期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 28, 页码 11253-11258出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b04731
关键词
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资金
- King Abdulaziz City for Science and Technology (Center of Excellence for Nanomaterials and Clean Energy Applications)
- Center for Gas Separations Relevant to Clean Energy Technologies, an Energy Frontier Research Center - U.S. Department of Energy, Office of Science, Basic Energy Sciences [DE-SC0001015]
- NSF
- Chevron-UC Berkeley Graduate Fellowship Program
- NIH [S10OD023532, S10 RR027172]
Herein, we demonstrate the first example of a multistep solid-state organic synthesis, in which a new imine-linked two-dimensional covalent organic framework (COF-170, 1) was transformed through three consecutive post-synthetic modifications into porous, crystalline cyclic carbamate and thiocarbamate-linked frameworks. These linkages are previously unreported and inaccessible through de novo synthesis. While not altering the overall connectivity of the framework, these chemical transformations induce significant conformational and structural changes at each step, highlighting the key importance of noncovalent interactions and conformational flexibility to COF crystallinity and porosity. These transformations were assessed using N-15 multiCP-MAS NMR spectroscopy, providing the first quantitation of yields in COF postsynthetic modification reactions, as well as of amine defect sites in imine-linked COFs. This multistep COF linkage postsynthetic modification represents a significant step toward bringing the precision of organic solution-phase synthesis to extended solid-state compounds.
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