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

Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

5.3K
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...
5.3K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.6K
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...
2.6K
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
π Molecular Orbitals of the Allyl Radical01:27

π Molecular Orbitals of the Allyl Radical

4.7K
Allyl radicals are three-carbon conjugated systems. They are readily formed as intermediates in halogenation reactions of alkenes involving the addition of halogen to the allylic carbon instead of the double bond. As seen in allyl cations and anions, each of the three sp2-hybridized carbon atoms in allyl radicals has an unhybridized p orbital. These orbitals combine to give three π molecular orbitals.
The allyl systems have identical molecular orbitals but differ in the number of π electrons....
4.7K
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
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

Ring Contraction of Cyclooctatetraenes toward Non-Benzenoid Polycyclic Aromatic Hydrocarbons by Au(111)-Catalysis and Bulk Pyrolysis.

Chemistry (Weinheim an der Bergstrasse, Germany)·2025
Same author

Steering Magnetic Coupling in Diradical Nonbenzenoid Nanographenes.

Journal of the American Chemical Society·2025
Same author

Exceptionally High Two-Photon Absorption Cross Sections in Quinoidal Diazaacene-Bithiophene Derivatives.

Angewandte Chemie (International ed. in English)·2025
Same author

Diels-Alder Reactivity of Triisopropylsilyl Ethynyl Substituted Acenes.

Chemistry (Weinheim an der Bergstrasse, Germany)·2024
Same author

Impact of Calcium and Phosphorus Levels on Optical Deterioration in Primary and Secondary Intraocular Lens Calcification.

Translational vision science & technology·2024
Same author

Breaking Strong Alkynyl-Phenyl Bonds: Poly(<i>para</i>-phenylene ethynylene)s under Mechanical Stress.

Journal of the American Chemical Society·2024
Same journal

Proton Transfer Shuttle Mediated Dormant-Active Balance for Accelerated and Controlled Polymerization of N-Carboxyanhydrides.

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

Chloride-Regulated Depolymerization of Aluminosilicate Networks for Fast Ion Transport Compliant Interfaces in Sustainable All-Solid-State Sodium Batteries.

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

Asymmetric Zn─N<sub>2</sub>O-Coordinated Hydrogen-Bonded Organic Frameworks for Electrochemical Hydrogen Peroxide Production and Wastewater Purification.

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

Photocatalytic Cascade Nitrogen Fixation for Selective Purification of Methane-Rich Coal-Bed Gas Over a Bimetallic MOF.

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

Scalable Art-Inspired Tessellated Covalent Organic Framework Membranes Enable Highly Selective Ion Separation.

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

Layered Copper-Anthraquinone Coordination Polymer Cathode Leveraging Dual-Redox Sites and Facilitated Ion Diffusion for High-Performance Lithium-Ion Batteries.

Angewandte Chemie (International ed. in English)·2026
See all related articles

Related Experiment Video

Updated: Mar 18, 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

11.8K

A Stable π-Conjugated Singlet Biradical.

Felix Hinkel1,2, Jan Freudenberg1,3, Uwe H F Bunz4,5

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Angewandte Chemie (International Ed. in English)
|June 28, 2016
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a large polycyclic hydrocarbon exhibiting a singlet biradical ground state. This was achieved through specific molecular design, stabilizing its unique electronic configuration for potential applications in materials science.

Keywords:
aromaticitypolycyclesquinoidsradicalszethrenes

More Related Videos

Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional &#960;-conjugate Systems
09:57

Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional π-conjugate Systems

Published on: February 10, 2020

7.7K
Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

9.1K

Related Experiment Videos

Last Updated: Mar 18, 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

11.8K
Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional &#960;-conjugate Systems
09:57

Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional π-conjugate Systems

Published on: February 10, 2020

7.7K
Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

9.1K

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Quantum Chemistry

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are fundamental organic molecules with diverse electronic properties.
  • Understanding and controlling the ground state electronic configuration of large PAHs is crucial for developing novel materials.
  • Open-shell singlet states in organic molecules are of significant interest due to their unique reactivity and potential applications.

Purpose of the Study:

  • To synthesize and characterize a large polycyclic hydrocarbon with a singlet biradical ground state.
  • To investigate the role of molecular topology and substituents in stabilizing open-shell singlet states.
  • To explore the potential of such molecules in advanced materials and chemical applications.

Main Methods:

  • Rational molecular design incorporating specific topological features.
  • Synthesis of a novel large polycyclic hydrocarbon structure.
  • Spectroscopic and computational analyses to determine the ground state electronic configuration.

Main Results:

  • Successful synthesis of a large polycyclic hydrocarbon featuring a singlet biradical ground state.
  • Demonstration that molecular topology and electron-accepting substituents are key factors in stabilizing the open-shell singlet state.
  • Characterization confirmed the unique electronic structure and stability of the synthesized molecule.

Conclusions:

  • The study successfully achieved a large polycyclic hydrocarbon with a stable singlet biradical ground state.
  • Molecular architecture, specifically topology and substituent effects, plays a critical role in controlling the electronic ground state of complex organic molecules.
  • This work opens new avenues for designing and synthesizing novel organic materials with tailored electronic properties.