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 Experiment Videos

Twin-rotor system created on a [4]radialene frame.

Yoshiyuki Kuwatani1, Gaku Yamamoto, Masahiko Iyoda

  • 1Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan.

Organic Letters
|September 12, 2003
PubMed
Summary

Researchers synthesized novel [4]radialenes with unique tricyclic ring structures. These compounds exhibit varying rotational barriers around butatriene bonds, influenced by steric interactions of terminal substituents like fluorene.

Related Concept Videos

You might also read

Related Articles

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

Sort by
Same author

Behavioral and Exumbrellar Integumental Defenses in Jellyfish: The Hydromedusan Spirocodon saltatrix Releases Oxidized Derivatives of Unsaturated Fatty Acids Potentially to Avoid Predation and Bacterial Biofouling.

Journal of chemical ecology·2026
Same author

Insights into the life cycles of trematodes infecting pelagic gastropods in Japan.

Journal of helminthology·2026
Same author

Neutrophil-Macrophage Interactions Shape Inflammatory Macrophage Remodeling in Gastric Cancer During Chemo-Immunotherapy.

Cancer science·2026
Same author

A cDC1-NK/T-Malignant Cell Circuit Drives Immunogenic Remodeling Under PD-1 Blockade in Gastric Cancer.

Cancer science·2026
Same author

A neustonic hydrozoan Porpita porpita drifts for over a year.

Scientific reports·2026
Same author

The migration of placenta even after 30 gestational weeks is a risk factor for postpartum hemorrhage.

AJOG global reports·2026

Area of Science:

  • Organic Chemistry
  • Materials Science

Background:

  • Extended [4]radialenes are complex organic molecules with unique electronic properties.
  • Tricyclic ring systems offer diverse structural possibilities for tuning molecular behavior.

Purpose of the Study:

  • To synthesize novel extended [4]radialenes featuring exocyclic butatriene units.
  • To investigate the impact of different tricyclic terminal substituents on the rotational dynamics of the butatriene core.

Main Methods:

  • Multi-step organic synthesis to construct the [4]radialene framework.
  • Variable temperature nuclear magnetic resonance (NMR) spectroscopy to study rotational barriers.
  • Computational analysis to understand steric and electronic effects.

Main Results:

Related Experiment Videos

  • Three extended [4]radialenes with thioxanthene, dihydroanthracene, and fluorene substituents were successfully synthesized.
  • Thioxanthene and dihydroanthracene analogues displayed rapid butatriene bond rotation (DeltaG() = 13.7 and 14.9 kcal/mol).
  • The fluorene-substituted analogue exhibited a significantly higher rotational barrier (DeltaG() = 17.8 kcal/mol) due to minimized ground-state steric repulsion.

Conclusions:

  • The rotational barrier of butatriene bonds in extended [4]radialenes is highly sensitive to the steric bulk of terminal substituents.
  • Steric interactions at the ground state play a crucial role in dictating the conformational dynamics of these molecules.