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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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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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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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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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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
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Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst
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Visible Light-Induced Cationic Polymerization Using Fullerenes.

Gorkem Yilmaz1, Birol Iskin1, Faruk Yilmaz2

  • 1Department of Chemistry, Istanbul Technical University, 34469 Maslak, Istanbul, Turkey.

ACS Macro Letters
|May 24, 2022
PubMed
Summary
This summary is machine-generated.

This study introduces a new visible light photoinitiator system for cationic polymerization using fullerene derivatives. It enables efficient polymerization of various monomers at room temperature with visible light irradiation.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Photochemistry

Background:

  • Cationic polymerization is a crucial process for synthesizing polymers.
  • Visible light-initiated polymerization offers advantages in control and safety.
  • Fullerene derivatives have shown potential in photochemistry and materials applications.

Purpose of the Study:

  • To develop a novel visible light-sensitive photoinitiator system for cationic polymerization.
  • To investigate the use of fullerene derivatives (C60 and polystyrene-C60 adduct) in initiating polymerization.
  • To explore the mechanism of photoinitiation under visible light.

Main Methods:

  • Visible light irradiation (λ > 400 nm) of monomers in the presence of fullerene derivatives and oxidizing salts.
  • Utilizing monomers such as cyclohexene oxide, iso-butyl vinyl ether, and N-vinylcarbazole.
  • Investigating polymerization in bulk and chlorobenzene solutions.
  • Correlating polymerization with optical absorption, free energy changes (ΔG), and proton scavenging studies.

Main Results:

  • Successful initiation of cationic polymerization of various monomers using visible light.
  • Demonstrated effectiveness of both bare C60 and polystyrene-C60 adduct as photoinitiators.
  • Identified a mechanism involving exciplex formation, electron transfer, and generation of radical cations and Brønsted acid.

Conclusions:

  • The developed photoinitiator system is efficient for visible light-induced cationic polymerization.
  • Fullerene derivatives, in conjunction with oxidizing salts, provide a versatile platform for photoinitiation.
  • The proposed mechanism provides insight into the radical cation and Brønsted acid-mediated polymerization process.