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Addition of alkynes and osmium carbynes towards functionalized dπ–pπ conjugated systems

Author

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  • Shiyan Chen

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University)

  • Longzhu Liu

    (Southern University of Science and Technology)

  • Xiang Gao

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University)

  • Yuhui Hua

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University)

  • Lixia Peng

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University)

  • Ying Zhang

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University)

  • Liulin Yang

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University)

  • Yuanzhi Tan

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University)

  • Feng He

    (Southern University of Science and Technology)

  • Haiping Xia

    (State Key Laboratory of Physical Chemistry of Solid Surfaces and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), College of Chemistry and Chemical Engineering, Xiamen University
    Southern University of Science and Technology)

Abstract

The metal-carbon triple bonds and carbon-carbon triple bonds are both highly unsaturated bonds. As a result, their reactions tend to afford cycloaddition intermediates or products. Herein, we report a reaction of M≡C and C≡C bonds that affords acyclic addition products. These newly discovered reactions are highly efficient, regio- and stereospecific, with good functional group tolerance, and are robust under air at room temperature. The isotope labeling NMR experiments and theoretical calculations reveal the reaction mechanism. Employing these reactions, functionalized dπ-pπ conjugated systems can be easily constructed and modified. The resulting dπ-pπ conjugated systems were found to be good electron transport layer materials in organic solar cells, with power conversion efficiency up to 16.28% based on the PM6: Y6 non-fullerene system. This work provides a facile, efficient methodology for the preparation of dπ-pπ conjugated systems for use in functional materials.

Suggested Citation

  • Shiyan Chen & Longzhu Liu & Xiang Gao & Yuhui Hua & Lixia Peng & Ying Zhang & Liulin Yang & Yuanzhi Tan & Feng He & Haiping Xia, 2020. "Addition of alkynes and osmium carbynes towards functionalized dπ–pπ conjugated systems," Nature Communications, Nature, vol. 11(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18498-2
    DOI: 10.1038/s41467-020-18498-2
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    Cited by:

    1. Xue Lai, & Shiyan Chen, & Xiaoyu Gu, & Hanjian Lai, & Yunpeng Wang, & Yulin Zhu, & Hui Wang, & Jianfei Qu, & Aung Ko Ko Kyaw & Haiping Xia & Feng He, 2023. "Phenanthroline-carbolong interface suppress chemical interactions with active layer enabling long-time stable organic solar cells," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    2. Binbin Xu & Wei Mao & Zhengyu Lu & Yuanting Cai & Dafa Chen & Haiping Xia, 2024. "Syntheses and reactivities of strained fused-ring metallaaromatics containing planar eleven-carbon chains," Nature Communications, Nature, vol. 15(1), pages 1-8, December.

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