“One-pot” dispersion ATRP and alkyne-azide Huisgen’s 1,3-dipolar cycloaddition in supercritical carbon dioxide: towards the formation of functional microspheres
green technology; supercritical carbon dioxide; click chemistry; copper-mediated Huisgen's cycloaddition; radical polymerization; atom transfer radical polymerization (ATRP)
Abstract :
[en] Functional polymers were successfully prepared in scCO2 by combining alkyne-azide 1,3-dipolar Huisgen’s cycloaddition and dispersion ATRP in a “one pot” process using new perfluorinated polymeric amino-based ligands that had a dual role, i.e. the complexation of the copper catalyst and the stabilization of growing particles.
Research Center/Unit :
Center for Education and Researchon Macromolecules (CERM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Grignard, Bruno ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Calberg, Cédric ; Université de Liège - ULiège > Department of Applied Chemistry > Laboratory of Industrial Chemistry
Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Detrembleur, Christophe ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
“One-pot” dispersion ATRP and alkyne-azide Huisgen’s 1,3-dipolar cycloaddition in supercritical carbon dioxide: towards the formation of functional microspheres
Publication date :
June 2010
Journal title :
Journal of Supercritical Fluids
ISSN :
0896-8446
Publisher :
Elsevier Science, Amsterdam, Netherlands
Volume :
53
Issue :
1-3
Pages :
151-155
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique F.R.S.-FNRS - Fonds de la Recherche Scientifique The “Région Wallonne” and the FEDER in the frame of the POLYTISS program
Matyjaszewski K., and Xia J. Atom transfer radical polymerization. Chemical Review 101 (2001) 2921-2990
Tsarevsky N., and Matyjaszewski K. "Green" atom transfer radical polymerization: from process design to preparation of well-defined environmentally friendly polymeric materials. Chemical Review 107 (2007) 2270-2299
Gao H., and Matyjaszewski K. Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: from stars to gels. Progress in Polymer Science 34 4 (2009) 317-350
Matyjaszewski K., and Tsarevsky N.V. Nanostructured functional materials prepared by atom transfer radical polymerization. Nature Chemistry 1 4 (2009) 276-288
Tornøe C.W., Christensen C., and Meldal M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. Journal of Organic Chemistry 67 (2002) 3057-3064
Rostovstev V.V., Green L.G., Fokin V.V., and Sharpless K.B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angewandte Chemie International Edition 41 (2002) 2596-2599
Gondi S.R., Vogt A.P., and Sumerlin B.S. Versatile pathway to functional telechelics via RAFT polymerization and click chemistry. Macromolecules 40 (2007) 474-481
Lutz J.-F., Boerner G.H., and Weichenhan K. Combining ATRP and "Click" chemistry: a promising platform toward functional biocompatible polymers and polymer bioconjugates. Macromolecules 39 (2006) 6376-6383
Lutz J.-F., Boerner G.H., and Weichenhan K. Combining atom transfer radical polymerization and click chemistry: a versatile method for the preparation of end-functional polymers. Macromolecular Rapid Communications 26 (2005) 514-518
Riva R., Schmeits S., Jerome C., Jerome R., and Lecomte Ph. Combination of ring-opening polymerization and "Click Chemistry": toward functionalization and grafting of polycaprolactone. Macromolecules 40 (2007) 796-803
Lecomte Ph., Riva R., Jerome C., and Jerome R. Macromolecular engineering of biodegradable polyesters by ring-opening polymerization and 'click' chemistry. Macromolecular Rapid Communications 29 (2008) 982-997
Egede D.A., Hvilsted S., Thomas S., and Larsen N.B. Conductive polymer functionalization by click chemistry. Macromolecules 41 (2008) 4321-4327
Binder W.H., and Sachsenhofer R. 'Click' chemistry in polymer and material science: an update. Macromolecular Rapid Communications 29 (2008) 952-981
Wiltshire J.T., and Qiao G.G. Degradable star polymers with high "click" functionality. Journal of Polymer Science, Part A: Polymer Chemistry 47 6 (2009) 1485-1498
Sinnwell S., Lammens M., Stenzel M.H., Du Prez F.E., and Barner-Kowollik F.C. Efficient access to multi-arm star block copolymers by a combination of ATRP and RAFT-HDA click chemistry. Journal of Polymer Science, Part A: Polymer Chemistry 47 8 (2009) 2207-2213
Damiron D., Desorme M., Ostaci R.-V., Al Akhrass S., Hamaide T., and Drockenmuller E. Functionalized random copolymers from versatile one-pot click chemistry/ATRP tandems approaches. Journal of Polymer Science, Part A: Polymer Chemistry 47 15 (2009) 3803-3813
