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Related Concept Videos

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

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

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...
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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 of a...
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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...
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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 generated carbocation,...
Anionic Chain-Growth Polymerization: Overview01:20

Anionic Chain-Growth Polymerization: Overview

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,...
Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

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 acceptor.

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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers
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Depolymerizable Olefinic Polymers Based on Fused-Ring Cyclooctene Monomers

Published on: December 16, 2022

Acidic polysaccharide mimics via ring-opening metathesis polymerization.

Michel Wathier1, Stephanie S Stoddart, Matthew J Sheehy

  • 1Department of Biomedical Engineering, Metcalf Center for Science and Engineering, Boston University, Boston, Massachusetts 02215, United States.

Journal of the American Chemical Society
|October 23, 2010
PubMed
Summary

Researchers developed a new method to create high-molecular-weight hydrophilic polymers with carboxylic acid and hydroxyl groups. These carbohydrate-like polymers show promise as synthetic polysaccharide substitutes in biotech and pharma.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Biotechnology

Background:

  • Hydrophilic polymers with diverse functional groups are crucial for biomedical applications.
  • Mimicking natural polysaccharides like alginate is a key goal in synthetic polymer design.

Purpose of the Study:

  • To develop an efficient and general synthetic strategy for high-molecular-weight hydrophilic polymers.
  • To create polymers with both carboxylic acid and hydroxyl pendant groups.
  • To explore applications as synthetic polysaccharide substitutes.

Main Methods:

  • Ring-opening metathesis polymerization (ROMP) of methyl 5-oxanorbornene-2-carboxylate using Grubbs catalyst II.
  • Post-polymerization modification to introduce hydroxyl or carboxylic acid functionalities.
  • Characterization of polymer molecular weight (∼100,000 to 5,000,000 g/mol).

Main Results:

  • Successfully synthesized poly(5,6-dihydroxyoxanorbornane carboxylic acid) with high molecular weights.
  • Demonstrated tuning of hydrophobic/hydrophilic properties through functional group introduction.
  • Formation of hydrogels with polylysine, mimicking alginate behavior.

Conclusions:

  • The described synthetic strategy is efficient and general for producing functional hydrophilic polymers.
  • These carbohydrate-like polymers are valuable for structure-property relationship studies.
  • The polymers offer potential as novel synthetic polysaccharide substitutes in biotechnology and pharmaceuticals.