Modulating catalytic activity of polymer-based cuAAC "click" reactions

Bell, Craig A., Jia, Zhongfan, Perrier, Sebastien and Monteiro, Michael J. (2011) Modulating catalytic activity of polymer-based cuAAC "click" reactions. Journal of Polymer Science Part A-Polymer Chemistry, 49 21: 4539-4548. doi:10.1002/pola.24896

Author Bell, Craig A.
Jia, Zhongfan
Perrier, Sebastien
Monteiro, Michael J.
Title Modulating catalytic activity of polymer-based cuAAC "click" reactions
Journal name Journal of Polymer Science Part A-Polymer Chemistry   Check publisher's open access policy
ISSN 0887-624X
Publication date 2011-11-01
Year available 2011
Sub-type Article (original research)
DOI 10.1002/pola.24896
Volume 49
Issue 21
Start page 4539
End page 4548
Total pages 10
Place of publication Hoboken, NJ, United States
Publisher John Wiley & Sons
Language eng
Formatted abstract
The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction is used to synthesize complex polymer architectures. In this work, we demonstrate the control of this reaction at 25°C between polystyrene (PSTY) chains through modulating the catalytic activity by varying the combinations of copper source (i.e., Cu(I)Br or copper wire), ligand (PMDETA and/or triazole ligand), and solvent (toluene or DMF). The fastest rate of CuAAC was found using Cu(I)Br/PMDETA ligand in toluene, reaching near full conversion after 15 min at 25°C. For the same catalysts system, DMF also gave fast rates of ‘‘click" (95% conversion in 25 min). Cu(0) wire in toluene gave a conversion of 98% after 600 min, a much higher rate than that observed for the same catalyst system used in DMF. When the PSTY had a chemically bound triazole ring close to the site of reaction, the rate of CuAAC in toluene increased significantly, 97% in 180 min at 25°C, in agreement with our previously published results. This suggests that rapid rates can be obtained using copper wire and will have direct applications to
the synthesis of compound where air, removal of copper, and reuse of the copper catalyst are required.
Keyword "click" chemistry
diblock copolymers
living radical polymerization (LRP)
Transfer Radical Polymerization
Azide-Alkyne Cycloaddition
Selective Degradable Linkages
Efficient Route
Q-Index Code C1
Q-Index Status Confirmed Code
Grant ID DP0987315
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2012 Collection
Australian Institute for Bioengineering and Nanotechnology Publications
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