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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.6K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.4K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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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
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.0K
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

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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

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Electrocatalytic Depolymerization of Self-Immolative Poly(Dithiothreitol) Derivatives.

Magnus Hansen-Felby1, Steen U Pedersen1, Kim Daasbjerg1,2

  • 1Department of Chemistry and Interdiciplinary Nanoscience Center (iNANO), Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark.

Molecules (Basel, Switzerland)
|October 14, 2022
PubMed
Summary
This summary is machine-generated.

Electrogenerated anthraquinone radical anion (AQ•-) efficiently triggers catalytic depolymerization of poly(dithiothreitol) (pDTT) polymers. This electron-transfer method offers a general approach for degrading disulfide-containing polymers.

Keywords:
anthraquinonedepolymerizationdisulfideelectrocatalyticpoly(dithiothreitol)polymerradical anionself-immolative

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Area of Science:

  • Polymer Chemistry
  • Electrochemistry
  • Materials Science

Background:

  • Self-immolative polymers (SIPs) offer controlled degradation pathways.
  • Poly(dithiothreitol) (pDTT) is a class of SIPs featuring disulfide bonds in their backbone and end-caps.
  • Initiating depolymerization of pDTT typically requires specific triggers.

Purpose of the Study:

  • To investigate the use of electrogenerated anthraquinone radical anion (AQ•-) as a trigger for pDTT depolymerization.
  • To determine the efficiency and mechanism of AQ•--mediated depolymerization.
  • To assess the general applicability of this electrochemical method for disulfide polymers.

Main Methods:

  • Synthesis of pDTT derivatives with varying end-caps (thiohexyl, AQ, methyl).
  • Electrochemical generation of anthraquinone radical anion (AQ•-).
  • Monitoring depolymerization kinetics using electrochemical and analytical techniques.

Main Results:

  • AQ•- effectively catalyzed the rapid depolymerization of all studied pDTT derivatives.
  • Complete depolymerization of pDTT was achieved with as little as 0.2 electrons per polymer chain.
  • A mechanism involving electron transfer to disulfide bonds, generating thiyl radicals, was proposed.
  • Thiyl radicals propagate depolymerization via a chain reaction.

Conclusions:

  • Electrochemical triggering using AQ•- is a highly efficient method for initiating pDTT depolymerization.
  • This approach demonstrates a general strategy for the catalytic degradation of disulfide-containing polymers.
  • The findings open avenues for controlled polymer degradation using electrochemistry.