Formation of persistent organic diradicals from N,N'-diphenyl-3,7-diazacyclooctanes.

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2018-10-29 DOI:10.1007/s00706-018-2298-4
Sara Norrehed, Christoffer Karlsson, Mark E Light, Anders Thapper, Ping Huang, Adolf Gogoll
{"title":"Formation of persistent organic diradicals from <i>N</i>,<i>N'</i>-diphenyl-3,7-diazacyclooctanes.","authors":"Sara Norrehed, Christoffer Karlsson, Mark E Light, Anders Thapper, Ping Huang, Adolf Gogoll","doi":"10.1007/s00706-018-2298-4","DOIUrl":null,"url":null,"abstract":"<p><strong>Abstract: </strong><i>N</i>,<i>N'</i>-Diphenyl-3,7-diazacyclooctane and structurally related <i>N</i>,<i>N'</i>-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C-C coupling reaction to produce dication-diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.</p><p><strong>Graphical abstract: </strong></p>","PeriodicalId":18766,"journal":{"name":"Monatshefte Fur Chemie","volume":"150 1","pages":"77-84"},"PeriodicalIF":1.7000,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6320754/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Monatshefte Fur Chemie","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s00706-018-2298-4","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2018/10/29 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

Abstract: N,N'-Diphenyl-3,7-diazacyclooctane and structurally related N,N'-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C-C coupling reaction to produce dication-diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.

Graphical abstract:

Abstract Image

Abstract Image

Abstract Image

由 N,N'-二苯基-3,7-二氮杂环辛烷形成持久性有机二卤化物。
摘要:N,N'-二苯基-3,7-二氮杂环辛烷和结构相关的 N,N'-二苯基双脒衍生物与银(I)离子发生高产的 C-C 偶联反应,生成二阳离子-二极物种,银离子具有模板和氧化剂的双重功能。生成的双(苯并咪唑)酞衍生物是一种持久性有机自由基,在溶液和固态中、室温及以上条件下以及暴露在大气中都能稳定数月。其分子结构以双层环烷为特征,通过分子内两个脱位苯并咪啶自由基段的π-二聚化而稳定。分子间的π-二聚体在固态下形成:
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Monatshefte Fur Chemie
Monatshefte Fur Chemie 化学-化学综合
CiteScore
3.70
自引率
5.60%
发文量
116
审稿时长
3.3 months
期刊介绍: "Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信