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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...
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Olefin Metathesis Polymerization: Overview01:13

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists...
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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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Cationic Chain-Growth Polymerization: Mechanism00:57

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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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Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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Metathesis Cascade-Triggered Depolymerization of Enyne Self-Immolative Polymers*.

Jingsong Yuan1, Gavin J Giardino1, Jia Niu1

  • 1Department of Chemistry, Boston College, Chestnut Hill, MA, 02467, USA.

Angewandte Chemie (International Ed. in English)
|August 28, 2021
PubMed
Summary
This summary is machine-generated.

Novel enyne self-immolative polymers (SIPs) depolymerize completely upon triggering with a metathesis catalyst. These stable polymers show potential as advanced stimuli-responsive materials for diverse applications.

Keywords:
cascade reactionsdepolymerizationenyne metathesisself-immolative polymersstimuli-responsive materials

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Self-immolative polymers (SIPs) offer controlled degradation pathways.
  • Metathesis reactions are powerful tools for polymer modification and synthesis.
  • Developing robust SIPs with tunable depolymerization is crucial for advanced materials.

Purpose of the Study:

  • To report a novel class of enyne self-immolative polymers (SIPs).
  • To investigate the metathesis cascade-triggered depolymerization of these SIPs.
  • To establish the potential of these polymers as stimuli-responsive materials.

Main Methods:

  • Synthesis of SIPs using polycondensation and iterative exponential growth.
  • Evaluation of 1,6-enyne structures for efficient metathesis cascade reactions.
  • Characterization of polymer stability under various conditions (acid, base, nucleophiles, heat).

Main Results:

  • Optimized 1,6-enyne structures enable efficient metathesis cascade reactions.
  • Synthesized SIPs exhibit excellent stability against harsh chemical and thermal conditions.
  • Complete and efficient depolymerization is achieved upon triggering with a metathesis catalyst.
  • Incorporation of a terminal alkene enhances depolymerization efficiency.

Conclusions:

  • A new class of enyne SIPs responsive to metathesis catalysts has been developed.
  • These SIPs demonstrate high stability and controlled depolymerization.
  • The findings highlight the potential of enyne SIPs as stimuli-responsive materials.