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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.4K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.4K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.9K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.9K
Structures of Carboxylic Acid Derivatives01:28

Structures of Carboxylic Acid Derivatives

3.5K
Structure 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...
3.5K
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

1.4K
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
1.4K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.1K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.1K
Nomenclature of Aryl and Heterocyclic Amines01:10

Nomenclature of Aryl and Heterocyclic Amines

2.8K
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
2.8K

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Related Experiment Video

Updated: Dec 1, 2025

Microfluidic-based Synthesis of Covalent Organic Frameworks COFs: A Tool for Continuous Production of COF Fibers and Direct Printing on a Surface
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Highly C2/C1-Selective Covalent Organic Frameworks Substituted with Azo Groups.

Shaofeng Huang1, Yiming Hu1, Li-Li Tan2

  • 1Department of Chemistry, University of Colorado, Boulder, Colorado 80309, United States.

ACS Applied Materials & Interfaces
|November 7, 2020
PubMed
Summary
This summary is machine-generated.

New covalent organic frameworks (AzoCOFs) show record-breaking selectivity for acetylene over methane separation. These stable, crystalline materials offer significant potential for industrial gas separation applications.

Keywords:
C2/C1 separationazo groupcovalent organic frameworkimine condensationselective gas adsorption

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Area of Science:

  • Materials Science
  • Chemical Engineering
  • Adsorption Science

Background:

  • Covalent organic frameworks (COFs) are crystalline porous polymers with tunable properties.
  • Efficient gas separation technologies are crucial for various industrial processes, including natural gas purification and petrochemicals.
  • Developing novel materials with high selectivity and stability for gas adsorption is an ongoing challenge.

Purpose of the Study:

  • To synthesize and characterize novel covalent organic frameworks substituted with azo groups (AzoCOFs).
  • To investigate the gas adsorption properties of AzoCOFs, particularly their selectivity for C2 hydrocarbons and CO2 over methane.
  • To explore the relationship between framework properties (pore size, polarity) and gas adsorption performance.

Main Methods:

  • Synthesis of AzoCOFs via imine condensation.
  • Characterization of crystallinity and stability of the synthesized frameworks.
  • Gas adsorption measurements and ideal adsorption solution theory (IAST) calculations to determine selectivity.

Main Results:

  • AzoCOFs were successfully synthesized with high crystallinity and stability.
  • Exceptional ideal adsorption solution theory (IAST) selectivity for acetylene (C2H2) over methane (CH4) was observed (35-2891).
  • The triethylene glycol substituted Tg-AzoCOF achieved the highest reported C2H2/CH4 selectivity (2891) among all porous materials.
  • High selectivity was also demonstrated for C2H4/CH4, C2H6/CH4, and CO2/CH4 separations.

Conclusions:

  • AzoCOFs exhibit outstanding performance in selective gas adsorption, particularly for C2H2/CH4 separation.
  • The favorable interactions between azo groups and acetylene molecules are key to the high selectivity.
  • AzoCOFs represent a promising class of materials for advanced gas separation applications.