Highly efficient synthesis of polymer brushes with PEO and PCL as side chains via click chemistry

Peng Zhao, Yechao Yan, Xiaoqin Feng, Lixin Liu, Chun Wang, Yongming Chen

Research output: Contribution to journalArticlepeer-review

53 Scopus citations

Abstract

We reported that well-defined polymer brushes could be prepared efficiently via the grafting-onto approach and the polymer brushes grafted with poly(ethylene oxide) (PEO), poly(ε-caprolactone) (PCL) and mixed PEO/PCL have been obtained. Firstly, poly(glycidyl methacrylate)s, PG100 and PG940, were prepared by controlled radical polymerization and their epoxy groups were reacted with sodium azide to introduce azido groups quantitatively. Then the PG derivatives bearing azido groups, poly(3-azido-2-hydroxypropyl methacrylate)100 (PGA100), were reacted with the alkynyl terminated either PEO (ay-PEO113) or PCL (ay-PCL17) through copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction under mild temperature. At a molar feed ratio of ay-PEO 113:azido unit = 1:1, the coupling reaction with ay-PEO113 proceeded nearly quantitatively. At the same feed, the conversion of grafting ay-PCL17 dropped to ca. 80%. Amphiphilic polymer brushes with randomly grafted PEO and PCL branches were also obtained by feeding the mixed ay-PEO and ay-PCL during CuAAC. By coupling ay-PEO113 onto a long backbone PGA940, wormlike PEO brushes with an average length of 140 nm were prepared as demonstrated by AFM. This molecular worm was further labeled with Rhodamine B and then was incubated with liver cancer cells HepG2. Preliminary results indicated that the wormlike brushes could be internalized by the cells easily, suggesting the potential application as advanced vehicles for delivery.

Original languageEnglish (US)
Pages (from-to)1992-2000
Number of pages9
JournalPolymer
Volume53
Issue number10
DOIs
StatePublished - Apr 25 2012

Bibliographical note

Funding Information:
Financial support from NSFC ( 21090350 , 21090353 , and 21128003 ), the Knowledge Innovation Program of the Chinese Academy of Sciences (Grant No. KJCX2-YW-H19 ), K. C. Wong Education Foundation (Hong Kong), and SKLSSM ( 201015 ) is gratefully acknowledged.

Keywords

  • Click chemistry
  • Grafted polymers
  • Poly(ε-caprolactone)

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