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Iodosylbenzene-Pseudohalide-Based Initiators for Radical Polymerization.

Rajesh Kumar1, Yakun Cao1, Nicolay V Tsarevsky1

  • 1Department of Chemistry, Southern Methodist University , 3215 Daniel Avenue, Dallas, Texas 75275, United States.

The Journal of Organic Chemistry
|October 4, 2017
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Summary

Iodosylbenzene generates hypervalent iodine(III) compounds that initiate polymerization of various monomers. These polymers contain (pseudo)halide end-groups, enabling further functionalization via click chemistry or reactions with diamines.

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Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Hypervalent Iodine Chemistry

Background:

  • Hypervalent iodine compounds offer unique reactivity.
  • Radical polymerization is a cornerstone of polymer synthesis.
  • Controlled polymer functionalization is crucial for advanced materials.

Purpose of the Study:

  • To investigate the polymerization initiation using hypervalent iodine(III) compounds.
  • To explore the incorporation of (pseudo)halide functionalities into polymer chains.
  • To demonstrate post-polymerization modification of functionalized polymers.

Main Methods:

  • Reaction of iodosylbenzene with various (pseudo)halides to form hypervalent iodine(III) intermediates.
  • Initiation of free-radical polymerization of styrene, (meth)acrylates, and vinyl esters.
  • Characterization of resulting polymers using elemental analysis, IR, and NMR spectroscopy.
  • Post-polymerization modification via click chemistry and reactions with diamines.

Main Results:

  • Unstable hypervalent iodine(III) compounds, PhIX2, were generated and initiated polymerization.
  • Polymers with (pseudo)halide functionalities at α- and potentially ω-chain ends were synthesized.
  • Dead-end polymerization occurred with rapidly generated initiators and slowly polymerizing monomers.
  • Continuous initiator generation led to higher conversions and molecular weights.
  • Azide- and isocyanate-functionalized polymers were successfully modified into triazole- and urea-linked polymers.

Conclusions:

  • Iodosylbenzene-derived hypervalent iodine(III) compounds are effective radical initiators.
  • Polymer end-group functionalization with (pseudo)halides is achievable.
  • Controlled polymerization conditions influence conversion and molecular weight.
  • Functionalized polymers can be further modified to create advanced polymer architectures.