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

Li, Xinle; Zhang, Changlin; Cai, Songliang; Lei, Xiaohe; Altoe, Virginia; Hong, Fang; Urban, Jeffrey J.; Ciston, Jim; Chan, Emory M.; Liu, Yi

doi:10.1038/s41467-018-05462-4

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

Journal Article · 31 July 2018 · Nature Communications

DOI: https://doi.org/10.1038/s41467-018-05462-4 · OSTI ID:1461610

Li, Xinle ^[1];

^[1]; Cai, Songliang ^[2]; Lei, Xiaohe ^[3]; Altoe, Virginia ^[1]; Hong, Fang ^[4]; Urban, Jeffrey J. ^[1]; Ciston, Jim ^[1]; Chan, Emory M. ^[1];

^[1]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry
South China Normal Univ., Guangzhou (China). School of Chemistry and Environment
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Molecular Foundry; Zhejiang Univ., Hangzhou (China). Dept. of Chemistry
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). The Advanced Light Source

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.

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Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); National Natural Science Foundation of China (NSFC); USDOE

Grant/Contract Number:: AC02-05CH11231; 21603076

OSTI ID:: 1461610

Alternate ID(s):: OSTI ID: 1477418

Journal Information:: Nature Communications, Vol. 9; ISSN 2041-1723

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United States

Language:: English

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Toward Covalent Organic Frameworks Bearing Three Different Kinds of Pores: The Strategy for Construction and COF-to-COF Transformation via Heterogeneous Linker Exchange Qian, Cheng; Qi, Qiao-Yan; Jiang, Guo-Fang Journal of the American Chemical Society, Vol. 139, Issue 19 https://doi.org/10.1021/jacs.7b02303	journal	May 2017
Solution Synthesis of Semiconducting Two-Dimensional Polymer via Trimerization of Carbonitrile Liu, Jingjing; Zan, Wu; Li, Ke Journal of the American Chemical Society, Vol. 139, Issue 34 https://doi.org/10.1021/jacs.7b05025	journal	July 2017
Synthesis of Ultrafine and Highly Dispersed Metal Nanoparticles Confined in a Thioether-Containing Covalent Organic Framework and Their Catalytic Applications Lu, Shuanglong; Hu, Yiming; Wan, Shun Journal of the American Chemical Society, Vol. 139, Issue 47 https://doi.org/10.1021/jacs.7b07918	journal	November 2017
Benzoxazole-Linked Ultrastable Covalent Organic Frameworks for Photocatalysis Wei, Pi-Feng; Qi, Ming-Zhu; Wang, Zhi-Peng Journal of the American Chemical Society, Vol. 140, Issue 13 https://doi.org/10.1021/jacs.8b00571	journal	March 2018
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Oriented Thin Films of a Benzodithiophene Covalent Organic Framework Medina, Dana D.; Werner, Veronika; Auras, Florian ACS Nano, Vol. 8, Issue 4 https://doi.org/10.1021/nn5000223	journal	March 2014
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Pore surface engineering in covalent organic frameworks Nagai, Atsushi; Guo, Zhaoqi; Feng, Xiao Nature Communications, Vol. 2, Issue 1 https://doi.org/10.1038/ncomms1542	journal	September 2011
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Tessellated multiporous two-dimensional covalent organic frameworks Jin, Yinghua; Hu, Yiming; Zhang, Wei Nature Reviews Chemistry, Vol. 1, Issue 7 https://doi.org/10.1038/s41570-017-0056	journal	July 2017
The atom, the molecule, and the covalent organic framework Diercks, Christian S.; Yaghi, Omar M. Science, Vol. 355, Issue 6328 https://doi.org/10.1126/science.aal1585	journal	March 2017

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