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Related Concept Videos

Catalysis02:50

Catalysis

27.2K
The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
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
1.9K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.4K
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.
2.4K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.1K
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.
2.1K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.9K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.9K

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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Stimuli-Responsive Catenane-Based Catalysts.

Adrien Bessaguet1, Quentin Blancart-Remaury1, Pauline Poinot1

  • 1University of Poitiers, UMR CNRS 7285, Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), 4 rue Michel-Brunet, TSA 51106, 86073, Poitiers cedex 9, France.

Angewandte Chemie (International Ed. in English)
|December 8, 2022
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Summary
This summary is machine-generated.

Stimuli-responsive [2]catenanes act as OFF/ON catalysts for the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. Breaking the mechanical bond releases the encapsulated copper(I) ion, restoring catalytic activity for triazole formation.

Keywords:
CatenaneClick ChemistryOff/on CatalystsSelf-Immolative LinkerSignal Amplification

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Area of Science:

  • Supramolecular Chemistry
  • Catalysis

Background:

  • Rotaxanes and molecular knots possess unique properties due to permanent mechanical bonds.
  • Disassembly of interlocked architectures can unlock masked properties.

Purpose of the Study:

  • To develop stimuli-responsive catalysts using copper(I)-complexed [2]catenanes.
  • To create OFF/ON catalytic systems for the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction.

Main Methods:

  • Synthesis of stimuli-responsive Cu(I)-complexed [2]catenanes.
  • Investigation of catalytic activity in the CuAAC reaction.
  • Controlled disassembly of the [2]catenane structure.

Main Results:

  • Encapsulation of Cu(I) within [2]catenanes rendered it catalytically inactive for CuAAC.
  • Controlled opening of the macrocycles broke the mechanical bond.
  • Disassembly restored the catalytic activity of the Cu(I) ion.

Conclusions:

  • Developed OFF/ON catalysts based on stimuli-responsive [2]catenanes.
  • Demonstrated controlled activation of catalysis through mechanical bond disruption.
  • Highlighted potential for signal amplification in various applications.