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Facile access to C-N bonds via unexpected side reactions of Knoevenagel condensation and their application in high-efficiency organic solar cells

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Abstract

The construction of C-N bonds is of great importance in the fields of biology, medicine, chemistry and materials science. Here, the replacement of organic base from pyridine to piperidine in the Knoevenagel condensation process unexpectedly yields a series of novel organic molecules containing C-N bonds. Interestingly, the synthesis method does not require any external transition-metals catalysis, and photo-/electro-catalysis. Additionally, when the new compound 1b is added as a third component to a well-known binary system of PM6:Y6, the efficiency of the organic solar cell is significantly improved, resulting in an outstanding efficiency of 18.0%, which is one of the highest values reported to date for PM6:Y6-based ternary organic solar cells.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (U21A20331), the National Science Fund for Distinguished Young Scholars (21925506), and the Zhejiang Provincial Natural Science Foundation of China (LQ22E030013). We thank Prof. Bijin Li (School of Pharmaceutical Sciences, Chongqing University) and Prof. Tao Xiong (Department of Chemistry, Northeast Normal University) for the friendly discussion on the mechanism of C-N bond formation.

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Authors and Affiliations

  1. Zhejiang Engineering Research Center for Energy Optoelectronic Materials and Devices, Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo, 315201, China

    Daobin Yang, Shuncheng Yang, Hongqian Wang, Lin Xie, Pengyu Yan & Ziyi Ge

  2. School of Materials Science and Chemical Engineering, Ningbo University, Ningbo, 315211, China

    Shuncheng Yang & Hongqian Wang

  3. Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing, 100049, China

    Daobin Yang & Ziyi Ge

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  1. Daobin Yang
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  2. Shuncheng Yang
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  4. Lin Xie
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  5. Pengyu Yan
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Correspondence to Daobin Yang or Ziyi Ge.

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Supporting information The supporting information is available online at https://chem.scichina.com and https://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Facile access to C-N bonds via unexpected side reactions of Knoevenagel condensation and their high efficiency organic solar cells

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Yang, D., Yang, S., Wang, H. et al. Facile access to C-N bonds via unexpected side reactions of Knoevenagel condensation and their application in high-efficiency organic solar cells. Sci. China Chem. 67, 323–329 (2024). https://doi.org/10.1007/s11426-023-1752-3

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  • DOI: https://doi.org/10.1007/s11426-023-1752-3

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