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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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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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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 species into...
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Anionic Chain-Growth Polymerization: Overview01:20

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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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Radical Chain-Growth Polymerization: Chain Branching01:17

Radical Chain-Growth Polymerization: Chain Branching

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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Robust Direct (Hetero)arylation Polymerization in Biphasic Conditions.

François Grenier1, Karine Goudreau1, Mario Leclerc1

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|January 27, 2017
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Direct (hetero)arylation polymerization (DHAP) was successfully performed in water/toluene biphasic conditions for the first time. This robust and scalable method yields high-quality conjugated polymers under mild, ambient pressure conditions.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Direct (hetero)arylation polymerization (DHAP) is a powerful method for synthesizing conjugated polymers.
  • Traditional DHAP often requires anhydrous conditions and specific catalysts.
  • Developing more sustainable and versatile DHAP protocols is crucial for advanced materials development.

Purpose of the Study:

  • To develop a novel biphasic water/toluene protocol for direct (hetero)arylation polymerization (DHAP).
  • To demonstrate the robustness and broad substrate scope of the new DHAP method.
  • To achieve high molecular weight conjugated polymers with excellent properties.

Main Methods:

  • Utilized a biphasic water/toluene system for DHAP.
  • Employed a single set of polymerization conditions for diverse thienyl- and phenyl-based substrates.
  • Characterized the resulting polymers using differential scanning calorimetry, 1H NMR, and UV-vis-NIR spectroscopy.

Main Results:

  • Achieved the first synthesis of conjugated polymers via DHAP in biphasic water/toluene.
  • Demonstrated high robustness, tolerating air introduction during polymerization.
  • Obtained high molecular weight polymers with properties comparable or superior to existing methods.
  • Showcased versatility with both electron-rich and electron-poor substrates.

Conclusions:

  • The developed biphasic DHAP protocol is efficient, versatile, and scalable.
  • This method offers a sustainable and cost-effective approach using "wet" reagents at ambient pressure.
  • The protocol provides a new avenue for synthesizing high-performance conjugated polymers.