Related Experiment Video
Updated: Jan 4, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Amidation, Esterification, and Thioesterification of a Carboxyl-Functionalized Covalent Organic Framework
Lei Guo1,2, Shang Jia1, Christian S Diercks1,2
1Department of Chemistry, University of California-Berkeley, Berkeley, CA, 94720, USA.
Researchers developed new ways to modify a novel covalent organic framework (COF), COF-616, making it useful for removing water contaminants.
Area of Science:
- Materials Science
- Organic Chemistry
- Environmental Science
Background:
- Covalent organic frameworks (COFs) are crystalline porous materials with tunable properties.
- Post-synthetic modification (PSM) allows for the introduction of new functionalities onto existing COF structures.
- Developing efficient PSM strategies for COFs is crucial for expanding their applications.
Purpose of the Study:
- To demonstrate novel post-synthetic modification reactions on a two-dimensional COF, COF-616.
- To introduce a diverse range of functional groups onto COF-616 under mild conditions.
- To create functionalized COFs for effective water contaminant removal.
Main Methods:
- Three new PSM reactions (amidation, esterification, thioesterification) were performed on carboxyl-functionalized COF-616.
- Modifications were carried out under mild reaction conditions with high yields.
- Chelating functionalities were incorporated to create adsorbent materials.
Main Results:
- Successful amidation, esterification, and thioesterification of COF-616 were achieved.
- The PSM strategy allows for the introduction of various functional groups with high efficiency.
- The modified COF-616 demonstrated efficient removal of several water contaminants.
Conclusions:
- A versatile PSM strategy for COF-616 was established, enabling facile functionalization.
- The developed adsorbents show promise for environmental remediation applications.
- This work expands the utility of COFs in water purification technologies.
More Related Videos
Related Concept Videos
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
Amines to Amides: Acylation of Amines
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Preparation of Amides
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Amides to Carboxylic Acids: Hydrolysis
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Structures of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

