Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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 position.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Polyolefin cyclization triggered by electrochemically generated alkoxycarbenium ions: batch and flow conditions.

Chemical science·2026
Same author

Flow-Microreactor-Enabled Chemoselective Anionic Polymerization of Styrenes Bearing Alkoxysilyl Groups.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Real-Time Visualization of Turbulent Micromixing in a T-Mixer: Submillisecond Homogenization Revealed by Chemiluminescence.

Analytical chemistry·2026
Same author

Anion Mask Strategy Enabling Organolithium Species Bearing Formyl Groups: Protecting-Group-Free Synthesis for Unsymmetric Dicarbonyl Arenes.

The Journal of organic chemistry·2026
Same author

Kinetic resolution of racemic planar-chiral vinylcymantrenes by molybdenum-catalyzed asymmetric metathesis dimerization.

Beilstein journal of organic chemistry·2026
Same author

Water-compatible acylation reactions with acid chlorides using a flow microreactor.

Chemical communications (Cambridge, England)·2026

Related Experiment Video

Updated: May 24, 2026

A 'Plug and Play' Method to Create Water-dispersible Nanoassemblies Containing an Amphiphilic Polymer, Organic Dyes and Upconverting Nanoparticles
12:51

A 'Plug and Play' Method to Create Water-dispersible Nanoassemblies Containing an Amphiphilic Polymer, Organic Dyes and Upconverting Nanoparticles

Published on: November 14, 2015

Development of Azulene-Based Chromophore for Color-Responsive Self-Assembly Enabled by Flow Chemistry.

Shigeharu Wakabayashi1, Ryuhei Kikuchi2, Hiroki Soutome2

  • 1Department of Clinical Nutrition, Faculty of Health Science, Suzuka University of Medical Science, Suzuka, Mie 510-0293, Japan.

The Journal of Organic Chemistry
|May 22, 2026
PubMed
Summary

Flow microreactors enable controlled functionalization of azulene by stabilizing reactive intermediates. This breakthrough allows for the synthesis of novel azulene derivatives and real-time monitoring of supramolecular switching for responsive materials.

More Related Videos

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

Related Experiment Videos

Last Updated: May 24, 2026

A 'Plug and Play' Method to Create Water-dispersible Nanoassemblies Containing an Amphiphilic Polymer, Organic Dyes and Upconverting Nanoparticles
12:51

A 'Plug and Play' Method to Create Water-dispersible Nanoassemblies Containing an Amphiphilic Polymer, Organic Dyes and Upconverting Nanoparticles

Published on: November 14, 2015

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Azulene functionalization is challenging due to the instability of lithiated intermediates.
  • Developing controlled methods for synthesizing substituted azulenes is crucial for materials applications.

Purpose of the Study:

  • To demonstrate the utility of flow microreactors for controlled azulene functionalization.
  • To synthesize and characterize novel azulene-based supramolecular assemblies.
  • To investigate real-time supramolecular switching for color-responsive materials.

Main Methods:

  • Utilizing flow microreactors for rapid mixing, short residence times, and precise temperature control.
  • Regioselective synthesis of 6- and 1-substituted azulenes.
  • Characterization of self-assembled cyclic trimers and their disassembly.

Main Results:

  • Achieved regioselective azulene functionalization up to 89% yield under noncryogenic conditions.
  • Synthesized a 6-diethylboryl-1-(pyridin-4-yl)azulene that self-assembles into a cyclic trimer.
  • Observed a blue shift in the trimer and a red-shifted disassembly upon addition of 4-dimethylaminopyridine (DMAP).
  • Monitored DMAP-induced supramolecular disassembly in real time using in-line UV-vis spectroscopy.

Conclusions:

  • Flow microreactors overcome limitations in azulene chemistry by stabilizing reactive intermediates.
  • Developed a method for synthesizing stimuli-responsive azulene-based supramolecular materials.
  • Demonstrated real-time visualization of supramolecular switching, paving the way for color-responsive functional materials.