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

Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons00:58

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

You might also read

Related Articles

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

Sort by
Same author

Asymmetric Diphosphane Dioxides With A-π-A-π'-D Scaffolds for High-Purity Deep-Blue Luminescence.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Magneto-Optical Correlations and Optical Signatures of Low-Coordinated and Highly Symmetrical Tb(III) Complexes.

Inorganic chemistry·2026
Same author

Boranil Chelates as Antennae for Ytterbium(III) Luminescence Sensitization.

Inorganic chemistry·2026
Same author

Ph<sub>2</sub>Si-bridged constrained-geometry complexes of hafnium and titanium for copolymerization of ethylene and 1-octene: an experimental and computational comparison.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Merging platinahelicene and nanographene: a strategy for circularly polarized phosphorescence in the near-infrared (NIR).

Chemical communications (Cambridge, England)·2026
Same author

Generation of mono(amino)carbenes from <i>N</i>-triftosyl amino hydrazonates with blue light.

Chemical communications (Cambridge, England)·2026

Related Experiment Video

Updated: Jun 6, 2026

An Electrochemical Cholesteric Liquid Crystalline Device for Quick and Low-Voltage Color Modulation
10:33

An Electrochemical Cholesteric Liquid Crystalline Device for Quick and Low-Voltage Color Modulation

Published on: February 27, 2019

Three-State Electrochiroptical Switches Derived from Chiral Stable Carbenes.

Patrick Yorkgitis1, Nicolas Vanthuyne2, Marie Cordier3

  • 1UCSD-CNRS Joint Research Laboratory (IRL 3555), Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093, United States.

Journal of the American Chemical Society
|June 4, 2026
PubMed
Summary

Chiral stable carbenes enable new three-state electrochiroptical switches. These switches utilize redox-driven changes in chirality for tunable electronic and optical properties in stimuli-responsive materials.

More Related Videos

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

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Related Experiment Videos

Last Updated: Jun 6, 2026

An Electrochemical Cholesteric Liquid Crystalline Device for Quick and Low-Voltage Color Modulation
10:33

An Electrochemical Cholesteric Liquid Crystalline Device for Quick and Low-Voltage Color Modulation

Published on: February 27, 2019

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

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Chiral redox switches are key for stimuli-responsive materials and organic electronics.
  • Stable carbenes are widely used in redox-active materials and asymmetric synthesis.
  • The integration of stable carbenes into chiral redox switches is an underexplored area.

Purpose of the Study:

  • To explore the use of chiral stable carbenes in constructing novel chiral redox switches.
  • To develop three-state electrochiroptical switches based on these new materials.
  • To demonstrate the tunable chiroptical properties driven by redox-induced chirality exchange.

Main Methods:

  • Synthesis of helically chiral overcrowded alkenes using chiral stable carbenes.
  • Electrochemical characterization to induce redox-driven (de)aromatization.
  • Chiroptical property measurements (electronic circular dichroism) to monitor chirality changes.

Main Results:

  • Successfully constructed helically chiral overcrowded alkenes that act as three-state switches.
  • Demonstrated reversible exchange between helical and axial chirality via a π-radical cation intermediate.
  • Observed distinct chiroptical properties for each state due to significant electronic and geometric structure changes, including chirality inversion.
  • Showcased multiple cycles of electrochemical ON-OFF switching and sign inversion of the circular dichroism response.

Conclusions:

  • Chiral stable carbenes are effective building blocks for chiral redox-switchable materials.
  • This work establishes a new platform for designing advanced electrochiroptical switches.
  • The developed materials offer promising applications in stimuli-responsive systems and organic electronics.