Tetrazine-norbornene click reactions to functionalize degradable polymers derived from lactidea

Ian A. Barker, Daniel J. Hall, Claire F. Hansell, Filip E. Du Prez, Rachel K. O'Reilly, Andrew P. Dove

Research output: Contribution to journalArticleResearchpeer-review

45 Citations (Scopus)

Abstract

Post-polymerization modification of polymers derived from sustainable resources using the click reaction between tetrazines and norbornenes is shown to provide a mild and efficient route for the synthesis of functional degradable polymers. Norbornene chain-end functional poly(lactide) was synthesized using organocatalytic methods and functionalized by the addition of 3,6-di-2-pyridyl-1,2,4,5-tetrazine without degradation of the polymer backbone. The versatility of this reaction was demonstrated by the application of analogues bearing amine and poly(ethylene oxide) groups to realize aminefunctional polymers and block copolymers. Poly- (spiro[6-methyl-1,4- dioxane-2,5-dione-3,20-bicyclo- [2.2.1]hept[5]ene]) was prepared from lactide. The pendant norbornene group on the backbone of the resultant polymer was modified in a similar manner to produce functional degradable polymers and graft co-polymers.

Original languageEnglish
Pages (from-to)1362-1366
Number of pages5
JournalMacromolecular Rapid Communications
Volume32
Issue number17
DOIs
Publication statusPublished - 1 Sep 2011
Externally publishedYes

Keywords

  • Diels-Alder reactions
  • Poly(ester)
  • Poly(lactide)
  • Postpolymerization modification
  • Tetrazine

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