Selective and orthogonal post-polymerization modification using sulfur(VI) fluoride exchange (SuFEx) and copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions

James S. Oakdale, Luke Kwisnek, Valery V. Fokin

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

Functional polystyrenes and polyacrylamides, containing combinations of fluorosulfate, aromatic silyl ether, and azide side chains, were used as scaffolds to demonstrate the postpolymerization modification capabilities of sulfur(VI) fluoride exchange (SuFEx) and CuAAC chemistries. Fluorescent dyes bearing appropriate functional groups were sequentially attached to the backbone of the copolymers, quantitatively and selectively addressing their reactive partners. This combined SuFEx and CuAAC approach proved to be robust and versatile, allowing for a rare accomplishment: triple orthogonal functionalization of a copolymer under essentially ambient conditions without protecting groups.

Original languageEnglish
Pages (from-to)4473-4479
Number of pages7
JournalMacromolecules
Volume49
Issue number12
DOIs
Publication statusPublished - 28 Jun 2016
Externally publishedYes

Fingerprint

Alkynes
Azides
Cycloaddition
Fluorides
Sulfur
Copper
Ion exchange
Bearings (structural)
Copolymers
Polymerization
Polystyrenes
Polyacrylates
Fluorescent Dyes
Scaffolds
Ether
Functional groups
Ethers
Dyes
polyacrylamide

ASJC Scopus subject areas

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

Cite this

Selective and orthogonal post-polymerization modification using sulfur(VI) fluoride exchange (SuFEx) and copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. / Oakdale, James S.; Kwisnek, Luke; Fokin, Valery V.

In: Macromolecules, Vol. 49, No. 12, 28.06.2016, p. 4473-4479.

Research output: Contribution to journalArticle

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