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

Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.4K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
3.4K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.3K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.3K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.4K
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...
3.4K
Aromatic Compounds: Overview01:25

Aromatic Compounds: Overview

11.5K
In general, the term ‘aromatic’ indicates a pleasant smell or fragrance from fresh flowers, freshly prepared coffee, etc. In the early history of organic chemistry, many benzene derivatives were isolated from the pleasant odor oils of the plants. For example, vanillin was isolated from the oil of vanilla, methyl salicylate from the oil of wintergreen, and cinnamaldehyde from the oil of cinnamon. They all had a pleasant odor; hence the name aromatic was given.
In 1825, Faraday...
11.5K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

10.2K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or...
10.2K
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

2.3K
Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
2.3K

You might also read

Related Articles

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

Sort by
Same author

Association of Hemodynamic Disease Severity and Distribution With Risk of Future Acute Coronary Syndrome.

JACC. Cardiovascular imaging·2026
Same author

Acute coronary syndrome risk in coronary side branch versus main vessel lesions: Lumen, plaque, and hemodynamic insights from coronary CT angiography.

Journal of cardiovascular computed tomography·2026
Same author

Clinical outcomes following fractional flow reserve-guided revascularization using nicorandil versus conventional hyperemic agents: insights from the J-PRIDE Registry.

Cardiovascular intervention and therapeutics·2026
Same author

MUC4-Positive Fibroblastoma: Clinicopathological and Molecular Analysis of 7 Cases.

The American journal of surgical pathology·2026
Same author

Prognostic Impact of Renal Function on Outcomes After Physiology-Guided Coronary Revascularization: Insights From the J-PRIDE Registry.

Circulation. Cardiovascular interventions·2026
Same author

Supertrityl Radical and Cation: The Effect of a Large π-Surface for Intermolecular Interactions and Spin/Charge Delocalization.

Organic letters·2026

Related Experiment Video

Updated: Apr 21, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

5.7K

Phenalenyl-based open-shell polycyclic aromatic hydrocarbons.

Takashi Kubo1

  • 1Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka, 560-0043, Japan. kubo@chem.sci.osaka-u.ac.jp.

Chemical Record (New York, N.Y.)
|October 28, 2014
PubMed
Summary
This summary is machine-generated.

Phenalenyl radicals, a type of polycyclic aromatic hydrocarbon (PAH) radical, exhibit unique amphoteric redox properties and singlet biradical character. Their stability and intermolecular spin-spin coupling make them promising for advanced electroconductive and magnetic materials.

Keywords:
aromaticityhydrocarbonsphenalenylpolycyclesradicals

More Related Videos

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

7.4K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

7.7K

Related Experiment Videos

Last Updated: Apr 21, 2026

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

5.7K
Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

7.4K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

7.7K

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Quantum Chemistry

Background:

  • Phenalenyl radical is a stable polycyclic aromatic hydrocarbon (PAH) radical.
  • Its applications in electroconductive and magnetic materials are under investigation.
  • Strong intermolecular spin-spin coupling is a key characteristic.

Purpose of the Study:

  • To summarize studies on PAH radicals featuring the phenalenyl scaffold.
  • To explore their amphoteric redox properties.
  • To investigate their singlet biradical character.

Main Methods:

  • Analysis of electronic structure.
  • Evaluation of redox properties.
  • Characterization of spin states.

Main Results:

  • Phenalenyl radicals display amphoteric redox behavior.
  • A significant singlet biradical character was observed.
  • These properties are linked to the non-bonding character and symmetry of the singly occupied molecular orbital.

Conclusions:

  • The unique electronic structure of phenalenyl radicals dictates their properties.
  • Phenalenyl-based PAHs are promising for developing novel functional materials.
  • Further research into their electronic and magnetic properties is warranted.