American Chemical Society
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Tandem Electro-Oxidative C–C and C–N Coupling and Aromatization for the Construction of Pyrazine-Fused Bis-aza[7]helicene

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journal contribution
posted on 2022-08-19, 15:20 authored by Qiwei Zhu, Chenxia Kan, Yucai Cao, Zefeng Tang, Kang Xu, Pengjie Hang, Biao Li, Yuxin Yao, Ming Lei, Xuegong Yu
Repeated tandem electro-oxidative C–C and C–N coupling and aromatization were employed for the efficient construction of aza[7]helicene (BA7) as a key intermediate and the targeted pyrazine-fused bis-aza[7]helicene (PBBA7) 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 PBBA7-C16 as a potential hole-transporting material for perovskite solar cells were performed.