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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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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...
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Cationic Chain-Growth Polymerization: Mechanism00:57

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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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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

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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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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

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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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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Fluorogenic monomer activation for protein-initiated atom transfer radical polymerization.

Danyal Tahseen1, Jemima R Sackey-Addo1, Zachary T Allen1

  • 1Department of Chemistry, Trinity University, 1 Trinity Place, San Antonio, TX 78212, USA. ccooley@trinity.edu.

Organic & Biomolecular Chemistry
|June 13, 2022
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Fluorogenic atom transfer radical polymerization (ATRP) enables real-time detection of polymer formation. This study advances fluorogenic ATRP for bioorthogonal applications, initiating polymerization from protein surfaces with fluorescence activation.

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Area of Science:

  • Polymer Chemistry
  • Bioconjugation
  • Fluorescence Spectroscopy

Background:

  • Fluorogenic atom transfer radical polymerization (ATRP) offers real-time detection of polymer formation via fluorescence.
  • Advancing this technique for biodetection requires understanding probe activation mechanisms and initiating polymerization from biomolecules.

Purpose of the Study:

  • To elucidate the mechanism of fluorogenic probe fluorescence activation.
  • To demonstrate bioorthogonal, protein-initiated fluorogenic ATRP for biomolecular applications.

Main Methods:

  • Monomer hydrogenation to investigate probe fluorescence.
  • Surface conjugation of proteins with initiators for ATRP.
  • Real-time fluorescence monitoring of polymerization from protein surfaces.
  • Assessing assay performance in complex biological media.

Main Results:

  • Monomer hydrogenation confirmed covalent enone attachment is key to probe quenching and fluorescence activation.
  • Successful initiation of fluorogenic ATRP from bovine serum albumin (BSA) conjugates was achieved.
  • Negligible background fluorescence was observed from unmodified BSA controls.
  • Polymer formation was visualized in real-time in complex biological environments.

Conclusions:

  • Aqueous fluorogenic ATRP is a robust, bioorthogonal method for biomolecular-initiated polymerization.
  • Real-time fluorescence activation provides a sensitive detection mechanism.
  • This technique holds potential for advanced biodetection and biomolecular analysis.