Zhang Y., He H., and Gao C. Clickable macroinitiator strategy to build amphiphilic polymer brushes on carbon nanotubes. Macromolecules 41 24 (2008) 9581-9594
Fleischmann S., Komber H., Appelhans D., and Voit B. Synthesis of functionalized NMP initiators for click chemistry: a versatile method for the preparation of functionalized polymers and block copolymers. Macromolecular Chemistry and Physics 208 (2007) 1050-1060
Mayo J.D., Behal S., and Adronov A. Phase separation of polymer-functionalized SWNTs within a PMMA/polystyrene blend. Journal of Polymer Science, Part A: Polymer Chemistry 47 (2009) 450-458
Geng J., Lindqvist J., Mantovani G., and Haddleton D.M. Simultaneous copper(I)-catalyzed azide - alkyne cycloaddition (CuAAC) and living radical polymerization. Angewandte Chemie International Edition 47 (2008) 4180-4183
Huang C.-J., and Chang F.-C. Using click chemistry to fabricate ultrathin thermoresponsive microcapsules through direct covalent layer-by-layer assembly. Macromolecules 42 14 (2009) 5155-5166
Tsarevsky N.V., Sumerlin B.S., and Matyjaszewski K. Step-growth "click" coupling of telechelic polymers prepared by atom transfer radical polymerisation. Macromolecules 38 (2005) 3558-3561
Mespouille L., Vachaudez M., Suriano F., Gerbaux P., Coulembier O., Degee Ph., Flammang R., and Dubois Ph. One-pot synthesis of well-defined amphiphilic and adaptative block copolymers via versatile combination of "click" chemistry and ATRP. Macromolecular Rapid Communications 28 (2007) 2151-2158
Zetterlund P.B., Aldabbagh F., and Okubo M. Controlled/living heterogeneous radical polymerization in supercritical carbon dioxide. Journal of Polymer Science, Part A: Polymer Chemistry 47 (2009) 3711-3728
Thurecht K.J., and Howdle S.M. Controlled dispersion polymerization in supercritical carbon dioxide. Australian Journal of Chemistry 62 8 (2009) 786-789
Xia J., Johnson T., Gaynor S.G., Matyjaszewski K., and DeSimone J. Atom transfer radical polymerization in supercritical carbon dioxide. Macromolecules 32 (1999) 4802-4804
Villarroya S., Zhou J., Duxbury C.J., Heise A., and Howdle S.M. Synthesis of semifluorinated block copolymers containing poly(caprolactone) by the combination of ATRP and enzymatic ROP in scCO2. Macromolecules 39 (2006) 633-640
Zhou J., Villarroya S., Wang W., Wyatt M.F., Duxbury C.J., Thurecht K.J., and Howdle S.M. One-step chemoenzymatic synthesis of poly(caprolactone-block-methyl methacrylate) in supercritical CO2. Macromolecules 39 16 (2006) 5352-5358
Villarroya S., Zhou J., Thurecht K.J., and Howdle S.M. Synthesis of graft copolymers by the combination of ATRP and enzymatic ROP in scCO2. Macromolecules 39 (2006) 9080-9086
Minami H., Kagawa Y., Kuwahara S., Fujii S., and Okubo M. Dispersion atom transfer radical polymerization of methyl methacrylate with bromo-terminated poly(dimethylsiloxane) in supercritical carbon dioxide. Designed Monomers and Polymers 7 (2004) 553-562
Grignard B., Jerome C., Calberg C., Jerome R., Wang W., Howdle S.M., and Detrembleur C. Dispersion ATRP of vinyl monomers in supercritical carbon dioxide. Macromolecules 41 (2008) 8575-8583
Grignard B., Jerome C., Calberg C., Jerome R., Wang W., Howdle S.M., and Detrembleur C. Copper bromide complexed by fluorinated macro-ligands: towards microspheres by ATRP of vinyl monomers in scCO2. Chemical Communications 3 (2008) 314-316
Grignard B., Jerome C., Calberg C., Jerome R., and Detrembleur C. Atom transfer radical polymerization of MMA with a macromolecular ligand in a fluorinated solvent and in supercritical carbon dioxide. European Polymer Journal 44 (2008) 861-871
Grignard B., Jerome C., Calberg C., Wang W., Howdle S.M., and Detrembleur C. Supported ATRP of fluorinated methacrylates in supercritical carbon dioxide: preparation of scCO2 soluble polymers with low catalytic residues. Chemical Communications 44 (2008) 5803
Scholz H.A. History of water-thinned paints. Journal of Industrial and Engineering Chemistry 45 (1953) 710-711
Jenkins P.G., Howard K.A., Blackhall N.W., Thomas N.W., Davis S.S., and Ohagan D.T. Microparticulate absorption from the rat intestine. Journal of Controlled Release 29 (1994) 339-350
Rouilly A., Rigal L., and Gilbert R.G. Synthesis and properties of composites of starch and chemically modified natural rubber. Polymer 45 (2004) 7813-7820
Breed D.R., Thibault R., Xie F., Wang Q., Hawker C.J., and Pine D.J. Functionalization of polymer microspheres using click chemistry. Langmuir 25 (2009) 4370-4376
Chen G., Tao L., Mantovani G., Ladmiral V., Burt D.P., Macpherson J.V., and Haddleton D.M. Synthesis of azide/alkyne-terminal polymers and application for surface functionalization through a [2 + 3] Huisgen cycloaddition process, "click chemistry". Soft Matter 3 (2007) 732-739