A first generation phosphorus-containing dendrimer with twelve terminal benzyl dithiobenzoate functions was designed and subsequently used as a multifunctional agent to derive hybrid star copolymers consisting of a dendritic core surrounded by twelve polystyrene branches by reversible addition-fragmentation chain transfer (RAFT).
A new functional lactone, α-iodo-ε-caprolactone (αIεCL), was synthesized from ε-caprolactone by anionic activation using a non-nucleophilic strong base (lithium diisopropylamide) followed by an electrophilic substitution with iodine chloride. Ring-opening (co)polymerizations of the resulting monomer with ε-caprolactone were carried out using tin 2-ethylhexanoate as a catalyst in toluene at 100 °C. Homopolymerization of αIεCL was achieved, and poly(αIεCL) was fully characterized by SEC, (1) H NMR and elemental analysis. Random copolymerizations of αIεCL with εCL were controlled with experimental molecular weights close to the theoretical values, narrow molecular weight distributions and a good agreement between experimental and theoretical molar compositions of αIεCL.
A straightforward approach based on thiol-ene click chemistry was used to prepare novel functional polyesters containing amino groups. First, a series of well-defined alkene-functional poly(3caprolactone)s were prepared by ring-opening polymerization of a-allyl-3-caprolactone with 3caprolactone in toluene and in bulk using tin 2-ethylhexanoate as catalyst. These functional polyesters were fully characterized by 1 H NMR, GPC, and MALDI-TOF MS. The resulting random copolyesters were obtained with a wide range of molar masses from 3000 to 50 000 g mol À1 and a good incorporation of the a-allyl-3-caprolactone monomer unit. Then, thiol-ene reaction of alkene-functional PCL with the 2-(Boc-amino)ethanethiol was used to prepare efficiently polyesters bearing protected amino groups without chain degradation. Finally, cationic and water-soluble polyesters bearing free amino groups were recovered by cleavage of the Boc protecting group. These aminated polyesters were characterized by 1 H NMR in deuterated water.
Well-defined graft copolymers were obtained using a copper-catalysed azide-alkyne Huisgen's cycloaddition click reaction from both biocompatible and non-toxic poly(ε-caprolactone) and poly(2-methyl-2-oxazoline) homopolymers. Resulting amphiphilic copolymers proved to form micelles that could be used as potential drug carriers.
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