2-Iso-propyl-2-oxazoline: a Versatile Monomer for Functionalization of Polymers obtained via RAFT
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Weber, Christine; Neuwirth, Toni; Kempe, Kristian; Ozkahraman, Bengi; Tamahkar, Emel; Mert, Humeyra; Becer, C. Remzi; Schubert, Ulrich S.
- Abstract:
- 2-Isopropenyl-2-oxazoline (iPOx) was polymerized
for the first time via a controlled radical polymerization
technique. Reversible addition−fragmentation chain transfer
(RAFT) polymerization utilizing a dithiobenzoate-based chain
transfer agent was employed to form a backbone that is highly
reactive toward thiols and acids. Moreover, the statistical
copolymerization of iPOx with methyl methacrylate (MMA)
and N-iso-propylacrylamide (NiPAm) was investigated resulting
in two copolymer series with iPOx content varying from
100% to 13% (PDI = 1.37 to 1.21). The P(iPOx-stat-NiPAm)
copolymers displayed thermoresponsive behavior in water as well as phosphate buffered saline at higher temperatures in
comparison to homopolymers of NiPAm due to the hydrophilicity of the introduced iPOx moieties (Tcp = 25 to 75 °C).
Futhermore, iPOx-based (co)polymers were functionalized by polymer analogous addition reactions with thiophenol, benzoic
acid and 4-azidobenzoic acid in high conversions (74−100%). The latter adduct represented a suitable building block for the
synthesis of a graft copolymer consisting of a PMMA backbone and poly(2-ethyl-2-oxazoline) (PEtOx) side chains via coppercatalyzed
azide−alkyne cycloaddition (CuAAC) of PEtOx with alkyne terminus.
- Year:
- 2012
- Type of Publication:
- Article
- Journal:
- Macromolecules
- Volume:
- 45
- Pages:
- 20-27