Cyanurate-Linked Covalent Organic Frameworks Enabled by Dynamic Nucleophilic Aromatic Substitution

J Am Chem Soc. 2022 Oct 5;144(39):17737-17742. doi: 10.1021/jacs.2c00778. Epub 2022 Sep 27.

Abstract

We report, for the first time, highly crystalline cyanurate-linked covalent organic frameworks synthesized via dynamic nucleophilic aromatic substitution. The high crystallinity is enabled by the bond exchange reaction (self-correction) between 2,4,6-triphenoxy-1,3,5-triazine and diphenols via reversible SNAr catalyzed by triazabicyclodecene. The CN-COFs contain flexible backbones that exhibit a unique AA'-stacking due to interlayer hydrogen bonding interactions. The isoreticular expansion study demonstrates the general applicability of this synthetic method. The resulting CN-COFs exhibited good stability, as well as high CO2/N2 selectivity.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Carbon Dioxide
  • Metal-Organic Frameworks*
  • Triazines

Substances

  • Metal-Organic Frameworks
  • Triazines
  • Carbon Dioxide