Multistep Solid-State Organic Synthesis of Carbamate-Linked Covalent Organic Frameworks.

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ID: 1464
2019
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Abstract
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 postsynthetic 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 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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lyle2019multistep Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Lyle, Steven J;Osborn Popp, Thomas M;Waller, Peter J;Pei, Xiaokun;Reimer, Jeffrey A;Yaghi, Omar M;
Journal Journal of the American Chemical Society
Year 2019
DOI
10.1021/jacs.9b04731
URL
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