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<p>Organic nanotubes have garnered significant attention over recent decades due to their potential applications across various fields. Despite this, the synthesis of stable organic nanotubes with precise stereochemical control remains challenging. While dynamic covalent chemistry has proven to be a powerful tool for efficiently constructing stable organic nanotubes, precise stereochemical control of low-symmetry chiral nanotubes is still an area requiring further exploration. Here we report the synthesis of a low-symmetry chiral organic nanotube through dynamic covalent self-assembly of a rim-differentiated pentathiol-functionalized pillar[5]arene (<b>p5-SH</b>). Dimerization of this highly symmetric building block generates a covalently linked low-symmetry organic nanotube ([<b>p5-S</b>]<sub><b>2</b></sub>). A pair of enantiomers, <Emphasis Type="BoldItalic">P′M</Emphasis>-[<b>p5-S</b>]<sub><b>2</b></sub> and <Emphasis Type="BoldItalic">M′P</Emphasis>-[<b>p5-S</b>]<sub><b>2</b></sub>, was separated and characterized. The assembly and disassembly of [<b>p5-S</b>]<sub><b>2</b></sub> are redox-regulated, with disulfide bonds functioning as molecular switches. Furthermore, the synergistic effects of dual pillar[5]arene cavities in [<b>p5-S</b>]<sub><b>2</b></sub> create a deep cavity with a rigid asymmetric architecture. This structure significantly enhances the nanotube’s ability to recognize linear alkyl chains in solution, making it a promising candidate for various applications in materials science and nanotechnology.</p>

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Dynamic covalent assembly of low-symmetry chiral organic nanotubes via disulfide-bridged pillar[5]arene dimerization

  • 期刊论文

  • 发表日期：

    2025年11月6日

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  • Ping Li,
  • Kai Lan,
  • Xiaobo Zhang,
  • Hanchi Zhong,
  • Chuyang Cheng

摘要

Organic nanotubes have garnered significant attention over recent decades due to their potential applications across various fields. Despite this, the synthesis of stable organic nanotubes with precise stereochemical control remains challenging. While dynamic covalent chemistry has proven to be a powerful tool for efficiently constructing stable organic nanotubes, precise stereochemical control of low-symmetry chiral nanotubes is still an area requiring further exploration. Here we report the synthesis of a low-symmetry chiral organic nanotube through dynamic covalent self-assembly of a rim-differentiated pentathiol-functionalized pillar[5]arene (p5-SH). Dimerization of this highly symmetric building block generates a covalently linked low-symmetry organic nanotube ([p5-S]2). A pair of enantiomers, P′M-[p5-S]2 and M′P-[p5-S]2, was separated and characterized. The assembly and disassembly of [p5-S]2 are redox-regulated, with disulfide bonds functioning as molecular switches. Furthermore, the synergistic effects of dual pillar[5]arene cavities in [p5-S]2 create a deep cavity with a rigid asymmetric architecture. This structure significantly enhances the nanotube’s ability to recognize linear alkyl chains in solution, making it a promising candidate for various applications in materials science and nanotechnology.