A Modular Route for the
Synthesis of ABC Miktoarm
Star Terpolymers via a New Alkyne-Substituted Diphenylethylene Derivative
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Abstract
We introduce a modular route for the synthesis of well-defined
ABC miktoarm star terpolymers. To this aim, the synthesis of a 1,1-diphenylethylene
derivative bearing a protected alkyne function (1-[(4-(<i>tert</i>-butyldimethylsilyl)ethynyl)phenyl]-1-phenylethylene) was developed.
This compound was for the first time employed in sequential anionic
polymerization to readily prepare alkyne mid-functionalized diblock
copolymers with polybutadiene as first and a poly(alkyl methacrylate)
(poly(<i>tert</i>-butyl methacrylate), poly(<i><i>N,N</i></i>-dimethylaminoethyl methacrylate)) as second
block. For the third arm controlled radical polymerization methods
(polystyrene, poly(<i>tert</i>-butyl methacrylate), poly(<i><i>N,N</i></i>-dimethylaminoethyl methacrylate)) and
anionic ring-opening polymerization (poly(ethylene oxide)) were used
to separately prepare homopolymers with an azido function. Afterward,
azide–alkyne Huisgen cycloaddition was successfully employed
to synthesize a library of ABC miktoarm star terpolymers with different
molecular weights and chemical compositions via modular combination
of the functionalized diblock copolymers and homopolymers. The resulting
new ABC miktoarm star terpolymers showed narrow, monomodal molecular
weight distributions with dispersities typically below 1.10, as determined
by size exclusion chromatography