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

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.5K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.5K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.5K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.5K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.3K
The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
2.3K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.3K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
2.3K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.1K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
2.1K
Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.1K

You might also read

Related Articles

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

Sort by
Same author

Through-Space Stabilization of Carbon-Centered Aryl Dicyanomethyl Radicals.

Journal of the American Chemical Society·2026
Same author

Light-Controlled Platelet Mechanics with Tunable BODIPY Photosensitizers.

Nano letters·2026
Same author

Breaking Bonds with Short-Wave Infrared Light: BODIPY Photocages for Two-Photon Activation in the 900-1500 nm NIR-II Window.

Journal of the American Chemical Society·2025
Same author

Phototoxicity of hydroxymethyl-BODIPYs: are photocages that innocent?

Chemical science·2025
Same author

Symmetry-breaking photoinduced charge transfer state in a near-IR absorbing <i>meso</i>-linked BODIPY dimer.

Physical chemistry chemical physics : PCCP·2025
Same author

A structurally compact aqueous soluble oxypicolinium photocage with high photosensitivity.

Chemical science·2025
Same journal

A General Photocatalytic Decarboxylative Hydrogenation of Carboxylic Acids in Batch and Flow under Metal-Free Conditions.

Organic letters·2026
Same journal

Direct Access to Sulfonamidated-1,4-Benzoquinones via Sulfonamidation of Aryl Alcohol-Derived Quinone Monoacetals.

Organic letters·2026
Same journal

Photo/Cerium Co-Catalyzed Hydroalkylation of Alkynes Via Decarboxylative Ring-Opening of Cyclic Carboxylic Acids.

Organic letters·2026
Same journal

Electrochemical Dehydroxylative Thiolation of Alkyl Alcohols with Disulfides.

Organic letters·2026
Same journal

Molybdenum-Catalyzed Intramolecular Deoxygenative Annulation of 2-(Formamido)aryl Ketones to Access 3-Monosubstituted Oxindoles.

Organic letters·2026
Same journal

Modular Synthesis of Spiroisochromans with Spiro Quaternary Carbon Centers Via TBAT-Promoted Multicomponent Cascade Reactions.

Organic letters·2026
See all related articles

Related Experiment Video

Updated: Dec 14, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.4K

Solvent-Responsive Radical Dimers.

Joshua P Peterson1, Arthur H Winter1

  • 1Department of Chemistry, Iowa State University, 1605 Gilman Hall, Ames, Iowa 50010, United States.

Organic Letters
|July 17, 2020
PubMed
Summary
This summary is machine-generated.

A novel aryl dicyanomethyl radical exhibits reversible switching between two distinct dimeric forms, a sigma dimer and a pi dimer, influenced by solvent polarity. This unique characteristic leads to observable solvatochromic effects, impacting optical properties.

More Related Videos

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

12.2K
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.6K

Related Experiment Videos

Last Updated: Dec 14, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.4K
Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

12.2K
Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
14:22

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development

Published on: April 15, 2013

20.6K

Area of Science:

  • Organic chemistry
  • Materials science
  • Photochemistry

Background:

  • Stable organic radicals are of interest for advanced materials.
  • Solvatochromism, the change in optical properties with solvent, is crucial for sensor development.

Purpose of the Study:

  • To synthesize and characterize a novel air- and thermally stable aryl dicyanomethyl radical.
  • To investigate the solvent-induced switching between different dimeric forms of the radical.
  • To explore the resulting solvatochromic behavior and its underlying mechanisms.

Main Methods:

  • Synthesis of the aryl dicyanomethyl radical.
  • Spectroscopic analysis (UV-Vis, NMR) to characterize radical forms.
  • Solvent variation studies to induce and observe dimer switching.

Main Results:

  • The aryl dicyanomethyl radical exists in two stable dimeric forms: a sigma dimer and a pi dimer.
  • Solvent polarity dictates the equilibrium between the sigma and pi dimers.
  • Distinct optical properties were observed for each dimer, leading to significant solvatochromic effects.

Conclusions:

  • The aryl dicyanomethyl radical demonstrates tunable optical properties through solvent manipulation.
  • The observed solvatochromism is attributed to the differential polarizability and stabilization of the pi dimer in polar solvents.
  • This radical system offers potential for applications in responsive materials and optical sensors.