Wallyn, Sofie, Lammens, Mieke, O'Reilly, Rachel K. and Prez, Filip Du. (2011) Highly active, thermo-responsive polymeric catalytic system for reuse in aqueous and organic CuAAC reactions. Journal of Polymer Science Part A: Polymer Chemistry, Vol.49 (No.13). pp. 2878-2885. ISSN 0887-624X

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Abstract

Tris-(benzyltriazolylmethyl)amine (TBTA) has been immobilized onto a styrenic monomer and subsequently copolymerized with N-isopropyl acrylamide (NIPAM) to afford catalytically active thermo-responsive copolymers for copper assisted click chemistry. P(TBTA-co-NIPAM) copolymers were synthesized with incorporation of between 2 and 10 ligand units per chain and tuneable molecular weight (28–148 kDa). A combination of 1H NMR spectroscopy, size exclusion chromatography (SEC) and elemental analysis (EA) confirmed the controlled synthesis of these polymers and allowed for quantification of the degree of TBTA-functionalized monomer incorporation. After loading with copper(I) bromide, this homogeneous catalyst system was added to a water/ethyl acetate two-phase system. Using this biphasic system aqueous click reactions could be performed at room temperature, while organic click chemistry could be performed above the cloud point temperature of the catalyst system. The polymer catalyst system could be regenerated via extraction by making use of its lower critical solution temperature (LCST)-behavior, and then reused for further copper(I) catalyzed azide-alkyne cycloaddition (CuAAC) reactions. While a reduced catalytic activity is observed as a result of copper leaching in aqueous click reactions, the recycling experiments in the organic phase demonstrated that this copolymer supported system allows for efficient recycling and reuse. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Polymerization, Polymers, Catalysts, Monomers, Chemical reactions
Journal or Publication Title:	Journal of Polymer Science Part A: Polymer Chemistry
Publisher:	John Wiley & Sons Ltd.
ISSN:	0887-624X
Date:	2011
Volume:	Vol.49
Number:	No.13
Page Range:	pp. 2878-2885
Identification Number:	10.1002/pola.24723
Status:	Peer Reviewed
Publication Status:	Published
Funder:	Belgian Program on Interuniversity Attraction Poles (IAP), Royal Society (Great Britain), Engineering and Physical Sciences Research Council (EPSRC), University of Cambridge
References:	1 Barner-Kowollik, C.; Perrier, S. J Polym Sci Part A: Polym Chem 2008, 46, 5715–5723. 2 Moad, G.; Rizzardo, E.; Thang, S. H. Aust J Chem 2006, 59, 669–692. 3 Moad, G.; Rizzardo, E.; Thang, S. H. Aust J Chem 2009, 62, 1402–1472. 4 Loos, W.; Du Prez, F. Macromol Symp 2004, 210, 483–491. 5 Heskins, M.; Guillet, J. E. J Macromol Sci Chem 1968, 2, 1441–1455. 6 Plate, N. A.; Lebedeva, T. L.; Valuev, L. I. Polym J 1999, 31, 21–27. 7 Yin, X.; Hoffman, A. S.; Stayton, P. S. Biomacromolecules 2006, 7, 1381–1385. 8 McGrath, J. G.; Bock, R. D.; Cathcart, J. M.; Lyon, L. A. Chem Mat 2007, 19, 1584–1591. 9 Li, P.; Zhu, A. M.; Liu, Q. L.; Zhang, Q. G. Ind Eng Chem Res 2008, 47, 7700–7706. 10 Brugger, B.; Richtering, W. Adv Mater 2007, 19, 2973– 2978. 11 Shiroya, T.; Yasui, M.; Fujimoto, K.; Kawaguchi, H. Colloids Surf B 1995, 4, 275–285. 12 Chen, J. P.; Hoffman, A. S. Biomaterials 1990, 11, 631–634. 13 Takei, Y. G.; Aoki, T.; Sanui, K.; Ogata, N.; Okano, T.; Sakurai, Y. Bioconjugate Chem 1993, 4, 341–346. 14 Takei, Y. G.; Aoki, T.; Sanui, K.; Ogata, N.; Okano, T.; Sakurai, Y. Bioconjugate Chem 1993, 4, 42–46. 15 Bergbreiter, D. E.; Case, B. L.; Liu, Y.-S.; Caraway, J. W. Macromolecules 1998, 31, 6053–6062. 16 Bergbreiter, D. E.; Hamilton, P. N.; Koshti, N. M. J Am Chem Soc 2007, 129, 10666–10667. 17 Iha, R. K.; Wooley, K. L.; Nystro¨ m, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem Rev 2009, 109, 5620–5686. 18 Lammens, M.; Skey, J.; Wallyn, S.; O’Reilly, R.; Du Prez, F. Chem Commun 2010, 46, 8719–8721. 19 Kurisawa, M.; Yokoyama, M.; Okano, T. J Controlled Release 2000, 68, 1–8. 20 Binauld, S.; Fleury, E.; Drockenmuller, E. J Polym Sci Part A: Polym Chem 2010, 48, 2470–2476. 21 Bonami, L.; Van Camp, W.; Van Rijckegem, D.; Du Prez, F. E. Macromol Rapid Commun 2009, 30, 34–38. 22 Chan, T. R.; Fokin, V. V. QSAR Comb Sci 2007, 26, 1274–1279. 23 Skey, J.; O’Reilly, R. K. Chem Commun 2008, 4183–4185.
URI:	http://wrap.warwick.ac.uk/id/eprint/40496

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