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用于构建吡嗪稠合双氮杂[7]螺旋烯的串联电氧化C-C和C-N偶联及芳构化反应

Tandem Electro-Oxidative C-C and C-N Coupling and Aromatization for the Construction of Pyrazine-Fused Bisaza[7]helicene.

作者信息

Zhu Qiwei, Kan Chenxia, Cao Yucai, Tang Zefeng, Xu Kang, Hang Pengjie, Li Biao, Yao Yuxin, Lei Ming, Yu Xuegong

机构信息

Department of Chemistry, Zhejiang University, Hangzhou 310027, China.

State Key Laboratory of Silicon Materials and School of Materials Science and Engineering, Zhejiang University, Hangzhou 310027, China.

出版信息

Org Lett. 2022 Oct 7;24(39):7053-7057. doi: 10.1021/acs.orglett.2c02370. Epub 2022 Aug 19.

Abstract

Repeated tandem electro-oxidative C-C and C-N coupling and aromatization were employed for the efficient construction of aza[7]helicene () as a key intermediate and the targeted pyrazine-fused bisaza[7]helicene () derivatives in 90.0-93.2% isolated yields under a controlled potential. The electrosynthetic protocol showed high selectivity and enabled rapid access to functionalized organic conjugated materials from readily available polycyclic aromatic amines. A synthetic mechanistic study along with an investigation of the photoelectrical properties and application of as a potential hole-transporting material for perovskite solar cells were performed.

摘要

通过重复串联电氧化C-C和C-N偶联及芳构化反应,在可控电位下以90.0 - 93.2%的分离产率高效构建了氮杂[7]螺旋烯()作为关键中间体以及目标吡嗪稠合双氮杂[7]螺旋烯()衍生物。该电合成方法具有高选择性,能够从易得的多环芳胺快速获得功能化有机共轭材料。开展了合成机理研究,并对其光电性能进行了研究,还考察了其作为钙钛矿太阳能电池潜在空穴传输材料的应用。

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