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Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking

Author

Listed:
  • Minlong Wang

    (China Agricultural University)

  • Jiaman Hou

    (China Agricultural University)

  • Hainam Do

    (University of Nottingham Ningbo China)

  • Chao Wang

    (China Agricultural University)

  • Xiaohe Zhang

    (China Agricultural University)

  • Ying Du

    (China Agricultural University)

  • Qixin Dong

    (China Agricultural University)

  • Lijun Wang

    (China Agricultural University)

  • Ke Ni

    (China Agricultural University)

  • Fazheng Ren

    (China Agricultural University)

  • Jie An

    (China Agricultural University)

Abstract

SuFEx click chemistry demonstrates remarkable molecular assembly capabilities. However, the effective utilization of alkyl sulfonyl fluoride hubs in SuFEx chemistry, particularly in reactions with alcohols and primary amines, presents considerable challenges. This study pioneers an intramolecular chalcogen bonding activated SuFEx (S-SuFEx) click chemistry employing alkyl sulfonyl fluorides with γ-S as the activating group. The ChB-activated alkyl sulfonyl fluorides can react smoothly with phenols, alcohols, and amines, exhibiting enhanced reactivity compared to SO2F2. Excellent yields have been achieved with all 75 tested substrates. Pioneering the application of S-SuFEx chemistry, we highlight its immense potential in organic-inorganic linking, considering the critical role of interfacial covalent bonding in material fabrication. The S-SuFEx hub 1c, incorporating a trialkoxy silane group has been specifically designed and synthesized for organic-inorganic linking. In a simple step, 1c efficiently anchors various organic compounds onto surfaces of inorganic materials, forming functionalized surfaces with properties such as antibacterial activity, hydrophobicity, and fluorescence.

Suggested Citation

  • Minlong Wang & Jiaman Hou & Hainam Do & Chao Wang & Xiaohe Zhang & Ying Du & Qixin Dong & Lijun Wang & Ke Ni & Fazheng Ren & Jie An, 2024. "Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50922-9
    DOI: 10.1038/s41467-024-50922-9
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    References listed on IDEAS

    as
    1. Jianjian Liu & Mali Zhou & Rui Deng & Pengcheng Zheng & Yonggui Robin Chi, 2022. "Chalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    2. Genyi Meng & Taijie Guo & Tiancheng Ma & Jiong Zhang & Yucheng Shen & Karl Barry Sharpless & Jiajia Dong, 2019. "Modular click chemistry libraries for functional screens using a diazotizing reagent," Nature, Nature, vol. 574(7776), pages 86-89, October.
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