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 & Donglin Jiang
Nature Communications 4, 2736
DOI: 10.1038/ncomms3736
Received: 10 May 2013
Accepted: 09 October 2013
Published: 13 November 2013

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.

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