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Calix[2]azolium[2]benzimidazolone hosts for selective binding of neutral substrates in water

Author

Listed:
  • Sha Bai

    (Northwest University)

  • Lu-Wen Zhang

    (Northwest University)

  • Zi-Hang Wei

    (Northwest University)

  • Fang Wang

    (Northwest University)

  • Qing-Wen Zhu

    (Northwest University)

  • Ying-Feng Han

    (Northwest University)

Abstract

The separation and purification of chemical raw materials, particularly neutral compounds with similar physical and chemical properties, represents an ongoing challenge. In this study, we introduce a class of water-soluble macrocycle compound, calix[2]azolium[2]benzimidazolone (H), comprising two azolium and two benzimidazolone subunits. The heterocycle subunits form a hydrophobic binding pocket that enables H1 to encapsulate a series of neutral guests in water with 1:1 or 2:1 stoichiometry, including aldehydes, ketones, and nitrile compounds. The host-guest complexation in the solid state was further confirmed through X-ray crystallography. Remarkably, H1 was shown to be a nonporous adaptive crystal material to separate valeraldehyde from the mixture of valeraldehyde/2-methylbutanal/pentanol with high selectivity and recyclability in the solid states. This work not only demonstrates that azolium-based macrocycles are promising candidates for the encapsulation of organic molecules but also shows the potential application in separation science.

Suggested Citation

  • Sha Bai & Lu-Wen Zhang & Zi-Hang Wei & Fang Wang & Qing-Wen Zhu & Ying-Feng Han, 2024. "Calix[2]azolium[2]benzimidazolone hosts for selective binding of neutral substrates in water," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50980-z
    DOI: 10.1038/s41467-024-50980-z
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    References listed on IDEAS

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    1. Yuta Sawanaka & Masahiro Yamashina & Hiroyoshi Ohtsu & Shinji Toyota, 2022. "A self-complementary macrocycle by a dual interaction system," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    2. Young Chun & N Jiten Singh & In-Chul Hwang & Jung Woo Lee & Seong Uk Yu & Kwang S Kim, 2013. "Calix[n]imidazolium as a new class of positively charged homo-calix compounds," Nature Communications, Nature, vol. 4(1), pages 1-8, June.
    3. Bin Li & Lingling Liu & Yuan Wang & Kun Liu & Zhe Zheng & Shougang Sun & Yongxu Hu & Liqiang Li & Chunju Li, 2024. "Structurally diverse macrocycle co-crystals for solid-state luminescence modulation," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    4. 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.
    5. Shuo Li & Kun Liu & Xue-Chen Feng & Zhao-Xian Li & Zhi-Yuan Zhang & Bin Wang & Minjie Li & Yue-Ling Bai & Lei Cui & Chunju Li, 2022. "Synthesis and macrocyclization-induced emission enhancement of benzothiadiazole-based macrocycle," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
    6. Jian Yang & Shao-Jun Hu & Li-Xuan Cai & Li-Peng Zhou & Qing-Fu Sun, 2023. "Counteranion-mediated efficient iodine capture in a hexacationic imidazolium organic cage enabled by multiple non-covalent interactions," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
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