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Efficient Synthesis of High Purity Homo‐arm and Mikto‐arm Poly(ethylene glycol) Stars Using Epoxide and Azide–Alkyne Coupling Chemistry
Author(s) -
Zhang Boyu,
Zhang Hong,
Elupula Ravinder,
Alb Alina M.,
Grayson Scott M.
Publication year - 2014
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.201300623
Subject(s) - alkyne , azide , ethylene glycol , epoxide , polymer chemistry , polyethylene glycol , click chemistry , chemistry , end group , polymerization , polymer , materials science , organic chemistry , catalysis
High purity homo‐arm and mikto‐arm poly(ethylene glycol) (PEG) stars are successfully prepared by the combination of epoxide ring‐openings and azide–alkyne click reactions. First, monohydroxy‐PEG was modified via epoxide chemistry to bear one hydroxyl and one azide functionality at the same end. An alkyne‐functionalized PEG chain was then coupled to the azide. Subsequently, the remaining hydroxyl could be reactivated to an azide again and again to enable stepwise addition of alkyne‐functionalized polymer arms. The use of efficient reactions for this iterative route provides star polymers with an exact number of arms, and a tailorable degree of polymerization for each arm. Detailed characterization confirms the high purity of multi‐arm polyethylene glycol products.