6533b7d3fe1ef96bd1261429

RESEARCH PRODUCT

PEG-based Multifunctional Polyethers with Highly Reactive Vinyl-Ether Side Chains for Click-Type Functionalization

Frederik R. WurmCarsten DingelsHolger FreyBoris ObermeierChristine Mangold

subject

Polymers and PlasticsCyanideEpoxideRing-opening polymerizationPolymerizationInorganic Chemistrychemistry.chemical_compoundThiolsPolymer chemistryMaterials ChemistrymedicineOrganic chemistryPoly(Ethylene Glycol) CopolymersOxide)Ethylene oxideMonomersOrganic Chemistrytechnology industry and agricultureVinyl etherAnionic addition polymerizationchemistryPolymerizationGlycidolBlock-CopolymersFree-Radical AdditionAlkoxy groupEthylene glycolDerivativesmedicine.drug

description

Introduction of highly reactive vinyl ether moieties along a poly(ethylene-glycol) (PEG) backbone has been realized by copolymerization of the novel epoxide monomer ethoxy vinyl glycidyl ether (EVGE) with ethylene oxide (EO). A series of copolymers with varying structure (block and random) as well as EVGE comonomer content (5-100%) with molecular weights in the range of 3,900-13,200 g/mol and narrow molecular weight distributions (M-w/M-n = 1.06-1.20) has been synthesized and characterized with respect to their microstructure and thermal properties. The facile transformation of the vinyl ether side chains in click type reactions was verified by two different post polymerization modification reactions: (i) thiol-ene addition and (ii) acetal formation, employing various model compounds. Both strategies are very efficient, resulting in quantitative conversion. The rapid and complete acetal formation with alcohols results in an acid-labile bond and is thus highly interesting with respect to biomedical applications that require slow or controlled release of a drug, while the thiol-ene addition to a vinyl ether prevents cross-linking efficiently compared to other double bonds.

yearjournalcountryeditionlanguage
2011-07-22Macromolecules
https://doi.org/10.1021/ma200898n