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Related Concept Videos

Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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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

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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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Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Step-Growth Polymerization: Overview01:03

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Step-growth or condensation polymerization is a stepwise reaction of bi or multifunctional monomers to form long-chain polymers. As all the monomers are reactive, most of the monomers are consumed at the early stages of the reaction to form small chains of reactive oligomers, which then combine to form long polymer chains in the late stages. Hence, the reaction has to proceed for a long time to achieve high molecular weight polymers.
Many natural and synthetic polymers are produced by...
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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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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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Microwave-assisted Functionalization of Polyethylene glycol and On-resin Peptides for Use in Chain Polymerizations and Hydrogel Formation
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Accelerated Post-Polymerization Amidation of Polymers with Side-Chain Ester Groups by Intramolecular Activation.

Joachim F R Van Guyse1,2, Meike N Leiske1, Jente Verjans1

  • 1Supramolecular Chemistry Group, Centre of Macromolecular Chemistry (CMaC), Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 S4, 9000, Ghent, Belgium.

Angewandte Chemie (International Ed. in English)
|May 4, 2022
PubMed
Summary

This study accelerates polymer amidation using functionalized amines, enabling efficient synthesis of amide-containing polymers. The method enhances polymer upcycling and diversification through faster catalytic conversion of esters to amides.

Keywords:
AminesCatalysisEstersPolymersPost-Polymerization Modification

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Esters are common in polymers, but their direct catalytic conversion to amides is slow.
  • Understanding how polymer structure affects amidation reactivity is crucial for polymer modification.
  • Existing methods face challenges with reaction kinetics and structural influences.

Purpose of the Study:

  • To develop an accelerated method for the catalytic conversion of esters to amides in polymers.
  • To investigate the role of amine structure in facilitating polymer amidation.
  • To elucidate the influence of polymer architecture on amidation efficiency.

Main Methods:

  • Utilized amines with hydrogen bond donating or accepting groups for accelerated amidation.
  • Investigated reactivity differences between polymers with pendant ester groups versus main-chain esters.
  • Employed FT-IR spectroscopy and molecular mechanics modeling to confirm reaction mechanisms.

Main Results:

  • Achieved a >400-fold increase in reactivity for polymers with pendant ester groups compared to main-chain esters.
  • Demonstrated accelerated (co)amidation of polymers using specifically designed amines.
  • Observed a positive correlation between reactivity and degree of polymerization for poly(methyl acrylate).

Conclusions:

  • Hydrogen-bond mediated intramolecular activation of esters enhances amidation rates.
  • The developed method allows for the synthesis of diverse (co)polymers with amide side chains.
  • This approach offers a pathway for efficient polymer diversification and upcycling from accessible precursors.