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Tetrazine‐Norbornene Click Reactions to Functionalize Degradable Polymers Derived from Lactide
Author(s) -
Barker Ian A.,
Hall Daniel J.,
Hansell Claire F.,
Du Prez Filip E.,
O'Reilly Rachel K.,
Dove Andrew P.
Publication year - 2011
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201100324
Subject(s) - norbornene , polymer , copolymer , polymer chemistry , ethylene oxide , polymerization , click chemistry , lactide , materials science , functional polymers , amine gas treating , polyester , tetrazine , chemistry , organic chemistry
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.