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Solid-phase synthesis of polymers using the ring-opening metathesis polymerization.

Jason K Pontrello1, Matthew J Allen, Eric S Underbakke

  • 1Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.

Journal of the American Chemical Society
|October 20, 2005
PubMed
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A new solid-phase synthesis method enables polymer creation using ring-opening metathesis polymerization (ROMP). This technique allows for diverse polymer functionalization and efficient release from solid supports.

Area of Science:

  • Polymer Chemistry
  • Organic Synthesis
  • Materials Science

Background:

  • Solid-phase synthesis offers advantages in purification and automation.
  • Ring-opening metathesis polymerization (ROMP) is a versatile method for polymer synthesis.
  • Integrating solid-phase techniques with ROMP can streamline polymer preparation and functionalization.

Purpose of the Study:

  • To develop a general solid-phase synthesis method for polymers using ROMP.
  • To enable on-resin modification and efficient liberation of synthesized polymers.
  • To demonstrate the utility of this method for creating functional polymers.

Main Methods:

  • Solution polymerization to form block copolymers.
  • Immobilization of one block onto a resin-bound functional group.

Related Experiment Videos

  • On-resin modification of the other block.
  • Cleavage of the polymer from the resin support.

    • Main Results:

    • A block copolymer with N-hydroxysuccinimidyl ester and maleimide blocks was synthesized.
    • The Diels-Alder reaction was used for polymer immobilization and subsequent release via a reversible furan-maleimide adduct.
    • Diverse amine structures were successfully used for on-resin modification.
    • The synthesized polymers demonstrated comparable potency to solution-synthesized polymers in lectin binding assays.

    Conclusions:

    • A novel solid-phase synthesis strategy for ROMP polymers has been established.
    • The method allows for controlled functionalization and facile release of polymers.
    • This approach facilitates the rapid synthesis of diverse and functional polymers.