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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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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.
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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Preparation of 1° Amines: Gabriel Synthesis01:28

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Activated Phenyl Ester Vitrimers.

Stéphanie Engelen1, Bram Daelman1, Johan M Winne1

  • 1Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Krijgslaan 281-S4, Ghent, 9000, Belgium.

Macromolecular Rapid Communications
|November 13, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a novel strategy for creating adaptable polymer networks using partly aromatic esters. These dynamic cross-links enable thermal reprocessing of thermosets, offering enhanced material properties and processability.

Keywords:
phenyl estersphenylogous anhydridesvitrimers

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Aromatic esters are key motifs for thermally reprocessing thermosetting polymers.
  • All-aromatic esters have limited use in covalent adaptable networks (CAN) due to high glass transition temperatures and specific curing requirements.

Purpose of the Study:

  • To develop a strategy for incorporating partly aromatic esters as dynamic cross-links in low glass transition temperature thermosetting formulations.
  • To investigate the use of aliphatic esters derived from para-hydroxybenzoic acid as activated phenols or reactive phenylogous anhydrides.

Main Methods:

  • A small molecule study demonstrated catalyst-free acyl transfer reactions of activated phenyl ester bonds with free phenol moieties at 200°C.
  • Robust and hydrophobic polymer networks were synthesized via rapid thiol-ene UV-curing of unsaturated phenol esters.

Main Results:

  • Activated phenyl ester bonds readily exchange with free phenol moieties, with faster exchange observed in the presence of a catalyst.
  • The resulting polymer networks exhibit high thermal stability (350°C), rapid processability, and good water resistance.
  • The networks demonstrated low creep up to 120°C, indicating promising performance for CAN applications.

Conclusions:

  • Partly aromatic esters can be effectively integrated as dynamic cross-links in low glass transition temperature thermosets.
  • The developed materials offer a versatile platform for covalent adaptable networks with desirable properties.
  • This approach facilitates the design of processable, robust, and recyclable thermosetting polymers.