title: Tetrazine-norbornene click reactions to functionalize degradable polymers derived from lactide.
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.
authors: Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK.
authors: Ian A
authors: IA
authors: Barker
authors: Daniel J
authors: DJ
authors: Hall
authors: Claire F
authors: CF
authors: Hansell
authors: Filip E
authors: FE
authors: Du Prez
authors: Rachel K
authors: RK
authors: O'Reilly
authors: Andrew P
authors: AP
authors: Dove
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D057930:Click Chemistry; D004146:Dioxanes / Q000737:chemistry*; D009636:Norbornanes / Q000737:chemistry*; D011091:Polyesters / Q000138:chemical synthesis*; D058105:Polymerization; D011725:Pyridines / Q000737:chemistry*
chemical_list: C505506:3,6-bis(2-pyridyl)-1,2,4,5-tetrazine; D001643:Bridged Bicyclo Compounds; D004146:Dioxanes; D009636:Norbornanes; D011091:Polyesters; D011725:Pyridines; C033616:poly(lactide); C091880:dilactide
keywords: diels-Alder reactions; poly(ester); poly(lactide); post-polymerization modification; tetrazine