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Synthesis of Amphiphilic Tadpole-shaped PS-b-(c-PEO) Copolymers by the Combination of Glaser Coupling with Living Anionic Polymerization and Ring-opening Polymerization
WANG Guowei 1 #,HU Bin 2,FAN Xiaoshan 2,ZHANG Yannan 2,HUANG Junlian* 2 *
1.The Key Laboratory of Molecular Engineering of Polymer, State Education Ministry of China, Department of Macromolecular Science, Fudan University
2.The Key Laboratory of Molecular Engineering of Polymer, State Education Ministry of China, Department of Macromolecular Science, Fudan University, Shanghai 200433, China
*Correspondence author
#Submitted by
Subject:
Funding: The Specialized Research Fund for the Doctoral Program of Higher Education of China （No.No. 20090071120015）, The Natural Science Foundation of China （No.No. 21004011）
Opened online:30 May 2011
Accepted by: none
Citation: WANG Guowei,HU Bin,FAN Xiaoshan.Synthesis of Amphiphilic Tadpole-shaped PS-b-(c-PEO) Copolymers by the Combination of Glaser Coupling with Living Anionic Polymerization and Ring-opening Polymerization[OL]. [30 May 2011] http://en.paper.edu.cn/en_releasepaper/content/4428451
 
 
The tadpole-shaped copolymers polystyrene(PS)-b-[cyclic poly(ethylene oxide)(PEO)] [PS-b-(c-PEO)] contained linear tail chains of PS and cyclic head chains of PEO were synthesized by combination of glaser coupling with living anionic polymerization (LAP) and ring-opening polymerization (ROP). Firstly, the functionalized polystyrene-glycerol (PS-Gly) with two active hydroxyl groups at ω end was synthesized by LAP of St and the subsequent capping with 1-ethoxyethyl glycidyl ether (EEGE) and then deprotection of protected hydroxyl group in acid condition. Then, using PS-Gly as macro-initiator, the ROP of EO was carried out using diphenylmethylpotassium(DPMK) as co-catalyst for AB2 star-shaped copolymers PS-b-(PEO-OH)2, and the alkyne group was introduced onto PEO arm end for PS-b-(PEO-Alkyne)2. Finally, The intramolecular cyclization was carried out by glaser coupling reaction in pyridine /Cu(I)Br /N,N,N',N'',N''-pentamethyldiethylenetri-amine (PMDETA) system under room temperature, and tadpole-shaped PS-b-(c-PEO) with high efficiency (almost 100%) was formed. The target copolymers and their intermediates were well characterized by SEC, 1H NMR and FT-IR in details. The critical micelle concentration (CMC) and the thermal properties were also determined and compared to investigate the influence of architecture on properties. The results showed that tadpole-shaped copolymers had higher CMC values and lower Tm, Tc, Xc than that of their precursors of star-shaped copolymers.
Keywords:Polymer chemistry; Glaser Coupling; Star-shaped; Tadpole-shaped; Poly(ethylene oxide)(PEO); Polystyrene (PS)
 
 
 

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