Synthesis of lipo-glycopolymer amphiphiles by nitroxide-mediated living free-radical polymerization

被引:108
作者
Götz, H
Harth, E
Schiller, SM
Frank, CW
Knoll, W
Hawker, CJ
机构
[1] IBM Corp, Almaden Res Ctr, San Jose, CA 95120 USA
[2] Stanford Univ, Dept Chem Engn, Stanford, CA 94305 USA
[3] Max Planck Inst Polymer Res, D-55021 Mainz, Germany
关键词
living radical; nitroxide; lipopolymers; glycopolymers; block copolymers; biomacromolecules; amphiphiles; bioengineering;
D O I
10.1002/pola.10428
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The nitroxide-mediated living free-radical polymerization of 1,2,5,6-di(isopropylidene)-D-glucose-2-propenoate was achieved in dimethylformamide at 105 degreesC with an alpha-hydrido alkoxyamine initiator functionalized with a lipophilic N,N-di(octadecyl)amine group, The kinetics of the polymerization were investigated, and the mechanism was shown to be a living process allowing, after hydrolysis, controlled molecular weight, low-polydispersity lipo-glycopolymers to be prepared. The amphiphilic character of the macromolecule could be altered by either the exchange of the alkoxyamine at the chain end with hydrogen or the preparation of copolymers with lipophilic monomers such as N,N-di(octadecyl)acrylamide. The surface and membrane-forming properties of these novel lipopolymers demonstrate their amphiphilic character. (C) 2002 Wiley Periodicals, Inc.
引用
收藏
页码:3379 / 3391
页数:13
相关论文
共 70 条
  • [1] ADSORPTION OF CHAIN MOLECULES WITH A POLAR HEAD A-SCALING DESCRIPTION
    ALEXANDER, S
    [J]. JOURNAL DE PHYSIQUE, 1977, 38 (08): : 983 - 987
  • [2] Design and synthesis of water-soluble glycopolymers bearing breast tumor marker and enhanced lipophilicity for solid-phase assays
    Baek, MG
    Roy, R
    [J]. BIOMACROMOLECULES, 2000, 1 (04) : 768 - 770
  • [3] Diblock copolymers, micelles, and shell-crosslinked nanoparticles containing poly(4-fluorostyrene): Tools for detailed analyses of nanostructured materials
    Becker, ML
    Remsen, EE
    Wooley, KL
    [J]. JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2001, 39 (23) : 4152 - 4166
  • [4] Development of a universal alkoxyamine for "living" free radical polymerizations
    Benoit, D
    Chaplinski, V
    Braslau, R
    Hawker, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (16) : 3904 - 3920
  • [5] One-step formation of functionalized block copolymers
    Benoit, D
    Hawker, CJ
    Huang, EE
    Lin, ZQ
    Russell, TP
    [J]. MACROMOLECULES, 2000, 33 (05) : 1505 - 1507
  • [6] Kinetics and mechanism of controlled free-radical polymerization of styrene and n-butyl acrylate in the presence of an acyclic β-phosphonylated nitroxide
    Benoit, D
    Grimaldi, S
    Robin, S
    Finet, JP
    Tordo, P
    Gnanou, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (25) : 5929 - 5939
  • [7] Bon SAF, 2000, J POLYM SCI POL CHEM, V38, P2678, DOI 10.1002/1099-0518(20000801)38:15<2678::AID-POLA70>3.0.CO
  • [8] 2-P
  • [9] Chen YM, 2002, MACROMOL RAPID COMM, V23, P59, DOI 10.1002/1521-3927(20020101)23:1<59::AID-MARC59>3.0.CO
  • [10] 2-V