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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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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

Los corannulenos multietinile: síntesis, estructura y propiedades.

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
Resumen

Las síntesis de corannulenes sustituidos por etinil se lograron utilizando Sonogashira y reacciones Nolan modificadas. Estos compuestos exhiben estructuras columnares únicas y propiedades de luminiscencia sintonizables dependientes de la sustitución.

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

Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Ciencia de los materiales Ciencia de los materiales.
  • Química supramolecular de las moléculas.

Sus antecedentes:

  • Los corannulenes son hidrocarburos aromáticos policíclicos con estructuras únicas en forma de cuenco.
  • Los corannulenes sustituidos por etinile ofrecen potencial para nuevas aplicaciones electrónicas y ópticas.

Objetivo del estudio:

  • Para sintetizar y caracterizar una serie de corannulenes sustituidos por etinil.
  • Para investigar sus estructuras cristalinas, empaque molecular y propiedades fotofísicas.

Principales métodos:

  • Reacción de acoplamiento cruzado de Sonogashira para corannulenes di- y tetrasubstituidos.
  • Procedimiento Nolan modificado para corannulenes penta-sustituidos.
  • Cristalografía de rayos X y ab initio cálculos de la teoría funcional de la densidad (DFT).

Principales resultados:

  • Síntesis exitosa de corannulenes sustituidos por etinil (clases 3, 4 y 5) en altos rendimientos.
  • Observación de estructuras columnares polares y opuestas en el empaque de cristales, influenciadas por la sustitución.
  • Correlación entre el número de brazos de alquinyl y el aumento de la profundidad del cuenco de corannulene.
  • Luminiscencia de solución de alta eficiencia cuántica con longitudes de onda de emisión sintonizables.

Conclusiones:

  • La sustitución de etinyl proporciona una ruta versátil para corannulenes funcionalizados con autoensamblaje controlable y comportamiento fotofísico.
  • Las propiedades estructurales y electrónicas se pueden ajustar variando el número y el tipo de sustituyentes de etinyl.
  • Estos hallazgos abren caminos para diseñar materiales avanzados con características ópticas y electrónicas a medida.