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 Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.0K
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...
3.0K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
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...
2.9K
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

5.9K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
5.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.7K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.7K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

11.2K
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...
11.2K
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.2K
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,...
4.2K

You might also read

Related Articles

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

Sort by
Same author

Charging Pyracylene: Steering Aromaticity and Reactivity of [12]Annulene by Substitution.

Journal of the American Chemical Society·2026
Same author

Post-Modification of Tripyrenylenes to Enantiopure π-Extended D<sub>3</sub>-Symmetric Propellers.

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

Copper-Catalyzed Domino Strategy Construction of Fused Benzopyrroloazepinone through the Reaction of Allenyloximes and Arylboronic Acids.

Organic letters·2026
Same author

Palladium-Catalyzed Approach to Highly Luminescent <i>para</i>-Difuropyrazines.

The Journal of organic chemistry·2026
Same author

Synthesis of Soft Octahedral Nanoparticles through Supramolecular Self-Assembly of <i>C</i><sub>3</sub>-Symmetric Trinaphthylamine Trisamides.

Journal of the American Chemical Society·2026
Same author

Toward Larger Cyclo-9,10-Anthryleneparaphenylenes.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026

Related Experiment Video

Updated: Sep 14, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.6K

C2-Symmetric Perylene-Embedded Double [5]Helicenes.

Asim Swain1, Frank Rominger1, Michael Mastalerz1

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

Organic Letters
|July 24, 2025
PubMed
Summary

Researchers synthesized a novel perylene-embedded double [5]helicene, enhancing chiroptical properties for circularly polarized materials. This new compound exhibits improved quantum yields and dissymmetry factors compared to pristine [5]helicene.

More Related Videos

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

8.0K
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

Related Experiment Videos

Last Updated: Sep 14, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

11.6K
Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

8.0K
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

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Chiroptical properties of polycyclic aromatic hydrocarbons (PAHs) are crucial for developing advanced circularly polarized materials.
  • Enhancing quantum yields and dissymmetry factors is essential for improving material performance.

Purpose of the Study:

  • To synthesize a novel [n]helicene-functionalized PAH with enhanced chiroptical properties.
  • To investigate the potential of perylene-embedded double [5]helicene for circularly polarized materials.

Main Methods:

  • A two-step synthesis involving Suzuki-Miyaura cross-coupling and base-catalyzed condensation.
  • Separation of enantiomers using chiral High-Performance Liquid Chromatography (HPLC).
  • Characterization of chiroptical properties, including quantum yield and dissymmetry factors (g_abs, g_lum).

Main Results:

  • Successful synthesis of a C2-symmetric perylene-embedded double [5]helicene with a configurational stability of 23 kcal mol⁻¹.
  • Separation of short-lived enantiomers was achieved.
  • The synthesized compound demonstrated significantly enhanced chiroptical properties compared to pristine [5]helicene, with a quantum yield of 0.7 and g_abs up to 8.8 × 10⁻³.

Conclusions:

  • The novel perylene-embedded double [5]helicene exhibits superior chiroptical performance.
  • This compound holds promise for the development of advanced circularly polarized materials.
  • The synthetic strategy provides a pathway for designing new helical PAHs with tailored optical properties.