Click chemistry with poly(2-oxazoline)s

被引:154
作者
Luxenhofer, Robert
Jordan, Rainer
机构
[1] Tech Univ Munich, Dept Chem, Lehrstuhl Makromol Stoffe, D-85747 Garching, Germany
[2] Polytech Univ, Dept Chem Chem Engn & Mat Sci, Brooklyn, NY 11201 USA
关键词
D O I
10.1021/ma052515m
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
A new 2-oxazoline with a pendant alkyne moiety, 2-(pent-4-ynyl)-2-oxazoline, 1 (PynOx), was synthesized from commercial available compounds. Polymerization of PynOx with methyl triflate as initiator and copolymerization with 2-methyl- or 2-ethyl-2-oxazoline (MeOx or EtOx) as comonomers results in well-defined water-soluble polymers of narrow molar mass distributions and predefined degrees of polymerization. Since the alkyne moiety is compatible with the living cationic polymerization, no protection group was needed. The consecutive copper-catalyzed Huisgen 1,3-dipolar cycloadditions of two different azides with the polymer bound alkynes to the 1,2,3-triazoles were quantitative.
引用
收藏
页码:3509 / 3516
页数:8
相关论文
共 33 条
[1]   ENTRY INTO 6-METHOXY-D(+)-TRYPTOPHANS - STEREOSPECIFIC SYNTHESIS OF 1-BENZENESULFONYL-6-METHOXY-D(+)-TRYPTOPHAN ETHYL-ESTER [J].
ALLEN, MS ;
HAMAKER, LK ;
LALOGGIA, AJ ;
COOK, JM .
SYNTHETIC COMMUNICATIONS, 1992, 22 (14) :2077-2102
[3]   Combining ring-opening metathesis polymerization (ROMP) with sharpless-type "click" reactions: An easy method for the preparation of side chain functionalized poly(oxynorbornenes) [J].
Binder, WH ;
Kluger, C .
MACROMOLECULES, 2004, 37 (25) :9321-9330
[4]  
Binder WH, 2000, MACROMOL CHEM PHYSIC, V201, P949, DOI 10.1002/1521-3935(20000601)201:9<949::AID-MACP949>3.0.CO
[5]  
2-0
[6]   Template assembled cyclopeptides as multimeric system for integrin targeting and endocytosis [J].
Boturyn, D ;
Coll, JL ;
Garanger, E ;
Favrot, MC ;
Dumy, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5730-5739
[7]   First poly(2-oxazoline)s with pendant amino groups [J].
Cesana, S ;
Auernheimer, J ;
Jordan, R ;
Kessler, H ;
Nuyken, O .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2006, 207 (02) :183-192
[8]   Click chemistry in materials synthesis.: 1.: Adhesive polymers from copper-catalyzed azide-alkyne cycloaddition [J].
Díaz, DD ;
Punna, S ;
Holzer, P ;
Mcpherson, AK ;
Sharpless, KB ;
Fokin, VV ;
Finn, MG .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (17) :4392-4403
[9]   The dawning era of polymer therapeutics [J].
Duncan, R .
NATURE REVIEWS DRUG DISCOVERY, 2003, 2 (05) :347-360
[10]  
DUNCAN R, 2004, 6 INT S POL THER CAR