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Synthesis of three-dimensional covalent organic frameworks through a symmetry reduction strategy

Nature Chemistry volume 17, pages 571–581 (2025)Cite this article

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Abstract

Three-dimensional (3D) covalent organic frameworks (COFs) hold significant promise for a variety of applications. However, conventional design approaches using regular building blocks limit the structural diversity of 3D COFs. Here we design and synthesize two 3D COFs, designated as JUC-644 and JUC-645, through a methodology that relies on using eight-connected building blocks with reduced symmetry. Their structures are solved using continuous rotation electron diffraction and high-resolution transmission electron microscopy, which reveal a unique linkage with a double chain structure, a rare phenomenon in COFs. We deconstruct these structures into [4 + 3(+ 2)]-c nets, which leads to six different topologies. Furthermore, JUC-644 demonstrates high adsorption capacity for C3H8 and n-C4H10 (11.28 and 10.45 mmol g−1 at 298 K and 1 bar, respectively), surpassing most known porous materials, with notable selectivity for C3H8/C2H6 and n-C4H10/C2H6. This approach opens avenues for designing intricate architectures and shows the potential of COFs in C2H6 recovery from natural gas liquids.

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Fig. 1: Schematic illustration of 3D COFs based on different strategies.
Fig. 2: Schematic representation for the synthesis of JUC-644 and JUC-645.
Fig. 3: Structural characterization of JUC-644 and JUC-645.
Fig. 4: Structural analysis of COFs.
Fig. 5: Schematic illustration of the discovery of topologies.
Fig. 6: Porosity analysis and adsorption and separation towards various light hydrocarbon molecules of JUC-644 and JUC-645.

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Data availability

Crystallographic data for the structures reported in this article have been deposited at the Cambridge Crystallographic Data Centre, under deposition numbers CCDC 2296805 (JUC-644) and 2353775 (JUC-645). Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/. The authors declare that the data supporting the findings of this study are available within the article and its Supplementary Information, or from the corresponding authors on reasonable request. Source data are provided with this paper.

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Acknowledgements

Q.F., J. Sun and H.L. acknowledge support from the National Key R&D Program of China (2022YFB3704900 and 2021YFF0500504), National Natural Science Foundation of China (22025504, 21621001, 22105082, U21A20285, 22125102, 22475081 and 21527803), Shanghai synchrotron radiation facility (bl14B), the SINOPEC Research Institute of Petroleum Processing, ‘111’ project (BP0719036 and B17020), China Postdoctoral Science Foundation (2020TQ0118 and 2020M681034), Ministry of Science and Technology of the People’s Republic of China (grant no. 2020YFA0210700) and the programme for JLU Science and Technology Innovative Research Team. V.V., Q.F. and S.Q. acknowledge the collaboration in the Sino-French International Research Network ‘Zeolites’.

Author information

Author notes

  1. These authors contributed equally: Jianhong Chang, Zeyue Zhang, Haorui Zheng.

Authors and Affiliations

  1. State Key Laboratory of Inorganic Synthesis and Preparative Chemistry, Jilin University, Changchun, People’s Republic of China

    Jianhong Chang, Haorui Zheng, Hui Li, Jinquan Suo, Fenqian Chen, Zitao Wang, Shilun Qiu & Qianrong Fang

  2. College of Chemistry and Molecular Engineering, Beijing National Laboratory for Molecular Sciences, Peking University, Beijing, People’s Republic of China

    Zeyue Zhang, Shipeng Zhang & Junliang Sun

  3. Department of Chemical and Biomolecular Engineering, National University of Singapore, Singapore, Singapore

    Chunqing Ji

  4. Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, People’s Republic of China

    Valentin Valtchev

  5. Laboratoire Catalyse et Spectrochimie, Normandie Université, ENSICAEN, UNICAEN, CNRS, Caen, France

    Valentin Valtchev

Authors
  1. Jianhong Chang
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Contributions

Q.F., H.L., J. Sun, V.V. and S.Q. were responsible for the overall project design, direction and supervision. J.C. and H.Z. conducted the synthesis and characterization of all samples. Z.Z., S.Z. and J. Sun collected and analysed the cRED data and topology structure. J.C., Z.Z., H.Z. and H.L. finalized the PXRD refinement and structure analyses. J.C., H.Z. and H.L. conducted the alkane sorption tests and breakthrough experiments. J. Suo and F.C. performed DFT calculations and assisted with the thermogravimetric analysis and FT-IR tests. C.J. assisted with the calculation of Qst and the ideal adsorbed solution theory for alkane sorption. Z.W. captured HRTEM images. All authors contributed to the discussion of results and paper writing.

Corresponding authors

Correspondence to Hui Li, Junliang Sun or Qianrong Fang.

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Extended data

Extended Data Fig. 1 Breakthrough experiments for JUC-644.

Column breakthrough curves for C2H6/C3H8 (a) and C2H6/n-C4H10 (b) mixture (50:50, v/v, Tfr: 2.0 mL min-1) at 298 K. (c) Column breakthrough curves for dry and moist C2H6/C3H8/n-C4H10 mixture (46:34:20, v/v/v, Tfr: 5.0 mL min-1) at 298 K. (d) Cycling breakthrough test of C2H6/C3H8/n-C4H10 mixture (46:34:20, v/v/v, Tfr: 5.0 mL/min) at 298 K.

Source data

Supplementary information

Supplementary Information (download PDF )

Supplementary Figs. 1–81 and Tables 1–21.

Supplementary Video 1 (download GIF )

Animation showing a simulation of the trajectory changes of C2H6 within JUC-644. For details see Supplementary Fig. 70.

Supplementary Video 2 (download GIF )

Animation showing a simulation of the trajectory changes of C3H8 within JUC-644. For details see Supplementary Fig. 70.

Supplementary Video 3 (download GIF )

Animation showing a simulation of the trajectory changes of C4H10 within JUC-644. For details see Supplementary Fig. 70.

Supplementary Data 1

Crystallographic data for JUC-644 (CCDC 2296805).

Supplementary Data 2

Crystallographic data for JUC-645 (CCDC 2353775).

Supplementary Data 3 (download XLSX )

The atomic coordinates of the optimized computational models, Supplementary Fig. 3.

Source data

Source Data Fig. 3 (download XLSX )

Unprocessed PXRD source data.

Source Data Fig. 6 (download ZIP )

Unprocessed source data for N2 adsorption–desorption isotherms at 77 K and C2H6, C3Hs and n-C4H10 adsorption isotherms at 298 K.

Source Data Extended Data Fig. 1 (download XLSX )

Unprocessed source data for column breakthrough curves of C2H6/C3Hs and C2H6/n-C4H10 mixtures at 298 K, column breakthrough curves for dry and humid C2H6/C3Hs/n-C4H10 mixtures, and cycle breakthrough tests for C2H6/C3Hs/n-C4H10 mixtures.

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Chang, J., Zhang, Z., Zheng, H. et al. Synthesis of three-dimensional covalent organic frameworks through a symmetry reduction strategy. Nat. Chem. 17, 571–581 (2025). https://doi.org/10.1038/s41557-024-01715-6

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