Related Experiment Video
Updated: Aug 27, 2025

Synthesis and Characterization of Functionalized Metal-organic Frameworks
Published on: September 5, 2014
Cyanurate-Linked Covalent Organic Frameworks Enabled by Dynamic Nucleophilic Aromatic Substitution
Zepeng Lei1, Lacey J Wayment1, Jackson R Cahn1
1Department of Chemistry, University of Colorado Boulder, Boulder, Colorado 80309, United States.
Highly crystalline cyanurate-linked covalent organic frameworks (CN-COFs) were synthesized using a dynamic nucleophilic aromatic substitution method. This approach yields stable materials with excellent carbon dioxide selectivity, demonstrating broad applicability.
Area of Science:
- Materials Science
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Covalent Organic Frameworks (COFs) are crystalline porous polymers.
- Achieving high crystallinity in COFs can be challenging.
- Dynamic covalent chemistry offers pathways for self-correction and improved crystallinity.
Purpose of the Study:
- To report the first synthesis of highly crystalline cyanurate-linked COFs.
- To investigate the use of dynamic nucleophilic aromatic substitution (SNAr) for COF synthesis.
- To explore the structural features and properties of the synthesized CN-COFs.
Main Methods:
- Utilizing reversible SNAr reactions catalyzed by triazabicyclodecene.
- Employing 2,4,6-triphenoxy-1,3,5-triazine and diphenols as building blocks.
- Conducting isoreticular expansion studies to demonstrate synthetic versatility.
Main Results:
- Achieved highly crystalline cyanurate-linked COFs through a self-correction mechanism.
- Observed unique AA'-stacking in the flexible backbones due to hydrogen bonding.
- Demonstrated general applicability of the synthetic method via isoreticular expansion.
- Synthesized CN-COFs exhibited good stability and high CO2/N2 selectivity.
Conclusions:
- Dynamic SNAr chemistry is a viable strategy for synthesizing highly crystalline COFs.
- The developed method provides access to robust CN-COFs with tunable structures.
- These materials show promise for carbon capture applications due to selective CO2 adsorption.
More Related Videos
09:34Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
08:42Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
Published on: July 10, 2017
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Electrophilic Aromatic Substitution: Overview
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3