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

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.4K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
9.4K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.6K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.6K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.3K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.3K
Radical Formation: Addition00:47

Radical Formation: Addition

1.9K
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...
1.9K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.2K
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...
2.2K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.6K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.6K

You might also read

Related Articles

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

Sort by
Same author

Molecular Conformation-Locking for Eye Care and Highly Efficient Narrowband Deep-Blue Organic Electroluminescence.

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

Organoboron Cycloarenes: Boron-Carbon Annulated Macrocyclic π-Systems.

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

Boracycle-Annulation Stabilizes Antiaromaticity and Enhances Diradical Character in s-Indacene/Dicyclopenta[b,g]Naphthalene-Cored Organoboron Polycyclic Hydrocarbons.

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

Lateral Boron-Doping Intensifies Diradical State and Stabilizes Spins of <i>peri</i>-Acenoacene: A Nanographene Diradicaloid with Absorption beyond 1300 nm.

Journal of the American Chemical Society·2026
Same author

Efficient pure-red multiple resonance emitter based on a donor planarization strategy.

Chemical science·2026
Same author

Vibrational-State-Regulated Hot-Band Thermal Activation for Anti-Stokes Luminescence.

The journal of physical chemistry letters·2026

Related Experiment Video

Updated: May 5, 2026

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

11.0K

Boron-Containing Organic Diradicaloids: Dynamically Modulating Singlet Diradical Character by Lewis Acid-Base

Jiaxiang Guo1, Yue Yang1, Chuandong Dou1

  • 1State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, People's Republic of China.

Journal of the American Chemical Society
|October 19, 2021
PubMed
Summary

Researchers developed stable boron-containing organic diradicaloids with unique electronic and magnetic properties. These novel materials exhibit Lewis acidity and dynamic modulations of diradical character, opening new avenues in organic electronics.

More Related Videos

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.1K
Author Spotlight: Magnetometric Characterization of Intermediates in the Solid-State Electrochemistry of Redox-Active Metal-Organic Frameworks
06:53

Author Spotlight: Magnetometric Characterization of Intermediates in the Solid-State Electrochemistry of Redox-Active Metal-Organic Frameworks

Published on: June 9, 2023

2.5K

Related Experiment Videos

Last Updated: May 5, 2026

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

11.0K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.1K
Author Spotlight: Magnetometric Characterization of Intermediates in the Solid-State Electrochemistry of Redox-Active Metal-Organic Frameworks
06:53

Author Spotlight: Magnetometric Characterization of Intermediates in the Solid-State Electrochemistry of Redox-Active Metal-Organic Frameworks

Published on: June 9, 2023

2.5K

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Organic diradicaloids possess unique open-shell structures crucial for organic electronics and spintronics.
  • Incorporating heteroatoms modifies electronic structures, but boron-containing diradicaloids are challenging due to high reactivity.

Purpose of the Study:

  • To synthesize and characterize novel, stable boron-containing organic diradicaloids.
  • To explore their magnetic, optoelectronic, and Lewis acidic properties.

Main Methods:

  • Synthesis of two isomeric boron-containing polycyclic hydrocarbons (PHs) by incorporating planarized triarylboranes into indenofluorene π-skeletons.
  • Theoretical calculations and experimental characterization to confirm structures and properties.

Main Results:

  • Synthesized stable, ambient-compatible boron-containing organic diradicaloids with open-shell singlet diradical structures.
  • Observed unique magnetic properties (thermally accessible triplet species) and optoelectronic characteristics (narrow energy gaps).
  • Demonstrated significant Lewis acidity and the ability to form Lewis adducts, dynamically modulating aromaticity and diradical character.

Conclusions:

  • Successfully synthesized stable boron-containing organic diradicaloids, overcoming previous reactivity challenges.
  • These compounds exhibit unprecedented Lewis acidity and dynamic control over diradical character.
  • The findings offer new possibilities for advanced organic electronic and spintronic applications.