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

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, Jia Gao and Donglin Jiang ()
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Jia Guo: Institute for Molecular Science, National Institutes of Natural Sciences
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
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
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

Nature Communications, 2013, vol. 4, issue 1, 1-8

Abstract: 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.

Date: 2013
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DOI: 10.1038/ncomms3736

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