Preparation and characterization of 1,2,3‐triazole‐cured polymers from endcapped azides and alkynes

Abstract

Fourteen commercial polyols have been characterized by GPC, NMR spectroscopy, and elemental analysis. From these, eight corresponding tosylates, six nitrate esters, seven mesylates, 13 alkynes, and 14 azides have been prepared and all these derivatives have been fully characterized. Five alkyne monomers and eight azide monomers were also prepared. Twelve alkynes and 13 azides (functionality 2–4) were combined in 1,3‐dipolar cycloaddition reactions under neat conditions to prepare triazole‐cured polymers, avoiding any heavy metal catalyst. Characterization by NMR spectroscopy, elemental analysis, and gel permeation chromatography indicated triazole polymers 14, 22, 23, 28, and 30 with degrees of polymerization of 17–28 to be the best candidates for future work. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 238–256, 2008

Construction of Linear Polymers, Dendrimers, Networks, and Other Polymeric Architectures by Copper‐Catalyzed Azide‐Alkyne Cycloaddition “Click” Chemistry

“…Recently, Katritzky et al reported a similar study wherein a library of multifunctional azides and alkynes were polymerized in solution and characterized by standard techniques. [121] Finn and coworkers also utilized two of their previously studied adhesive molecules, tripropargyl amine with 1,6-diazidohexane, in a solution phase CuAAC reaction to yield a highly crosslinked polymer which was observed to reversibly swell and deswell when treated with trifluoroacetic acid due to the amine functionalities within the material (Scheme 22). [122] The authors suggest that the polarity, stability, and p-stacking properties of the triazole products can potentially be exploited for a range of applications, a notion that has been abundantly confirmed by reports that have appeared in the past few years.…”

Synthesis of Novel Labdanoid-Based Macroheterocycles Using Click-Cycloaddition Reaction Protocol

“…[22] 1,10-Diazidodecane 8, [23] 1-azido-2-(2-azidoethoxy) ethane 9 [24] are known compounds and were prepared by the reported methods. Chemicals used -LiAlH 4 , POCl 3 , NaBH 4 , NaH, 80 % solution of propargyl bromide in PhMe, sodium ascorbate, CuSO (4).…”

Synthesis of new polyimides with 1,2,3-triazole units

“…The azide group is known to react with propargyl groups by [3+2] cycloaddition reaction, in the presence of catalyst Cu (I) or not, to give 1,2,3-triazole rings [8][9][10][11][12]. The pathway of cycloaddition reaction is presented in Scheme 3.…”