progress in one of the most active fields of science, bridging organic and inorganic chemistry. The journal publishes Articles, Communications, Reviews, and Tutorials (instructional overviews) that depict research on the synthesis, structure, bonding, chemical reactivity, and reaction mechanisms for a variety of applications, including catalyst design and catalytic processes; main-group, transition-metal, and lanthanide and actinide metal chemistry; synthetic aspects of polymer science and materials science; and bioorganometallic chemistry.
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