Kinetic studies of CuBr-PMDETA catalyzed 1,3-dipolar cycloaddition polymerization

被引:1
作者
Liu, Rongpeng [1 ]
Zhang, Bing [1 ]
Wan, Liqiang [1 ]
Huang, Farong [1 ]
Du, Lei [1 ]
机构
[1] E China Univ Sci & Technol, Key Lab Specially Funct Polymer Mat & Related Tec, Minist Educ, Shanghai 200237, Peoples R China
来源
JOURNAL OF MACROMOLECULAR SCIENCE PART A-PURE AND APPLIED CHEMISTRY | 2016年 / 53卷 / 06期
关键词
Click reaction; kinetics; apparent activation energy; step-growth polymerization; CLICK CHEMISTRY; ADHESIVE POLYMERS; DIAZIDE; LIGANDS; AZIDES;
D O I
10.1080/10601325.2016.1166003
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 kinetics for the reaction of diazide (4,4'-biphenyl dibenzyl azide) and diyne (dipropargyl bisphenol A) catalyzed by CuBr-PMDETA (N, N, N', N '', N ''-pentamethyldiethylenetriamine) was studied in this paper by means of nuclear magnetic resonance spectra (H-1-NMR) and differential scanning calorimetry (DSC). H-1-NMR was carried out to analyze solution polymerizations under different CuBr-PMDETA ratios in DMSO-d(6). The results showed that CuBr-PMDETA catalytic system was easy to be oxidation under ambient condition. However, different CuBr-PMDETA ratios influenced the catalytic efficiency and the optimal ratios were found in nitrogen gas. DSC was carried out to analyze bulk polymerizations. The results showed that the apparent activation energy (E-alpha) calculated by Kissinger's method was 69.2 kJ/mol, which was confirmed by Friedman's method. The two tests indicated that the catalyzed polymerization of diazide and diyne was a second order reaction.
引用
收藏
页码:368 / 373
页数:6
相关论文
共 35 条
[1]   'Click' chemistry in polymer and material science: An update [J].
Binder, Wolfgang H. ;
Sachsenhofer, Robert .
MACROMOLECULAR RAPID COMMUNICATIONS, 2008, 29 (12-13) :952-981
[2]   Characterization of an amylose-graft-poly(n-butyl methacrylate) copolymer obtained by click chemistry by EPR and SS-NMR spectroscopies [J].
Borsacchi, Silvia ;
Calucci, Lucia ;
Geppi, Marco ;
La Terra, Federico ;
Pinzino, Calogero ;
Bertoldo, Monica .
CARBOHYDRATE POLYMERS, 2014, 112 :245-254
[3]  
Calmark A., 2009, CHEM SOC REV, V38, P352
[4]   A highly active and reusable copper(I)-tren catalyst for the "click'' 1,3-dipolar cycloaddition of azides and alkynes [J].
Candelon, Nicolas ;
Lastecoueres, Dominique ;
Diallo, Abdou Khadri ;
Aranzaes, Jaime Ruiz ;
Astruc, Didier ;
Vincent, Jean-Marc .
CHEMICAL COMMUNICATIONS, 2008, (06) :741-743
[5]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855
[6]   Fixed-charge labels for simplified reaction analysis: 5-hydroxy-1,2,3-triazoles as byproducts of a copper(I)-catalyzed click reaction [J].
Chen, Xingqiang ;
Khairallah, George N. ;
O'Hair, Richard A. J. ;
Williams, Spencer J. .
TETRAHEDRON LETTERS, 2011, 52 (21) :2750-2753
[7]   Synthesis and characterization of graft copolymers by photoinduced CuAAC click chemistry [J].
Demirci, Gulsah ;
Tasdelen, Mehmet Atilla .
EUROPEAN POLYMER JOURNAL, 2015, 66 :282-289
[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]   [(NHC)2Cu]X Complexes as Efficient Catalysts for Azide-Alkyne Click Chemistry at Low Catalyst Loadings [J].
Diez-Gonzalez, Silvia ;
Nolan, Steven P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (46) :8881-8884
[10]   'Click' cycloaddition catalysts: copper(I) and copper(II) tris(triazolylmethyl)amine complexes [J].
Donnelly, Paul S. ;
Zanatta, Shannon D. ;
Zammit, Steven C. ;
White, Jonathan M. ;
Williams, Spencer J. .
CHEMICAL COMMUNICATIONS, 2008, (21) :2459-2461