Simultaneous dual end-functionalization of peg via the passerini three-component reaction for the synthesis of ABC miktoarm terpolymers

Authors

  • Lei Li,

    1. Department of Polymer Science and Engineering, Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China
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  • Xiao-Wei Kan,

    1. Department of Polymer Science and Engineering, Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China
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  • Xin-Xing Deng,

    1. Department of Polymer Science and Engineering, Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China
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  • Cheng-Cheng Song,

    1. Department of Polymer Science and Engineering, Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China
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  • Fu-Sheng Du,

    1. Department of Polymer Science and Engineering, Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China
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  • Zi-Chen Li

    Corresponding author
    1. Department of Polymer Science and Engineering, Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China
    • Department of Polymer Science and Engineering, Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Polymer Chemistry and Physics of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, People's Republic of China
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Abstract

In this article, we demonstrate the Passerini three-component reaction as a simple, effective method for the synthesis of polymers with double functional end groups, which are key precursors for the preparation of ABC miktoarm terpolymers. Thus, via the one-step Passerini reaction of monomethoxy poly(ethylene glycol)–propionaldehyde (PEG-CHO) with 2-bromo-2-methylpropionic acid and propargyl isocyanoacetamide, the PEG chain end was simultaneously functionalized with one atom transfer radical polymerization (ATRP) initiating site and one alkynyl group. The resulting PEG(-alkynyl)-Br was then used for the synthesis of three types of miktoarm ABC terpolymers via two approaches. First, we conducted ATRP of N-isopropylacrylamide (NIPAM), then click reaction with azido-terminated polystyrene (PS-N3) or poly(tert-butyl acrylate) (PtBA-N3) and obtained two ABC miktoarm terpolymers PEG(-b-PNIPAM)-b-PS and PEG(-b-PNIPAM)-b-PtBA. Alternatively, we conducted single electron transfer living radical polymerization of tBA and click reaction with PS-N3 simultaneously to give PEG(-b-PtBA)-b-PS. All the polymer precursors and miktoarm terpolymers have been characterized by 1H NMR, Fourier transform infrared, gel permeation chromatography, demonstrating that both approaches provided well-defined ABC miktoarm terpolymers. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

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