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Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens

Author

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  • Xun-Shen Liu

    (East China Normal University
    East China Normal University)

  • Zhiqiong Tang

    (East China Normal University)

  • Zhiming Li

    (Fudan University)

  • Mingjia Li

    (East China Normal University)

  • Lin Xu

    (East China Normal University)

  • Lu Liu

    (East China Normal University
    East China Normal University)

Abstract

Tetraarylethylenes exhibit intriguing photophysical properties and sulfur atom frequently play a vital role in organic photoelectric materials and biologically active compounds. Tetrasubstituted vinyl sulfides, which include both sulfur atom and tetrasubstituted alkenes motifs, might be a suitable skeleton for the discovery of the new material molecules and drug with unique functions and properties. However, how to modular synthesis these kinds of compounds is still challenging. Herein, a chemo- and stereo-selective Rh(II)-catalyzed [1,4]-acyl rearrangements of α-diazo carbonyl compounds and thioesters has been developed, providing a modular strategy to a library of 63 tetrasubstituted vinyl sulfides. In this transformation, the yield is up to 95% and the turnover number is up to 3650. The mechanism of this reaction is investigated by combining experiments and density functional theory calculation. Moreover, the “aggregation-induced emission” effect of tetrasubstituted vinyl sulfides were also investigated, which might useful in functional material, biological imaging and chemicalnsing via structural modification.

Suggested Citation

  • Xun-Shen Liu & Zhiqiong Tang & Zhiming Li & Mingjia Li & Lin Xu & Lu Liu, 2021. "Modular and stereoselective synthesis of tetrasubstituted vinyl sulfides leading to a library of AIEgens," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-27167-x
    DOI: 10.1038/s41467-021-27167-x
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