4.8 Article

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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ORGANIC LETTERS
卷 24, 期 39, 页码 7053-7057

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02370

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资金

  1. National Natural Science Foundation of China [21975219, 62025403, 61721005]
  2. Shanghai Research Institute of Chemical Industry Co., Ltd. [SKL-LCTP-201806]
  3. Fundamental Research Funds for the Central Universities [226-2022-00200]

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A tandem electro-oxidative reaction was used to efficiently construct a key intermediate and derivatives of aza[7]helicene, demonstrating high selectivity and rapid synthesis of functionalized organic conjugated materials. The synthesized compounds were further studied for their photoelectrical properties and potential application in perovskite solar cells.
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.

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