Issue 12, 2011

Synthesis of ABC type miktoarm star copolymers by triple click chemistry

Abstract

An ABC type miktoarm star copolymer possessing polystyrene (PS), poly(ε-caprolactone) (PCL) and poly(ethylene glycol) (PEG) arms was synthesized by combining existing triple click chemistries, namely thiol–ene, copper catalyzed azide–alkyne cycloaddition (CuAAC) and Diels–Alder (DA) reactions. For this purpose, a core (1-(allyloxy)-3-azidopropan-2-yl (anthracen-9-ylmethyl) succinate) with allyl, azide and anthracene functionalities was synthesized in two steps with high yields. Then, polymers with corresponding clickable sites, namely ω-thiol polystyrene (PS-SH), α-alkyne poly(ε-caprolactone) (alkyne-PCL) and ω-maleimide poly(ethylene glycol) (Me-PEG-MI), were independently prepared. As the first step of the grafting onto process, PS-SH was thiol–ene clicked onto the core to yield PS-N3-Ant. Finally, alkyne-PCL and Me-PEG-MI were bonded to PS-N3-Ant either in a sequential or a one-pot in situ manner using CuAAC and DA click reactions. All intermediates, related polymers at different stages and final PS-PCL-PEG miktoarm star copolymer were characterized by 1H NMR, FT-IR, and GPC analyses.

Graphical abstract: Synthesis of ABC type miktoarm star copolymers by triple click chemistry

Supplementary files

Article information

Article type
Paper
Submitted
08 Aug 2011
Accepted
21 Sep 2011
First published
17 Oct 2011

Polym. Chem., 2011,2, 2865-2871

Synthesis of ABC type miktoarm star copolymers by triple click chemistry

B. Iskin, G. Yilmaz and Y. Yagci, Polym. Chem., 2011, 2, 2865 DOI: 10.1039/C1PY00352F

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