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

Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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...
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

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.
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...

You might also read

Related Articles

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

Sort by
Same author

Synthesis of polymethylene-linked bis(cyclobutane-fused chromanones) mediated by gold photocatalysis.

Organic & biomolecular chemistry·2026
Same author

Decarboxylation via a Higher Electronic Excited State Drives LSSmOrange Photoconversion.

ACS physical chemistry Au·2026
Same author

DNA-interacting lanthanide complexes with a DOTA-derived dipyrido[3,2-<i>a</i>;2',3'-<i>c</i>]phenazine ligand for near-infrared luminescence.

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

Crystal Engineering of Intrinsic Dynamicity in Metal-Organic Frameworks for Adaptive Multicomponent Catalysis.

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

Integrating Twisted and Push-Pull Structural Motifs for Efficient Dual-Functioning Near-Infrared BODIPY Photosensitizers.

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

An unusual two-dimensional MOF formed from Ni<sup>II</sup>, thio-phene-2,5-di-carboxyl-ate and <i>trans</i>-1,2-bis-(pyridin-4-yl)ethyl-ene.

Acta crystallographica. Section E, Crystallographic communications·2026

Related Experiment Video

Updated: May 9, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Diazadithia[7]helicenes: Synthetic Exploration, Solid-State Structure, and Properties.

Deepali Waghray1, Arvid Cloet, Kristof Van Hecke

  • 1Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven (Belgium), Fax: (+32) 16327990.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|July 23, 2013
PubMed
Summary

Novel diazadithia[7]helicenes were synthesized and functionalized. These conformationally stable compounds exhibit antiparallel columnar stacking and tunable electronic properties, paving the way for new materials.

Keywords:
Wittig reactionschiral resolutioncyclizationhelical structureshelicenes

More Related Videos

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Related Experiment Videos

Last Updated: May 9, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Helicenes are chiral aromatic compounds with unique three-dimensional structures.
  • Diazadithia[7]helicenes represent a specific class of helicenes with potential applications in advanced materials.

Purpose of the Study:

  • To synthesize novel diazadithia[7]helicenes.
  • To explore their functionalization and conformational stability.
  • To investigate their solid-state structure and electronic properties.

Main Methods:

  • Synthesis via Wittig reaction and photocyclization.
  • Functionalization using nucleophilic aromatic substitution and palladium-catalyzed cross-coupling reactions (Suzuki, Buchwald-Hartwig).
  • Characterization by single-crystal X-ray diffraction, racemization studies, and electrochemical/optical measurements.

Main Results:

  • Successful synthesis of diazadithia[7]helicenes from ethyl 7-chloro-8-formylthieno[3,2-f]quinoline-2-carboxylate.
  • Diverse functionalization achieved with various nucleophiles and cross-coupling reactions.
  • Enantiopure [7]helicenes demonstrated high conformational stability.
  • Crystal structures revealed antiparallel columnar stacking.
  • HOMO-LUMO gaps were determined via electrochemical and optical methods.

Conclusions:

  • The study presents a viable synthetic route to functionalized diazadithia[7]helicenes.
  • These compounds exhibit enhanced conformational stability and unique solid-state packing.
  • Their tunable electronic properties suggest potential for optoelectronic applications.