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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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
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.
2.9K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.4K
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.
2.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.0K
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.
12.0K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

5.0K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable,...
5.0K

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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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All-Visible-Light-Activated Dithienylethenes Induced by Intramolecular Proton Transfer.

Hancheng Xi1, Zhipeng Zhang1, Weiwei Zhang1

  • 1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Shanghai Key Laboratory of Functional Materials Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering , East China University of Science & Technology , Shanghai 200237 , China.

Journal of the American Chemical Society
|October 29, 2019
PubMed
Summary
This summary is machine-generated.

Researchers developed novel dithienylethenes (DTEs) that switch using only visible light, avoiding harmful ultraviolet radiation. This breakthrough utilizes an intramolecular proton transfer (IPT) process for efficient and reversible photochromic applications.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Dithienylethenes (DTEs) are known for light-responsive photochromism, thermal stability, and fatigue resistance.
  • Existing DTE systems often require high-energy ultraviolet (UV) light for photocyclization, posing safety concerns.
  • Developing visible-light-activated DTEs is crucial for broader, safer applications.

Purpose of the Study:

  • To design and synthesize novel DTEs capable of all-visible-light-driven photochromism.
  • To investigate the mechanism enabling visible-light activation in DTEs.
  • To establish a general platform for creating safe, visible-light-responsive photochromic materials.

Main Methods:

  • Rational design of DTEs incorporating an intramolecular proton transfer (IPT) functional group.
  • Spectroscopic analysis to characterize absorption properties and photochromic behavior.
  • Evaluation of photoswitching efficiency in polar solvents and polymeric gel systems.

Main Results:

  • Successfully designed DTEs with an additional red-shifted absorption band due to IPT.
  • Demonstrated efficient photocyclization of DTEs using visible light (450 nm).
  • Achieved excellent reversible photoswitching performance in both solution and gel states, avoiding UV light.

Conclusions:

  • The IPT process provides a viable strategy for creating all-visible-light-driven DTEs.
  • These novel DTEs offer a safe and efficient alternative to UV-activated systems.
  • The developed platform enables broad applicability in various photochromic systems, particularly in polymeric gels.