Web Release Date: January 26,
Combination of Ring-Opening Polymerization and "Click" Chemistry
for the Synthesis of an Amphiphilic Tadpole-Shaped
Poly(
-Caprolactone) Grafted by PEO
Center for Education and Research on Macromolecules (CERM), University of Liège, Sart-Tilman, B6, 4000 Liège, Belgium
Received October 27, 2006
Revised Manuscript Received December 14, 2006
Abstract:
A tadpole shaped poly(-caprolactone) (PCL; Mn = 24 500) was made amphiphilic by grafting
the two PCL tails with PEO. In the first step, a macrocyclic PCL was synthesized by ring-opening polymerization
of -caprolactone (CL) initiated by a cyclic tin(IV) dialkoxide and stabilized by local intramolecular photo-cross-linking. In the second step, the polymerization of a mixture of CL and 
-chloro--caprolactone (ClCL)
was resumed with formation of two activated chloride containing PCL tails. In the third step, the chlorides were
converted into azides onto which alkynyl end-capped PEO was grafted by the copper-mediated Huisgen's
cycloaddition [3 + 2], thus giving a "click" reaction. The thermal properties of the final copolymer and the
precursors were analyzed by differential scanning calorimetry. The amphiphilicity of the final copolymer was
confirmed by micellization in water.
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