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Facile transformation of imine covalent organic frameworks into ultrastable crystalline porous aromatic frameworks

Author

Listed:
  • Xinle Li

    (Lawrence Berkeley National Laboratory)

  • Changlin Zhang

    (Lawrence Berkeley National Laboratory)

  • Songliang Cai

    (South China Normal University)

  • Xiaohe Lei

    (Lawrence Berkeley National Laboratory
    Zhejiang University)

  • Virginia Altoe

    (Lawrence Berkeley National Laboratory)

  • Fang Hong

    (Lawrence Berkeley National Laboratory)

  • Jeffrey J. Urban

    (Lawrence Berkeley National Laboratory)

  • Jim Ciston

    (Lawrence Berkeley National Laboratory)

  • Emory M. Chan

    (Lawrence Berkeley National Laboratory)

  • Yi Liu

    (Lawrence Berkeley National Laboratory)

Abstract

The growing interest in two-dimensional imine-based covalent organic frameworks (COFs) is inspired by their crystalline porous structures and the potential for extensive π-electron delocalization. The intrinsic reversibility and strong polarization of imine linkages, however, leads to insufficient chemical stability and optoelectronic properties. Developing COFs with improved robustness and π-delocalization is highly desirable but remains an unsettled challenge. Here we report a facile strategy that transforms imine-linked COFs into ultrastable porous aromatic frameworks by kinetically fixing the reversible imine linkage via an aza-Diels-Alder cycloaddition reaction. The as-formed, quinoline-linked COFs not only retain crystallinity and porosity, but also display dramatically enhanced chemical stability over their imine-based COF precursors, rendering them among the most robust COFs up-to-date that can withstand strong acidic, basic and redox environment. Owing to the chemical diversity of the cycloaddition reaction and structural tunability of COFs, the pores of COFs can be readily engineered to realize pre-designed surface functionality.

Suggested Citation

  • Xinle Li & Changlin Zhang & Songliang Cai & Xiaohe Lei & Virginia Altoe & Fang Hong & Jeffrey J. Urban & Jim Ciston & Emory M. Chan & Yi Liu, 2018. "Facile transformation of imine covalent organic frameworks into ultrastable crystalline porous aromatic frameworks," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-05462-4
    DOI: 10.1038/s41467-018-05462-4
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    Cited by:

    1. Yongliang Yang & Ling Yu & Tiancheng Chu & Hongyun Niu & Jun Wang & Yaqi Cai, 2022. "Constructing chemical stable 4-carboxyl-quinoline linked covalent organic frameworks via Doebner reaction for nanofiltration," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Maria-Anna Gatou & Panagiota Bika & Thomas Stergiopoulos & Panagiotis Dallas & Evangelia A. Pavlatou, 2021. "Recent Advances in Covalent Organic Frameworks for Heavy Metal Removal Applications," Energies, MDPI, vol. 14(11), pages 1-26, May.
    3. Fuyang Liu & Peng Zhou & Yanghui Hou & Hao Tan & Yin Liang & Jialiang Liang & Qing Zhang & Shaojun Guo & Meiping Tong & Jinren Ni, 2023. "Covalent organic frameworks for direct photosynthesis of hydrogen peroxide from water, air and sunlight," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    4. Yunyang Qian & Yulan Han & Xiyuan Zhang & Ge Yang & Guozhen Zhang & Hai-Long Jiang, 2023. "Computation-based regulation of excitonic effects in donor-acceptor covalent organic frameworks for enhanced photocatalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    5. Shu-Yan Jiang & Zhi-Bei Zhou & Shi-Xian Gan & Ya Lu & Chao Liu & Qiao-Yan Qi & Jin Yao & Xin Zhao, 2024. "Creating amphiphilic porosity in two-dimensional covalent organic frameworks via steric-hindrance-mediated precision hydrophilic-hydrophobic microphase separation," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    6. Jia-Rui Wang & Kepeng Song & Tian-Xiang Luan & Ke Cheng & Qiurong Wang & Yue Wang & William W. Yu & Pei-Zhou Li & Yanli Zhao, 2024. "Robust links in photoactive covalent organic frameworks enable effective photocatalytic reactions under harsh conditions," Nature Communications, Nature, vol. 15(1), pages 1-17, December.
    7. Weijun Weng & Jia Guo, 2022. "The effect of enantioselective chiral covalent organic frameworks and cysteine sacrificial donors on photocatalytic hydrogen evolution," Nature Communications, Nature, vol. 13(1), pages 1-11, December.

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