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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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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Polymers

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The word polymer is derived from the Greek words “poly” which means “many” and “mer” which means “parts”. Polymers are long chains of molecules composed of repeating units of smaller molecules, known as monomers. They either occur naturally, such as DNA and proteins, or can be constructed synthetically, like plastics. They have varied structural characteristics, such as linear chains, branched chains, or complex networks, that contribute to 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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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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Copolymers are the products obtained from the polymerization of multiple monomer species. So, in a polymer chain itself, there can be multiple repeating units that come from different monomers. The process of synthesizing a polymer from different monomer species is called copolymerization. When two monomers are involved, the polymer is known as a bipolymer. Polymers with three and four monomers are termed terpolymers and quaterpolymers, respectively. Figure 1 depicts the copolymerization of...
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Orthogonal and Multiresponsive Quinolinone Systems for Reversible and Recyclable Polymer Networks.

Claas-Hendrik Stamp1, Annalena Groß2, Aitana Beato Irulegui1

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Quinolinones enable controlled covalent bond switching using light and heat. This breakthrough allows for highly efficient material recycling and reuse, demonstrating a new platform for sustainable, stimuli-responsive systems.

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Area of Science:

  • Materials Science
  • Polymer Chemistry
  • Organic Chemistry

Background:

  • Precise control over covalent bond formation and cleavage is essential for advanced material recycling and reuse.
  • Reversible covalent bond manipulation is key to developing sustainable materials.
  • Thermal reversion of photochemically formed bonds is an underexplored area.

Purpose of the Study:

  • To introduce quinolinones as versatile, multistimuli-responsive motifs for controlled covalent bond manipulation.
  • To explore the thermal cleavage of quinolinone-based bonds for material deconstruction.
  • To demonstrate the application of quinolinones in recyclable polymers and coatings.

Main Methods:

  • Utilizing reversible [2π + 2π] cycloaddition reactions triggered by light and thermal stimuli.
  • Investigating the photochemical formation and thermal cleavage of quinolinone bonds.
  • Incorporating quinolinones into linear polymers for network formation and deconstruction.

Main Results:

  • Quinolinones exhibit efficient, symmetrical thermal cleavage in the solid state, achieving over 99% monomer recovery.
  • Demonstrated quantitative cyclability of at least three bond formation and cleavage cycles at the molecular level.
  • Developed phototriggered polymer networks with thermally induced bulk deconstruction, showcasing recyclability.
  • Applied quinolinones to coatings with reversible debonding and thermal degradation capabilities.

Conclusions:

  • Quinolinones provide a robust platform for stimuli-responsive materials.
  • This work establishes a new approach for designing next-generation recyclable systems.
  • The multiresponsive nature of quinolinones enhances material functionality and sustainability.