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

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• 作者：Hunaid Nulwala ; Kenichi Takizawa ; Anika Odukale ; Anzar Khan ; Raymond J. Thibault ; Benjamin R. Taft ; Bruce H. Lipshutz ; Craig J. Hawker
• 刊名：Macromolecules
• 出版年：2009
• 出版时间：August 25, 2009
• 年：2009
• 卷：42
• 期：16
• 页码：6068-6074
• 全文大小：895K
• 年卷期：v.42,no.16(August 25, 2009)
• ISSN：1520-5835

文摘

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 ¹H NMR, ¹³C 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.