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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...
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.
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
UV–Vis Spectroscopy of Conjugated Systems01:32

UV–Vis Spectroscopy of Conjugated Systems

Organic compounds with conjugated double bonds show strong absorption features in the UV–visible region of the electromagnetic spectrum attributed to π → π* electronic excitations. Generally, a UV–vis absorption spectrum is recorded as a plot of absorbance vs wavelength. The wavelength of maximum absorbance, which manifests as a peak in the absorption spectrum, is denoted as λmax.
One of the factors influencing λmax is the extent of conjugation in the...
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
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...

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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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Dihydroazulene-buckminsterfullerene conjugates.

Marco Santella1, Virginia Mazzanti, Martyn Jevric

  • 1Department of Chemistry and Nano-Science Center, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark.

The Journal of Organic Chemistry
|September 19, 2012
PubMed
Summary

Buckminsterfullerene (C(60)) attachment quenches the dihydroazulene (DHA)/vinylheptafulvene (VHF) molecular switch. This C(60) quenching effect on the photo/thermoswitch depends on the distance between the molecular wire and the DHA unit.

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Area of Science:

  • Molecular electronics
  • Organic chemistry
  • Supramolecular chemistry

Background:

  • The dihydroazulene (DHA)/vinylheptafulvene (VHF) system is a photo/thermoswitch with potential in molecular electronics.
  • Buckminsterfullerene (C(60)) is a key anchoring group for attaching molecular wires to electrodes.

Purpose of the Study:

  • To investigate the influence of C(60) on the DHA-VHF switching mechanism.
  • To develop synthetic routes for covalently linked DHA-C(60) conjugates.

Main Methods:

  • Utilized Prato, Sonogashira, Hay, and Cadiot-Chodkiewicz reactions for synthesis.
  • Employed oligo(phenyleneethynylene) (OPE2 and OPE3) linkers of varying lengths.
  • Studied the light-induced ring-opening reaction of DHA to VHF.

Main Results:

  • Developed efficient synthetic protocols for DHA-C(60) conjugates.
  • Demonstrated that the distance between DHA and C(60) significantly affects the switching efficiency.
  • Observed significant quenching of the DHA to VHF conversion by C(60) when positioned closely.

Conclusions:

  • C(60) acts as a quencher for the DHA-VHF photo/thermoswitch.
  • The distance-dependent quenching highlights the potential for tuning molecular switch behavior.
  • The developed synthetic methods provide valuable building blocks for molecular electronics.