Efficient Polymer-Polymer Conjugation via Thiol-ene Click Reaction
| Autor: | Benjamin D. Fairbanks, Dillon M. Love, Christopher N. Bowman |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Polymers and Plastics Alkene Organic Chemistry 02 engineering and technology 010402 general chemistry 021001 nanoscience & nanotechnology Condensed Matter Physics 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Photopolymer chemistry Reagent PEG ratio Polymer chemistry Materials Chemistry Click chemistry Ammonium persulfate Physical and Theoretical Chemistry 0210 nano-technology Ene reaction Norbornene |
| Zdroj: | Macromolecular Chemistry and Physics. 218:1700073 |
| ISSN: | 1022-1352 |
| Popis: | Despite the rapid reaction rates and high efficiency of the radical-mediated thiol-ene reactions in high concentrations, complications arise when implementing this reaction under dilute conditions, such as those often requisite for polymer-polymer conjugation. Here, we briefly review some of the challenges inherent in polymer modification via thiol-ene reactions and demonstrate several successful polymer couplings (including star polymer assembly) under a variety of conditions with coupling efficiencies exceeding 91% achieved with appropriate initiator and terminal functional group selection. Generally, the results indicate thermal initiation with an “azobis” initiator was unsuccessful in polymer-polymer conjugation of a thiol-terminated poly(ethylene glycol) (PEG) to an alkene terminated PEG. Reduction-oxidation initiators, both ammonium persulfate and Fe(II) and Fenton's reagent were effective in conjugating thiol terminated PEG to norbornene terminated PEG, but not to an allyl ether terminated PEG. Type I photoinitiators, in particular a water soluble acyl phosphinate, were more effective than either the examined thermal or redox initiators for thiol-ene polymer-polymer conjugations generally. |
| Databáze: | OpenAIRE |
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