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<p>The precise separation of enantiomers is essential for developing effective chiral drugs, yet conventional membranes are constrained by the ubiquitous selectivity-permeability trade-off and low flux, limiting scalable production of single-enantiomer drugs. Herein, we present a cascade reaction strategy integrating Sonogashira-Hagihara coupling and Friedel-Crafts alkylation to fabricate porous conjugated microporous polymer membranes (CCMP-M<sub>P1−4</sub>/SiO<sub>2</sub>). This approach enhances specific surface area by 400-fold compared to the product from the Sonogashira-Hagihara coupling reaction alone, creating interconnected porous networks that facilitate mass transport. This hypothesis was confirmed by pore-size gradient experiments, which revealed a critical size-matching effect: matched molecular dimensions enable high-speed mass transfer with 97% enantioselectivity, while mismatch reduces selectivity to 9%, as visualized in a separation performance matrix across four chiral molecules. Precise chiral recognition is programmable via absolute configuration control of chiral monomers, with the mechanism of “preferential adsorption–interfacial enrichment–promoted diffusion” confirmed by static adsorption and density functional theory calculations. This strategy achieves breakthrough performance: Naproxen flux reaches 37 mmol m<sup>−2</sup> h<sup>−1</sup>, surpassing literature values, and enables membrane-based separation of Raceanisodamine (89% selectivity of 6S, 2′<i>S</i> and 6<i>R</i>, 2′<i>R</i>-isomer after cascade enrichment) for the first time. This work provides a new paradigm for designing high-performance chiral separation membranes, facilitating scalable and sustainable production of single-enantiomer drugs.</p>

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Cascade-controlled porous composite membranes: pore-supporting synergy enabling high-flux enantioseparation of amino acids and pharmaceuticals

  • 期刊论文

  • 发表日期：

    2026年3月11日

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  • Yu Zang,
  • Rui Hou,
  • Bohua Wei,
  • Yuting Liu,
  • Jianjun Wang,
  • Jiao Liu,
  • Liang Xu,
  • Wei Zhang

摘要

The precise separation of enantiomers is essential for developing effective chiral drugs, yet conventional membranes are constrained by the ubiquitous selectivity-permeability trade-off and low flux, limiting scalable production of single-enantiomer drugs. Herein, we present a cascade reaction strategy integrating Sonogashira-Hagihara coupling and Friedel-Crafts alkylation to fabricate porous conjugated microporous polymer membranes (CCMP-MP1−4/SiO2). This approach enhances specific surface area by 400-fold compared to the product from the Sonogashira-Hagihara coupling reaction alone, creating interconnected porous networks that facilitate mass transport. This hypothesis was confirmed by pore-size gradient experiments, which revealed a critical size-matching effect: matched molecular dimensions enable high-speed mass transfer with 97% enantioselectivity, while mismatch reduces selectivity to 9%, as visualized in a separation performance matrix across four chiral molecules. Precise chiral recognition is programmable via absolute configuration control of chiral monomers, with the mechanism of “preferential adsorption–interfacial enrichment–promoted diffusion” confirmed by static adsorption and density functional theory calculations. This strategy achieves breakthrough performance: Naproxen flux reaches 37 mmol m−2 h−1, surpassing literature values, and enables membrane-based separation of Raceanisodamine (89% selectivity of 6S, 2′S and 6R, 2′R-isomer after cascade enrichment) for the first time. This work provides a new paradigm for designing high-performance chiral separation membranes, facilitating scalable and sustainable production of single-enantiomer drugs.