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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: 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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Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

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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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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.1K
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.
Selection Rules: Photochemical Activation
2.1K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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Electroactive Polymer Nanoparticles Exhibiting Photothermal Properties
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BODIPY-Based Photoacid Generators for Light-Induced Cationic Polymerization.

Karthik Sambath1, Zhaoxiong Wan1, Qi Wang1

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

Organic Letters
|January 17, 2020
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Summary

Researchers developed novel BODIPY-based photoacid generators (PAGs) that produce protons under green and red LED light. This breakthrough enables red-light-triggered cationic polymerization, showcasing a new application for advanced PAGs.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Polymer Science

Background:

  • Photoacid generators (PAGs) are crucial for photolithography and catalysis, releasing protons (H+) upon light exposure.
  • Existing PAGs often require UV light, limiting applications in biological or transparent systems.
  • BODIPY dyes offer tunable photophysical properties, making them attractive scaffolds for novel functional materials.

Purpose of the Study:

  • To design and synthesize the first BODIPY-based photoacid generators (PAGs).
  • To achieve proton generation using visible light, specifically green and red LED irradiation.
  • To demonstrate a proof-of-concept application in red-LED-triggered cationic polymerization.

Main Methods:

  • Synthesis of novel BODIPY derivatives with donor-acceptor (D-A) and donor-π-acceptor (D-π-A) conjugation structures.
  • Photophysical characterization to determine light absorption and emission properties.
  • Evaluation of proton generation efficiency upon green and red LED irradiation.
  • Demonstration of red-LED-triggered cationic polymerization using the synthesized PAGs.

Main Results:

  • Successfully synthesized novel BODIPY-based PAGs with tailored D-A and D-π-A architectures.
  • Achieved efficient proton generation upon irradiation with green and red LED light.
  • Demonstrated the capability of red-light-absorbing PAGs to initiate cationic polymerization.
  • Established a direct correlation between red-light absorption and polymerization initiation.

Conclusions:

  • The developed BODIPY-based PAGs represent a significant advancement in visible-light-responsive photoacid generation.
  • These PAGs offer a versatile platform for applications requiring spatiotemporal control of acidity, particularly in red-light-triggered processes.
  • The successful demonstration of red-LED-initiated cationic polymerization highlights the practical potential of these novel materials.