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

Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

8.1K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
8.1K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

4.7K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
4.7K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

13.6K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
13.6K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

12.9K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
12.9K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

12.5K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
12.5K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.2K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
4.2K

You might also read

Related Articles

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

Sort by
Same author

Iterative Synthesis of Pyrene-Coronene Molecular Graphene Nanoribbons.

Angewandte Chemie (International ed. in English)·2026
Same author

A Negatively Curved Pyrene-Fused Azaacene.

Angewandte Chemie (International ed. in English)·2026
Same author

Mechanistic Insights into Layered Growth of Imine-Linked Bilayer 2D Covalent Organic Frameworks.

Journal of the American Chemical Society·2026
Same author

High Charge Carrier Mobility in Non-Conjugated 3D Covalent Organic Frameworks.

Advanced materials (Deerfield Beach, Fla.)·2026
Same author

Why covalent organic frameworks grow twisted on graphite.

Nature communications·2025
Same author

POM-Based Water Splitting Catalyst Under Acid Conditions Driven by Its Assembly on Carbon Nanotubes.

Advanced materials (Deerfield Beach, Fla.)·2025

Related Experiment Video

Updated: Mar 15, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.8K

K-Conjugated Dibenzoazahexacenes.

Gabriella Antonicelli1, Cristian Gozalvez1, Ainhoa Atxabal2

  • 1POLYMAT, University of the Basque Country UPV/EHU , Avenida de Tolosa 72, E-20018 Donostia-San Sebastián, Spain.

Organic Letters
|September 8, 2016
PubMed
Summary

Two novel K-conjugated dibenzoazahexacenes exhibit excellent stability and favorable molecular packing for efficient charge transport. Their electronic properties, particularly hole or electron transport, are tunable by altering the nitrogen atom content within the aromatic structure.

More Related Videos

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

12.2K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.9K

Related Experiment Videos

Last Updated: Mar 15, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.8K
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

12.2K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.9K

Area of Science:

  • Organic electronics
  • Materials science
  • Supramolecular chemistry

Background:

  • K-conjugated systems are crucial for organic electronic devices.
  • Dibenzoazahexacenes offer a promising scaffold for high-performance organic semiconductors.
  • Tuning molecular structure is key to controlling charge transport properties.

Purpose of the Study:

  • To synthesize and characterize novel K-conjugated dibenzoazahexacenes.
  • To investigate the relationship between molecular structure and charge transport.
  • To explore the potential of these materials in organic electronics.

Main Methods:

  • Single-crystal X-ray diffraction for structural analysis.
  • Optoelectronic and electrochemical characterization to determine electronic properties.
  • Theoretical calculations to understand molecular orbital alignment and packing.
  • Electrical device characterization to assess charge transport behavior.

Main Results:

  • Successful synthesis of two highly stable K-conjugated dibenzoazahexacenes.
  • Demonstrated favorable molecular packing and optimal frontier orbital energy alignment for charge transport.
  • Observed preferential transport of holes or electrons, dependent on the number of nitrogen atoms in the framework.

Conclusions:

  • The synthesized dibenzoazahexacenes are promising candidates for organic electronic applications.
  • Molecular design, specifically nitrogen incorporation, offers a strategy to control charge carrier mobility.
  • These findings contribute to the development of advanced organic semiconductor materials.