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Conjugated organic framework with three-dimensionally ordered stable structure and delocalized π clouds

Author

Listed:
  • Jia Guo

    (Institute for Molecular Science, National Institutes of Natural Sciences
    State Key Laboratory of Molecular Engineering of Polymers, Fudan University)

  • Yanhong Xu

    (Institute for Molecular Science, National Institutes of Natural Sciences)

  • Shangbin Jin

    (Institute for Molecular Science, National Institutes of Natural Sciences)

  • Long Chen

    (Institute for Molecular Science, National Institutes of Natural Sciences
    Present address: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany)

  • Toshihiko Kaji

    (Institute for Molecular Science, National Institutes of Natural Sciences)

  • Yoshihito Honsho

    (Graduate School of Engineering, Osaka University)

  • Matthew A. Addicoat

    (Graduate School of Science, Nagoya University)

  • Jangbae Kim

    (Center for Time-Resolved Diffraction, KAIST)

  • Akinori Saeki

    (Graduate School of Engineering, Osaka University)

  • Hyotcherl Ihee

    (Center for Time-Resolved Diffraction, KAIST
    Center for Nanomaterials and Chemical Reactions, Institute for Basic Science)

  • Shu Seki

    (Graduate School of Engineering, Osaka University)

  • Stephan Irle

    (Graduate School of Science, Nagoya University)

  • Masahiro Hiramoto

    (Institute for Molecular Science, National Institutes of Natural Sciences)

  • Jia Gao

    (Institute for Molecular Science, National Institutes of Natural Sciences)

  • Donglin Jiang

    (Institute for Molecular Science, National Institutes of Natural Sciences)

Abstract

Covalent organic frameworks are a class of crystalline organic porous materials that can utilize π–π-stacking interactions as a driving force for the crystallization of polygonal sheets to form layered frameworks and ordered pores. However, typical examples are chemically unstable and lack intrasheet π-conjugation, thereby significantly limiting their applications. Here we report a chemically stable, electronically conjugated organic framework with topologically designed wire frameworks and open nanochannels, in which the π conjugation-spans the two-dimensional sheets. Our framework permits inborn periodic ordering of conjugated chains in all three dimensions and exhibits a striking combination of properties: chemical stability, extended π-delocalization, ability to host guest molecules and hole mobility. We show that the π-conjugated organic framework is useful for high on-off ratio photoswitches and photovoltaic cells. Therefore, this strategy may constitute a step towards realizing ordered semiconducting porous materials for innovations based on two-dimensionally extended π systems.

Suggested Citation

  • Jia Guo & Yanhong Xu & Shangbin Jin & Long Chen & Toshihiko Kaji & Yoshihito Honsho & Matthew A. Addicoat & Jangbae Kim & Akinori Saeki & Hyotcherl Ihee & Shu Seki & Stephan Irle & Masahiro Hiramoto &, 2013. "Conjugated organic framework with three-dimensionally ordered stable structure and delocalized π clouds," Nature Communications, Nature, vol. 4(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:4:y:2013:i:1:d:10.1038_ncomms3736
    DOI: 10.1038/ncomms3736
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    Cited by:

    1. Shengcong Shang & Changsheng Du & Youxing Liu & Minghui Liu & Xinyu Wang & Wenqiang Gao & Ye Zou & Jichen Dong & Yunqi Liu & Jianyi Chen, 2022. "A one-dimensional conductive metal-organic framework with extended π-d conjugated nanoribbon layers," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Jianyu Zhang & Yujie Tu & Hanchen Shen & Jacky W. Y. Lam & Jianwei Sun & Haoke Zhang & Ben Zhong Tang, 2023. "Regulating the proximity effect of heterocycle-containing AIEgens," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    3. Onur Yildirim & Matteo Bonomo & Nadia Barbero & Cesare Atzori & Bartolomeo Civalleri & Francesca Bonino & Guido Viscardi & Claudia Barolo, 2020. "Application of Metal-Organic Frameworks and Covalent Organic Frameworks as (Photo)Active Material in Hybrid Photovoltaic Technologies," Energies, MDPI, vol. 13(21), pages 1-48, October.
    4. Minghui Liu & Youxing Liu & Jichen Dong & Yichao Bai & Wenqiang Gao & Shengcong Shang & Xinyu Wang & Junhua Kuang & Changsheng Du & Ye Zou & Jianyi Chen & Yunqi Liu, 2022. "Two-dimensional covalent organic framework films prepared on various substrates through vapor induced conversion," Nature Communications, Nature, vol. 13(1), pages 1-9, December.

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