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

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.0K
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.
10.0K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.8K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.8K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.1K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.1K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.2K
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...
2.2K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control01:23

Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control

2.5K
The addition of a hydrogen halide to 1,3-butadiene gives a mixture of 1,2- and 1,4-adducts. Since more substituted alkenes are more stable, the 1,4-adduct is expected to be the major product. However, the product distribution is strongly influenced by temperature; low temperature favors the 1,2-adduct, whereas the 1,4-adduct is predominant at high temperature.
2.5K

You might also read

Related Articles

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

Sort by
Same author

Strategic Modulation of Phenothiazine-Based Self-Assembled Monolayers for Optimized Energy-Level Alignment and Stability in Perovskite Solar Cells.

ACS applied materials & interfaces·2026
Same author

Orbital-Hybridizable Nanoseed Interphase Enables One-Minute Rechargeable, Energy-Dense Anode-Free Aqueous Zinc Batteries.

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

Synergistic Bimolecular Passivation Enabling High-Performance Inverted Perovskite Solar Cells.

ACS applied materials & interfaces·2026
Same author

Iterative Synthesis of Pentacene Derivatives with Continuous Boron-Oxygen Bonds.

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

Electronic Spin State Determines Bidirectional Catalysis of Dual-Atom Catalysts in Sulfur Cathodes.

ACS applied materials & interfaces·2026
Same author

Dynamic Microinterfacial Polymerization Enables Scalable Synthesis of Two-Dimensional Polymer Sheets for Quasi-Solid-State Electrolytes in Sodium-Metal Batteries.

Angewandte Chemie (International ed. in English)·2026

Related Experiment Video

Updated: Jun 4, 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

9.5K

Achieving Precise Control Over the Molecular Periphery of Dibenzoixenes Through Modular Synthesis.

Seongrok Shin1, Hwon Kim1, Jee Ho Ha2

  • 1Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan, 44919, Republic of Korea.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 23, 2024
PubMed
Summary

Researchers synthesized dibenzoixenes with controlled edge structures, revealing their impact on optoelectronic and magnetic properties. These materials show potential for organic electronics and Li-ion batteries.

Keywords:
fused-ring systemsmolecular diversitynanostructurespolycyclessemiconductors

More Related Videos

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.8K

Related Experiment Videos

Last Updated: Jun 4, 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

9.5K
Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

6.9K
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
05:15

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

6.8K

Area of Science:

  • Organic electronics
  • Materials science
  • Supramolecular chemistry

Background:

  • Finite graphene forms like nanographenes and polycyclic aromatic hydrocarbons are promising organic semiconductors.
  • Their properties are tunable via molecular periphery control, but edge structures lack systematic study.

Purpose of the Study:

  • To achieve rational design and synthesis of isomeric dibenzoixenes with diverse molecular peripheries.
  • To systematically elucidate the molecular-level edge topologies and their structure-property relationships.

Main Methods:

  • Modular synthesis of dibenzoixenes with cove, zigzag, bay, fjord, and gulf edges.
  • Single-crystal X-ray diffraction for structural determination.
  • Fourier transform infrared spectroscopy and density functional theory for edge structure identification.
  • Electron spin resonance spectroscopy for magnetic properties.
  • Electrochemical analysis for Li-ion battery applications.

Main Results:

  • Synthesized isomeric dibenzoixenes with diverse edge structures.
  • Determined single-crystal structures revealing enantiomeric pairs with helically twisted cove edges.
  • Identified edge structures using vibrational modes and DFT calculations.
  • Observed significant impact of zigzag edges on magnetic properties.
  • Dibenzo[a,p]ixene showed promising Li intercalation with ~120 mAh/g capacity.

Conclusions:

  • Established modular syntheses for dibenzoixenes with engineered peripheries.
  • Demonstrated structure-property correlations for optoelectronic and magnetic applications.
  • Highlighted potential for developing larger π-extended systems for organic electronics and energy storage.