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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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Radical Chain-Growth Polymerization: Overview01:10

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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Step-Growth Polymerization: Overview01:03

Step-Growth Polymerization: Overview

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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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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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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Novel BODIPY-Based Photobase Generators for Photoinduced Polymerization.

Shupei Yu1, Ojasvita Reddy1, Alperen Abaci2

  • 1. . Department of Chemistry and Environmental Science, College of Science and Liberal Arts, New Jersey Institute of Technology, 323 Martin Luther King Jr. Blvd., Newark, New Jersey 07102, United States.

ACS Applied Materials & Interfaces
|September 14, 2023
PubMed
Summary
This summary is machine-generated.

New BODIPY-based photobase generators (PBGs) efficiently release strong bases under visible light. These novel PBGs enable efficient visible-light-triggered polymerization for advanced material applications.

Keywords:
BODIPYLED lightphotobase generatorphotopolymerizationthiol−ene Michael reaction

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Area of Science:

  • Organic Chemistry
  • Polymer Science
  • Photochemistry

Background:

  • Photobase generators (PBGs) offer spatiotemporal control of base release for initiating polymerization.
  • Existing PBGs have limitations including short absorption wavelengths and inefficient base release, hindering photopolymerization efficiency.
  • There is a need for visible-light-triggered PBGs capable of releasing strong bases efficiently.

Purpose of the Study:

  • To develop novel BODIPY-based visible-light-sensitive photobase generators (PBGs).
  • To enable efficient light-induced activation of thiol-ene Michael addition reactions and polymerization.
  • To improve the efficiency of base release and polymerization rates using the heavy atom effect.

Main Methods:

  • Design and synthesis of two novel BODIPY-based PBGs.
  • Conjugation of BODIPY light-sensitive protecting groups with tetramethylguanidine (TMG), a strong base.
  • Exploitation of the heavy atom effect to enhance TMG release and polymerization kinetics.

Main Results:

  • The novel BODIPY-based PBGs demonstrate efficient visible-light-triggered release of TMG.
  • These PBGs exhibit extraordinary activity in thiol-ene Michael addition-based polymerization.
  • Successful application in surface coating and polymer network formation with various thiol and vinyl monomers.

Conclusions:

  • The developed BODIPY-based PBGs are highly effective visible-light-sensitive initiators for anionic polymerization.
  • The heavy atom effect significantly enhances the efficiency of base release and polymerization.
  • These PBGs offer a promising platform for advanced photopolymerization applications, including surface modification and material fabrication.