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

Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

2.9K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
2.9K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.0K
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...
3.0K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.2K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.2K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.3K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.3K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K

You might also read

Related Articles

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

Sort by
Same author

Unforgeable Red: Design and Application of SO-Annulated Perylene Diimides for Anti-Counterfeiting.

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

From Yellow to Red: Emission Tuning of Benzothioxanthene Imides Through Selective Multi-Arylamine Functionalization.

ChemPlusChem·2026
Same author

Amine-Triggered Azabenz-Annulation of Cyclic Secondary Amine-Functionalized Perylene Diimides for Dual-Mode Sensing.

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

Tunable thermochromism in N-annulated perylene diimide thin films.

Chemical communications (Cambridge, England)·2026
Same author

An Ammonium-Amino-Functionalized N-Annulated Perylene Diimide as a High-Performance Interlayer for Organic Photovoltaics.

ACS applied materials & interfaces·2026
Same author

Exploring the limits of inductive electron withdrawal in fused bicyclic azaheterocycles.

Chemical communications (Cambridge, England)·2025

Related Experiment Video

Updated: Jul 31, 2025

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

9.6K

New Generation of Benzidine Wide-Gap Conjugated Materials: Solution Processing a Classic Evaporated Scaffold.

Pablo Simón Marqués1, Akpeko Gasonoo1, Kathryn Wolfe1

  • 1Department of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, T2N 1N4, Canada.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 3, 2023
PubMed
Summary

Researchers developed new organic semiconductors by modifying carbazole and fluorene blocks. These materials show enhanced solubility in green solvents, enabling efficient fabrication of organic electronic devices like light-emitting diodes.

Keywords:
benzidinesblue emittersgreen solventsmolecular engineeringslot-die coating

More Related Videos

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

14.0K
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

17.2K

Related Experiment Videos

Last Updated: Jul 31, 2025

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
08:51

Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core

Published on: October 24, 2017

9.6K
Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
10:16

Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties

Published on: January 8, 2016

14.0K
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

17.2K

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Organic Electronics

Background:

  • Benzidine derivatives are crucial in organic electronics.
  • Improving solubility in green solvents is essential for sustainable device fabrication.
  • Current organic semiconductors often require harsh solvents or vacuum processing.

Purpose of the Study:

  • To synthesize novel carbazole- and fluorene-substituted benzidine derivatives.
  • To enhance the solubility of these organic semiconductors in greener solvents.
  • To investigate the structure-solubility relationship for tailored material design.

Main Methods:

  • Functionalization of benzidine blocks with pendant groups (glycol and ionic chains).
  • Solubility testing in various green solvents (o-xylenes, alcohols).
  • Fabrication of organic electronic devices, including slot-die coated films and organic light-emitting diodes (OLEDs).

Main Results:

  • Achieved high solubility (up to 150 mg/mL in o-xylenes) for glycol-containing materials.
  • Demonstrated good solubility in alcohols for ionic chain-functionalized compounds.
  • Successfully fabricated large-area (33 cm × 2 cm) luminescence films using slot-die coating.
  • Implemented materials in OLEDs exhibiting low turn-on voltage (4 V), comparable to vacuum-processed devices.

Conclusions:

  • A structure-solubility relationship was established, enabling tailored design of organic semiconductors.
  • The developed materials offer a viable alternative to vacuum-processed devices for organic electronics.
  • The synthetic strategy facilitates adaptation of solubility for specific solvents and applications.