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

Macromol Rapid Commun. 2011 Sep 1;32(17):1362-6. doi: 10.1002/marc.201100324.

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 amine-functional polymers and block copolymers. Poly(spiro[6-methyl-1,4-dioxane-2,5-dione-3,2'-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.

Keywords: diels-Alder reactions; poly(ester); poly(lactide); post-polymerization modification; tetrazine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Catalysis
  • Click Chemistry
  • Dioxanes / chemistry*
  • Norbornanes / chemistry*
  • Polyesters / chemical synthesis*
  • Polymerization
  • Pyridines / chemistry*

Substances

  • 3,6-bis(2-pyridyl)-1,2,4,5-tetrazine
  • Bridged Bicyclo Compounds
  • Dioxanes
  • Norbornanes
  • Polyesters
  • Pyridines
  • poly(lactide)
  • dilactide