Synthesis and postpolymerization functionalization of poly(5-iodo-1,2,3- triazole)s

Erik Schwartz, Kurt Breitenkamp, Valery V. Fokin

Research output: Contribution to journalArticle

52 Citations (Scopus)

Abstract

The step-growth, click polymerization of complementary azide and alkyne-containing monomers to produce polytriazoles (PTAs) has become a versatile and popular method of preparing structurally diverse high molecular weight polymers with a variety of useful functions. We describe here a new class of PTAs that contain 5-iodotriazole linkages prepared by the iodoalkyne version of the copper-catalyzed azide-alkyne cycloaddition (iCuAAC) of an α-azido-ω-iodoalkyne (A-B) monomer. We found this monomer to be highly reactive in the iCuAAC polymerization and show that the resulting poly(5-iodo-1,2,3-triazole) (iodo-PTA) can serve as a useful building block for further postpolymerization derivatization using palladium-catalyzed cross-couplings such as Suzuki and Heck reactions. The parent iodo-PTA and functionalized materials were successfully characterized by various spectroscopic techniques and shown to exhibit a wide range of chemical and thermal properties that are determined by the nature of functionalization at the 5-position of the triazole ring. This data suggests a certain tunability of PTA properties and offers potential for the development of a multitude of useful triazole-based materials based on this postpolymerization functionalization strategy.

Original languageEnglish
Pages (from-to)4735-4741
Number of pages7
JournalMacromolecules
Volume44
Issue number12
DOIs
Publication statusPublished - 28 Jun 2011
Externally publishedYes

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Triazoles
Alkynes
Azides
Monomers
Polymerization
Cycloaddition
Palladium
Chemical properties
Copper
Polymers
Thermodynamic properties
Molecular weight
5-iodo-1,2,3-triazole

ASJC Scopus subject areas

  • Organic Chemistry
  • Materials Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

Cite this

Synthesis and postpolymerization functionalization of poly(5-iodo-1,2,3- triazole)s. / Schwartz, Erik; Breitenkamp, Kurt; Fokin, Valery V.

In: Macromolecules, Vol. 44, No. 12, 28.06.2011, p. 4735-4741.

Research output: Contribution to journalArticle

Schwartz, Erik ; Breitenkamp, Kurt ; Fokin, Valery V. / Synthesis and postpolymerization functionalization of poly(5-iodo-1,2,3- triazole)s. In: Macromolecules. 2011 ; Vol. 44, No. 12. pp. 4735-4741.
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