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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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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 species into the...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Radical polymerization initiated by Bergman cyclization.

Joseph D Rule1, Scott R Wilson, Jeffrey S Moore

  • 1Department of Chemistry and School of Chemical Sciences, University of Illinois, Urbana, IL 61801, USA.

Journal of the American Chemical Society
|October 23, 2003
PubMed
Summary
This summary is machine-generated.

A novel diradical initiator, generated via Bergman cyclization, efficiently starts radical polymerization. High molecular weight polymers are formed primarily through monoradical growth, with chain transfer agents enhancing polymerization rates.

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Area of Science:

  • Polymer Chemistry
  • Organic Chemistry
  • Radical Polymerization

Background:

  • Diradicals are reactive intermediates with potential applications in initiating polymerization.
  • The Bergman cyclization is a known method for generating diradicals from enediynes.
  • Understanding diradical behavior in polymerization is crucial for controlling polymer properties.

Purpose of the Study:

  • To investigate the use of a Bergman cyclization-derived diradical as an initiator for radical polymerization.
  • To determine the polymerization mechanism and efficiency with various monomers.
  • To elucidate the role of chain transfer and intramolecular termination in diradical-initiated polymerizations.

Main Methods:

  • Synthesis of 3,4-benzocyclodec-3-ene-1,5-diyne and its Bergman cyclization to generate the diradical.
  • Radical polymerization experiments with various monomers (e.g., methacrylates, acrylonitrile).
  • Analysis of polymer molecular weight, polymerization rates, and identification of small molecule byproducts.

Main Results:

  • The diradical efficiently initiated polymerization, particularly for methacrylates, yielding high molecular weight polymers.
  • Polymer propagation primarily occurred via a monoradical mechanism, supported by polymerization rate and degree of polymerization data.
  • Addition of chain transfer agents significantly increased the polymerization rate of acrylonitrile (>20-fold).
  • Small molecule products consistent with diradical intramolecular termination were identified.

Conclusions:

  • The Bergman cyclization-derived diradical is an effective initiator for radical polymerization.
  • High polymer formation proceeds through monoradical growth, often following chain transfer, due to rapid intramolecular termination of diradical chains.
  • The study provides insights into diradical self-termination pathways and the influence of chain transfer agents on polymerization kinetics.