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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...
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Structure and Physical Properties of Alkynes02:37

Structure and Physical Properties of Alkynes

Introduction:
In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose molecules contain saturated single bonds (i.e., alkanes) or unsaturated double or triple bonds. Alkenes contain carbon–carbon double bonds and have a structural formula CnH2n. Unsaturated hydrocarbons containing carbon–carbon triple bonds are called "alkynes" and are structurally represented by the formula CnH2n-2.
The simplest alkyne is ethyne, or...
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.
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.
UV–Vis Spectroscopy: Woodward–Fieser Rules01:29

UV–Vis Spectroscopy: Woodward–Fieser Rules

UV–Visible absorption spectra of conjugated dienes arise from the lowest energy π → π* transitions. The light-absorbing part of the molecule is called the chromophore, and the substituents directly attached to the chromophore are called auxochromes. A strong correlation exists between the absorption maxima, λmax, and the structure of a conjugated π system. The Woodward–Fieser rules predict the value of λmax for a given structure by adding the contributions...

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Related Experiment Video

Updated: Jul 3, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Multiethynyl corannulenes: synthesis, structure, and properties.

Yao-Ting Wu1, Davide Bandera, Roman Maag

  • 1Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland.

Journal of the American Chemical Society
|July 23, 2008
PubMed
Summary

Syntheses of ethynyl-substituted corannulenes were achieved using Sonogashira and modified Nolan reactions. These compounds exhibit unique columnar structures and tunable luminescence properties dependent on substitution.

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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

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Last Updated: Jul 3, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
09:35

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions
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1,3,5-Triphenylbenzene and Corannulene as Electron Receptors for Lithium Solvated Electron Solutions

Published on: October 10, 2016

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Corannulenes are polycyclic aromatic hydrocarbons with unique bowl-shaped structures.
  • Ethynyl-substituted corannulenes offer potential for novel electronic and optical applications.

Purpose of the Study:

  • To synthesize and characterize a series of ethynyl-substituted corannulenes.
  • To investigate their crystal structures, molecular packing, and photophysical properties.

Main Methods:

  • Sonogashira cross-coupling reaction for di- and tetra-substituted corannulenes.
  • Modified Nolan procedure for penta-substituted corannulenes.
  • X-ray crystallography and ab initio density functional theory (DFT) computations.

Main Results:

  • Successful synthesis of ethynyl-substituted corannulenes (classes 3, 4, and 5) in high yields.
  • Observation of polar and opposing columnar structures in crystal packing, influenced by substitution.
  • Correlation between the number of alkynyl arms and increased corannulene bowl depth.
  • High-quantum-efficiency solution luminescence with tunable emission wavelengths.

Conclusions:

  • Ethynyl substitution provides a versatile route to functionalized corannulenes with controllable self-assembly and photophysical behavior.
  • The structural and electronic properties can be tuned by varying the number and type of ethynyl substituents.
  • These findings open avenues for designing advanced materials with tailored optical and electronic characteristics.