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Carbazole-Based Polyimide Membranes with Hydrogen-Bonding Interactions for Gas Separation

  • Yuyang Xiao
    Yuyang Xiao
    School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional and Smart Polymer Materials of Ministry of Industry and Information Technology, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    Xi’an Key Laboratory of Functional Organic Porous Materials, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    School of Chemistry and Chemical Engineering, Key Laboratory of Material Physics and Chemistry under Extraordinary Conditions of Ministry of Education, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
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  • Xingfeng Lei*
    Xingfeng Lei
    School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional and Smart Polymer Materials of Ministry of Industry and Information Technology, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    Xi’an Key Laboratory of Functional Organic Porous Materials, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    School of Chemistry and Chemical Engineering, Key Laboratory of Material Physics and Chemistry under Extraordinary Conditions of Ministry of Education, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    *Email: [email protected]
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  • Zixiang Zhang
    Zixiang Zhang
    School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional and Smart Polymer Materials of Ministry of Industry and Information Technology, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    Xi’an Key Laboratory of Functional Organic Porous Materials, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    School of Chemistry and Chemical Engineering, Key Laboratory of Material Physics and Chemistry under Extraordinary Conditions of Ministry of Education, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
  • Siyu Chen
    Siyu Chen
    School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional and Smart Polymer Materials of Ministry of Industry and Information Technology, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    Xi’an Key Laboratory of Functional Organic Porous Materials, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    School of Chemistry and Chemical Engineering, Key Laboratory of Material Physics and Chemistry under Extraordinary Conditions of Ministry of Education, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    More by Siyu Chen
  • Guo Xiong
    Guo Xiong
    School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional and Smart Polymer Materials of Ministry of Industry and Information Technology, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    Xi’an Key Laboratory of Functional Organic Porous Materials, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    School of Chemistry and Chemical Engineering, Key Laboratory of Material Physics and Chemistry under Extraordinary Conditions of Ministry of Education, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    More by Guo Xiong
  • Xiaohua Ma
    Xiaohua Ma
    State Key Laboratory of Separation Membranes and Membrane Processes, National Center for International Joint Research on Membrane Science and Technology, Tiangong University, Tianjin 300387, P. R. China
    More by Xiaohua Ma
  • , and 
  • Qiuyu Zhang*
    Qiuyu Zhang
    School of Chemistry and Chemical Engineering, Key Laboratory of Special Functional and Smart Polymer Materials of Ministry of Industry and Information Technology, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    Xi’an Key Laboratory of Functional Organic Porous Materials, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    School of Chemistry and Chemical Engineering, Key Laboratory of Material Physics and Chemistry under Extraordinary Conditions of Ministry of Education, Northwestern Polytechnical University, Xi’an, Shaanxi 710072, P. R. China
    *Email: [email protected]. Tel/Fax: +86-029-88431653.
    More by Qiuyu Zhang
Cite this: Macromolecules 2024, XXXX, XXX, XXX-XXX
Publication Date (Web):June 8, 2024
https://doi.org/10.1021/acs.macromol.4c00255
© 2024 American Chemical Society

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    Abstract

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    Cross-linked polymers for gas separation have significant advantages in increasing gas selectivity and separation stability. However, the cross-linking strategies unavoidably form permanent interchain covalent bonds and alter the polymer packing state, which largely decrease polymer solubility, static toughness, and reprocessability. Herein, a secondary-amine-containing diamine (HCBDA) derived from carbazole is synthesized and polymerized with 6FDA to furnish a gas-permeable polyimide (HCB-PI) with a pseudo-cross-linked hydrogen-bonding network and a strengthened charge-transfer complex (CTC) effect. Compared with the hydrogen-bonding free sample (CB-PI), HCB-PI displays a more homogeneous micropore distribution and denser chain packing, as is proven by positron annihilation lifetime spectroscopy, which results in enhanced selectivity for O2/N2 and CO2/CH4 gas pairs and antiplasticization property. Owing to the stronger interaction between the HCB-PI skeleton and molecular oxygen and thus the competitive adsorption mechanism, HCB-PI exhibits more enhanced O2/N2 selectivity in mixed-gas measurements (7.54) than in pure-gas measurements (6.58), with the overall separation property approaching the 2008 Robeson upper bound. Additionally, HCB-PI is heat-resistant and mechanically robust, exhibiting static toughness up to 108 MJ·m–3. Our designing concept for HCB-PI has been demonstrated to be efficacious for oxygen enrichment from air.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.macromol.4c00255.

    • Experimental section, FT-IR, NMR, HS-MS, fluorescence, UV–vis and VT-IR spectra, specific data for gas separation properties, DMA, TGA, GPC and WAXD curves, and tensile stress–strain curves (PDF)

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