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

10.9K
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.
10.9K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.5K
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...
4.5K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

6.5K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
6.5K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.2K
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.
4.2K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.8K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.8K
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

3.2K
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
3.2K

You might also read

Related Articles

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

Sort by
Same author

Amine-reactive hydrogels via nucleophilic thiol-yne reaction: A functional scaffold for laccase immobilization and dye degradation.

International journal of biological macromolecules·2026
Same author

Engineering polymeric micelles for targeted drug delivery: "click" chemistry enabled bioconjugation strategies and emerging applications.

Journal of materials chemistry. B·2025
Same author

'Catch and Release' Polymeric Fibers: Versatile Interfaces for Engineering Reversible Platforms for Biomolecular Immobilization and Antibacterial Coatings.

Macromolecular bioscience·2025
Same author

Orthogonally Functionalizable Redox-Responsive Polymer Brushes: Catch and Release Platform for Proteins and Cells.

Journal of the American Chemical Society·2025
Same author

Stimuli-responsive polymers at the interface with biology.

Biomacromolecules·2025
Same author

Redox-Responsive Cleavable Polymeric Brush Coated Magnetic Nanoparticles: Fabrication and Post-Polymerization Modification for Cellular Targeting.

Biomacromolecules·2025

Related Experiment Video

Updated: Sep 22, 2025

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

13.8K

Diels-Alder "Clickable" Polymer Brushes: A Versatile Catalyst-Free Conjugation Platform.

Yasemin Nursel Yuksekdag1, Tugce Nihal Gevrek2, Amitav Sanyal2

  • 1Department of Chemistry and ‡Center for Life Sciences and Technologies, Bogazici University, Bebek, Istanbul 34342, Turkey.

ACS Macro Letters
|May 25, 2022
PubMed
Summary

This study introduces Diels-Alder cycloaddition for functionalizing polymer brushes, offering a mild, reagent-free method. This approach enables efficient conjugation of molecules onto furan-containing polymer brushes for diverse applications.

More Related Videos

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

24.8K
3D Printing and In Situ Surface Modification via Type I Photoinitiated Reversible Addition-Fragmentation Chain Transfer Polymerization
07:28

3D Printing and In Situ Surface Modification via Type I Photoinitiated Reversible Addition-Fragmentation Chain Transfer Polymerization

Published on: February 18, 2022

3.8K

Related Experiment Videos

Last Updated: Sep 22, 2025

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry
07:02

The Preparation and Properties of Thermo-reversibly Cross-linked Rubber Via Diels-Alder Chemistry

Published on: August 25, 2016

13.8K
Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
12:31

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

24.8K
3D Printing and In Situ Surface Modification via Type I Photoinitiated Reversible Addition-Fragmentation Chain Transfer Polymerization
07:28

3D Printing and In Situ Surface Modification via Type I Photoinitiated Reversible Addition-Fragmentation Chain Transfer Polymerization

Published on: February 18, 2022

3.8K

Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Surface Science

Background:

  • Polymeric brushes are crucial functional interfaces in materials and biomedical sciences.
  • Post-polymerization functionalization of reactive brushes offers facile access to tailored properties.
  • Click chemistry has been widely used for polymer brush functionalization.

Purpose of the Study:

  • To report the first use of Diels-Alder cycloaddition for polymer brush functionalization.
  • To demonstrate efficient conjugation of maleimide-containing molecules onto furan-containing polymer brushes.
  • To investigate a mild and reagent-free functionalization strategy.

Main Methods:

  • Grafting polymers with furan side chains from silicon oxide surfaces using atom transfer radical polymerization.
  • Incorporating furfuryl methacrylate and poly(ethylene glycol) methacrylate as comonomers.
  • Utilizing Diels-Alder cycloaddition for post-polymerization functionalization.

Main Results:

  • Successful functionalization of furan-containing polymer brushes via Diels-Alder reaction.
  • Mild and reagent-free conjugation conditions achieved.
  • Immobilization of various maleimide-containing molecules, including a model compound, fluorescent dye, and biotin ligand.

Conclusions:

  • Diels-Alder cycloaddition is an effective strategy for functionalizing polymer brushes.
  • This method allows for controlled immobilization of diverse molecules.
  • The developed approach offers a versatile platform for creating functional interfaces.