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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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...
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
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Organic compounds with conjugated double bonds show strong absorption features in the UV–visible region of the electromagnetic spectrum attributed to π → π* electronic excitations. Generally, a UV–vis absorption spectrum is recorded as a plot of absorbance vs wavelength. The wavelength of maximum absorbance, which manifests as a peak in the absorption spectrum, is denoted as λmax.
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In Ultraviolet–Visible (UV–Vis) spectroscopy, the absorption of electromagnetic radiation is used to probe the electronic structure of molecules. This technique provides insights into molecular electronic transitions, particularly the movement of electrons between different molecular orbitals. Radiation is absorbed if the energy of the electromagnetic radiation passing through the molecule is precisely equal to the energy difference between the excited and ground states. During this...
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Related Experiment Video

Updated: Jul 7, 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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A Visible Light Responsive Smart Covalent Organic Framework with a Bridged Azobenzene Backbone.

Liang Qiang1, Hao Bai1, Xin-Yi Li1

  • 1Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, The Key Laboratory of Applied Chemistry of Chongqing Municipality, College of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, P. R. China.

Macromolecular Rapid Communications
|December 22, 2023
PubMed
Summary

Researchers created a novel porous material, COF-bAzo-TFPB, that responds to light. This covalent organic framework exhibits reversible photoisomerization, enabling applications in controlled release and UV-sensitive functions.

Keywords:
3,3′-diamino-2,2′-ethylene-bridged azobenzenecarbon dioxide capturecovalent organic frameworksreversible photoswitching

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Nanotechnology

Background:

  • Covalent organic frameworks (COFs) are crystalline porous polymers with tunable properties.
  • Developing stimuli-responsive COFs is crucial for advanced applications.
  • Azobenzene-containing materials offer photo-responsive capabilities.

Purpose of the Study:

  • To synthesize a novel visible light-responsive 2D covalent organic framework.
  • To investigate the photoisomerization behavior of the azobenzene unit within the framework.
  • To explore potential applications in photo-controlled processes.

Main Methods:

  • Condensation reaction between 3,3'-diamino-2,2'-ethylene-bridged azobenzene and 1,2,4,5-tetrakis-(4-formylphenyl) benzene.
  • Characterization of the resulting porous material (COF-bAzo-TFPB) for its structure, surface area, crystallinity, and stability.
  • Investigation of the photoisomerization of the incorporated azo units under visible light irradiation.

Main Results:

  • Successful synthesis of COF-bAzo-TFPB, a 2D porous covalent organic framework.
  • The material exhibits a large surface area, good crystallinity, and notable thermal and chemical stability.
  • The azo units within the COF-bAzo-TFPB skeleton demonstrate reversible photoisomerization upon visible light exposure.

Conclusions:

  • The designed linker enables photo-responsive behavior in the COF-bAzo-TFPB.
  • This work expands the utility of covalent organic frameworks for photo-controlled release, guest molecule uptake, and dynamic photoswitching.
  • The developed material shows promise for UV-sensitive applications.