Facile synthesis of well-defined hydrophilic methacrylic macromonomers using ATRP and click chemistry

Paul Topham, Nicolas Sandon, Elizabeth S. Read, Jeppe Madsen, Anthony J. Ryan, Steven P. Armes

Research output: Contribution to journalArticle

Abstract

A range of well-defined hydrophilic methacrylic macromonomers has been synthesized by the judicious combination of atom transfer radical polymerization (ATRP) and copper-catalyzed 1,3-dipolar cycloaddition (azide-alkyne click chemistry). An azido a-functionalized ATRP initiator was used to produce well-defined homopolymers with terminal azide functionality via ATRP in protic media at 20 °C, with generally good control being achieved over both target molecular weight and final polydispersity (Mw/Mn = 1.10-1.35). Suitable methacrylic monomers include 2-aminoethyl methacrylate hydrochloride, 2-(diethylamino)ethyl methacrylate, 2-(dimethylamino)ethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-(methacryloyloxy)ethyl phosphorylcholine, glycerol monomethacrylate, potassium 3-sulfopropyl methacrylate, and quaternized 2-(dimethylamino)ethyl methacrylate. These homopolymer precursors were then efficiently clicked using either propargyl methacrylate or propargyl acrylate to yield near-monodisperse (meth)acrylate-capped macromonomers with either cationic, anionic, nonionic, or zwitterionic character. Moreover, this generic route to well-defined hydrophilic macromonomers is also suitable for “one-pot” syntheses, as exemplified for 2-hydroxyethyl methacrylate and glycerol monomethacrylate-based macromonomers.
LanguageEnglish
Pages9542-9547
Number of pages6
JournalMacromolecules
Volume41
Issue number24
DOIs
Publication statusPublished - 14 Nov 2008

Fingerprint

Atom transfer radical polymerization
Azides
Homopolymerization
Glycerol
Phosphorylcholine
Alkynes
Cycloaddition
Methacrylates
Polydispersity
Potassium
Copper
Monomers
Molecular weight
acrylic acid
hydroxyethyl methacrylate
2-(dimethylamino)ethyl methacrylate

Keywords

  • atom transfer radical polymerization
  • ATRP
  • homopolymers
  • chemistry

Cite this

Topham, Paul ; Sandon, Nicolas ; Read, Elizabeth S. ; Madsen, Jeppe ; Ryan, Anthony J. ; Armes, Steven P. / Facile synthesis of well-defined hydrophilic methacrylic macromonomers using ATRP and click chemistry. In: Macromolecules. 2008 ; Vol. 41, No. 24. pp. 9542-9547.
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Facile synthesis of well-defined hydrophilic methacrylic macromonomers using ATRP and click chemistry. / Topham, Paul; Sandon, Nicolas; Read, Elizabeth S.; Madsen, Jeppe; Ryan, Anthony J.; Armes, Steven P.

In: Macromolecules, Vol. 41, No. 24, 14.11.2008, p. 9542-9547.

Research output: Contribution to journalArticle

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