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Grinding-induced supramolecular charge-transfer assemblies with switchable vapochromism toward haloalkane isomers

Author

Listed:
  • Jia-Rui Wu

    (Jilin University
    Jilin University)

  • Gengxin Wu

    (Jilin University)

  • Dongxia Li

    (Jilin University)

  • Meng-Hao Li

    (Jilin University)

  • Yan Wang

    (Jilin University)

  • Ying-Wei Yang

    (Jilin University)

Abstract

Synthetic macrocycles have proved to be of great application value in functional charge-transfer systems in the solid state in recent years. Here we show a switchable on-off type vapochromic system toward 1-/2-bromoalkane isomers by constructing solid-state charge-transfer complexes between electron-rich perethylated pillar[5]arene and electron-deficient aromatic acceptors including 4-nitrobenzonitrile and 1,4-dinitrobenzene. These charge-transfer complexes with different colors show opposite color changes upon exposure to the vapors of 1-bromoalkanes (fading) and 2-bromoalkanes (deepening). Single-crystal structures incorporating X-ray powder diffraction and spectral analyses demonstrate that this on-off type vapochromic behavior is mainly attributed to the destruction (off) and reconstruction (on) of the charge-transfer interactions between perethylated pillar[5]arene and the acceptors, for which the competitive host-guest binding of 1-bromoalkanes and the solid-state structural transformation triggered by 2-bromoalkanes are respectively responsible. This work provides a simple colorimetric method for distinguishing positional isomers with similar physical and chemical properties.

Suggested Citation

  • Jia-Rui Wu & Gengxin Wu & Dongxia Li & Meng-Hao Li & Yan Wang & Ying-Wei Yang, 2023. "Grinding-induced supramolecular charge-transfer assemblies with switchable vapochromism toward haloalkane isomers," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-41713-9
    DOI: 10.1038/s41467-023-41713-9
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    References listed on IDEAS

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    1. Xiao-Ni Han & Ying Han & Chuan-Feng Chen, 2021. "Supramolecular tessellations by the exo-wall interactions of pagoda[4]arene," Nature Communications, Nature, vol. 12(1), pages 1-12, December.
    2. Dongdong Sun & Yong Wu & Xie Han & Simin Liu, 2023. "The host–guest inclusion driven by host-stabilized charge transfer for construction of sequentially red-shifted mechanochromic system," Nature Communications, Nature, vol. 14(1), pages 1-12, December.
    3. Alok S. Tayi & Alexander K. Shveyd & Andrew C.-H. Sue & Jodi M. Szarko & Brian S. Rolczynski & Dennis Cao & T. Jackson Kennedy & Amy A. Sarjeant & Charlotte L. Stern & Walter F. Paxton & Wei Wu & Sanj, 2012. "Room-temperature ferroelectricity in supramolecular networks of charge-transfer complexes," Nature, Nature, vol. 488(7412), pages 485-489, August.
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    1. Jingyu Chen & Wenjie Zhang & Wenzhi Yang & Fengcheng Xi & Hongyi He & Minghao Liang & Qian Dong & Jiawang Hou & Mengbin Wang & Guocan Yu & Jiong Zhou, 2024. "Separation of benzene and toluene associated with vapochromic behaviors by hybrid[4]arene-based co-crystals," Nature Communications, Nature, vol. 15(1), pages 1-13, December.

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