Graft block copolymers of propargyl methacrylate and vinyl acetate via a combination of RAFT/MADIX and click chemistry: Reaction analysis

Quémener, D., Le Hellaye, M., Bissett, C., Davis, T. P., Barner-Kowollik, C., & Stenzel, M. H. (2008) Graft block copolymers of propargyl methacrylate and vinyl acetate via a combination of RAFT/MADIX and click chemistry: Reaction analysis. Journal of Polymer Science, Part A: Polymer Chemistry, 46(1).

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Propargyl methacrylate with its acetylene function protected with a silyl group is polymerized via the reversible addition fragmentation chain transfer (RAFT) process, using cyanoisopropyl dithiobenzoate (CPDB) as RAFT agent, and subsequently deprotected to afford a polymer backbone where each repeated unit is decorated with an acetylene functionality (1000 < Mn < 13,600 g mol-1, 1.07 < PDI < 1.29). In parallel, an azide functionalized xanthate (ethoxythiocarbonylsulfanyl-acetic acid 3-azido-propyl ester) was employed to prepare narrow polydisperse poly(vinyl acetate) (M n = 850 g mol-1, PDI = 1.20). The two polymers are conjugated by Huisgen 1,3-dipolar cycloaddition to afford narrow polydisperse comb polymer (1.12 < PDI < 1.18, 3400 < Mn < 12,500 g mol-1, based on linear polystyrene calibration, 4500 < M n theo < 15,600 g mol-1). The study places special emphasis on following the copper catalyzed 1,3-dipolar cycloaddition via Fourier Transform Infrared Spectroscopy (FTIR) as well as via on-line UV-Vis photospectrometry on several model compounds, i.e. the nonmonomer inserted azido-xanthate RAFT/MADLX. agent as well as a 2-propargyl-2-bromopropionate and 3-azidopropyl-2-bromopropionate model compounds. A suitable absorption band in the VIS at 666 nm (tentatively assigned to a charge transfer complex between copper(I) and the forming triazole moieties) is identified as a promising sensor for following the click reaction kinetics, thus allowing for the rapid assessment of reaction completion in an on-line fashion. © 2007 Wiley Periodicals, Inc.

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ID Code: 99191
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :75 Export Date: 5 September 2016 CODEN: JPACE Correspondence Address: Barner-Kowollik, C.; Centre for Advanced Macromolecular Design, School of Chemical Sciences and Engineering, University of New South Wales, Sydney, NSW 2052, Australia; email: References: Chiellini, E., Corti, A., Antone, D', S., Solaro, R., (2003) Prog Polym Sci, 28, p. 963; Orienti, I., Di Pietra, A., Luppi, B., Zecchi, V., (2000) Arch Pharm Pharm Med Chem, 333, p. 421; Rump, A.F.E., Woschee, U., Theisohn, M., Fischbach, R., Heindel, W., Lackner, K., Klaus, W., (2002) Eur J Clin Pharmacol, 58, p. 459; Nagano, K., Yamane, S., Toyoschima, K., (1970) Polyvinyl Alcohol, , Kobunshi Kankokai: Tokyo; Roychoudhury, R., Kühn, S., Schott, H., Kössel, H., (1975) FEBS Lett, 50, p. 140; Merrill, E. W. 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Keywords: Graft copolymers, Huisgen 1,3-dipolar cycloaddition, Reversible addition fragmentation chain transfer (RAFT), UV-vis spectroscopy, Acetic acid, Acetylene, Fourier transform infrared spectroscopy, Reaction kinetics, Ultraviolet spectroscopy, Photospectrometry
DOI: 10.1002/pola.22367
ISSN: 0887624X
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 10 Oct 2016 04:20

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