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

中文翻译：

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由 N,N'-二苯基-3,7-二氮杂环辛烷形成持久性有机双自由基。

 抽象的

N , N'-二苯基-3,7-二氮杂环辛烷和结构相关的N , N'-二苯基双吡啶衍生物与银 (I) 离子进行高产率 C-C 偶联反应，产生双自由基物质，其中银离子具有作为模板和氧化剂的双重功能。所得双(联苯胺基)芬衍生物是持久性有机自由基，在室温及以上温度以及暴露在大气中时，无论在溶液中还是在固态中均可稳定几个月。该分子结构具有双层环烷基序，通过两个离域联苯胺自由基片段的分子内 π-二聚化来稳定。分子间π-二聚体在固态下形成。

 图文摘要