Synthesis and Characterization of Isomeric Vinyl-1,2,3-triazole Materials by Azide-Alkyne Click Chemistry

被引：75
|
作者：
Nulwala, Hunaid [1 ,2 ,3 ]
Takizawa, Kenichi [1 ,2 ,4 ]
Odukale, Anika [1 ,2 ]
Khan, Anzar [1 ,2 ]
Thibault, Raymond J. [1 ,2 ,5 ]
Taft, Benjamin R. [3 ]
Lipshutz, Bruce H. [3 ]
Hawker, Craig J. [1 ,2 ,3 ]
机构：
[1] Univ Calif Santa Barbara, Mat Res Lab, Santa Barbara, CA 93106 USA
[2] Univ Calif Santa Barbara, Dept Mat, Santa Barbara, CA 93106 USA
[3] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
[4] Mitsubishi Chem Grp Sci & Technol Res Ctr Inc, Aoba Ku, Yokohama, Kanagawa 2278502, Japan
[5] Dow Chem Co USA, Freeport, TX 77598 USA
来源：
MACROMOLECULES | 2009年 / 42卷 / 16期
基金：
美国国家科学基金会;
关键词：
RUTHENIUM-CATALYZED CYCLOADDITION; 1,3-DIPOLAR CYCLOADDITIONS; BIFUNCTIONAL DENDRIMERS; RADICAL POLYMERIZATION; RAFT POLYMERIZATION; ADHESIVE POLYMERS; VERSATILE; FUNCTIONALIZATION; NANOPARTICLES; COPOLYMERS;
D O I：
10.1021/ma900892h
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 synthesis of isomeric, functionalized 4-vinyl-1,2,3-triazole and 5-vinyl-1,2,3-triazole monomers is demonstrated using heterogeneous copper (copper-in-charcoal)-catalyzed azide-alkyne cycloaddition (CuAAC) or homogeneous ruthenium (Ru)-catalyzed azide-alkyne cycloadditions (RuAAC) "click" protocols. These reactions are regiospecific, exclusively forming 1,4- and 1, 5-disubstituted triazoles as determined by H-1 NMR, C-13 NMR, and X-ray crystallography analysis. Polymerizations were performed using living free radical procedures to yield materials with divergent properties. In the case of the 1,5-triazole materials, glass transition temperature were significantly higher that for the 1,4-derivatives while solubility was decreased.
引用
收藏
页码：6068 / 6074
页数：7
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