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Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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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
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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.
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[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.3K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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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.
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Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

13.8K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Photoswitchable Norbornadiene-Quadricyclane Interconversion Mediated by Covalently Linked C60.

Patrick Lorenz1, Andreas Hirsch1

  • 1Chair of Organic Chemistry II, Friedrich-Alexander Universität Erlangen-Nürnberg, Nikolaus-Fiebiger-Strasse 10, 91058, Erlangen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 28, 2019
PubMed
Summary

Researchers synthesized norbornadiene/quadricyclane (NBD/QC) fullerene hybrids. These NBD-fullerene compounds can be switched between NBD and QC forms using specific light wavelengths, creating a pure photoswitch for molecular applications.

Keywords:
energy conversionfullerenesmolecular switchesnorbornadienephotoswitch

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Norbornadiene/quadricyclane (NBD/QC) systems are known energy storage molecules.
  • Fullerenes are versatile carbon allotropes with unique electronic properties.
  • Hybrid molecules combining NBD/QC scaffolds with fullerenes offer novel functionalities.

Purpose of the Study:

  • To synthesize and characterize novel norbornadiene/quadricyclane fullerene hybrids.
  • To investigate the photoisomerization behavior of these hybrid systems.
  • To develop a light-driven molecular switch based on NBD/QC fullerene interconversion.

Main Methods:

  • Cyclopropanation of C60 using malonates with NBD scaffolds to form monoadducts and hexakisadducts.
  • Photoisomerization studies under varying UV-Vis irradiation wavelengths.
  • Redox potential measurements to study the fullerene core's influence.

Main Results:

  • Successful synthesis of a library of NBD-fullerene monoadducts and hexakisadducts.
  • Demonstration of direct photoisomerization from NBD-fullerene to QC-fullerene derivatives.
  • Achieved reversible switching between NBD and QC forms using light (310-400 nm).
  • The fullerene core's electron affinity impacts QC derivative properties.

Conclusions:

  • NBD-fullerene hybrids can be controllably switched between isomers using light, functioning as pure photoswitches.
  • The developed system simplifies the study of NBD-QC interconversion.
  • These hybrids show potential for applications in molecular switches and light-responsive materials.