Direct route to well-defined poly(ionic liquid)s by controlled radical polymerization in water

Cordella, Daniela; Kermagoret, Anthony; Debuigne, Antoine; Riva, Raphaël; German, Ian; Isik, Mehmet; Jérôme, Christine; Meccereyes, David; Taton, Daniel; Detrembleur, Christophe

doi:10.1021/mz500721r

Request a copy

Article (Scientific journals)

Direct route to well-defined poly(ionic liquid)s by controlled radical polymerization in water

Cordella, Daniela; Kermagoret, Anthony; Debuigne, Antoine et al.

2014 • In ACS Macro Letters, 3, p. 1276-1280

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/174743

DOI
10.1021/mz500721r

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

Cordella D 2014 ACS Macro Lett 3,1276.pdf

Publisher postprint (702.73 kB)

Request a copy

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Keywords :

radical polymerization; cobalt-mediated radical polymerization (CMRP); ionic liquid

Abstract :

[en] The precision synthesis of poly(ionic liquid)s (PILs) in water is achieved for the first time by the cobalt-mediated radical polymerization (CMRP) of N-vinyl-3-alkylimidazolium-type monomers following two distinct protocols. The first involves the CMRP of various 1-vinyl-3-alkylimidazolium bromides conducted in water in the presence of an alkyl–cobalt(III) complex acting as a monocomponent initiator and mediating agent. Excellent control over molar mass and dispersity is achieved at 30 °C. Polymerizations are complete in a few hours, and PIL chain-end fidelity is demonstrated up to high monomer conversions. The second route uses the commercially available bis(acetylacetonato)cobalt(II) (Co(acac)2) in conjunction with a simple hydroperoxide initiator (tert-butyl hydroperoxide) at 30, 40, and 50 °C in water, facilitating the scaling-up of the technology. Both routes prove robust and straightforward, opening new perspectives onto the tailored synthesis of PILs under mild experimental conditions in water.

Research Center/Unit :

Center for Education and Research on Macromolecules (CERM)

Disciplines :

Materials science & engineering
Chemistry

Author, co-author :

Cordella, Daniela ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Kermagoret, Anthony ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Debuigne, Antoine ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Riva, Raphaël ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

German, Ian ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Isik, Mehmet; University of the Basque Country, Institute for Polymer Materials (POLYMAT), Spain

Jérôme, Christine ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie des macromolécules et des matériaux organiques (CERM)

Meccereyes, David; University of the Basque Country, Institute for Polymer Materials (POLYMAT), Spain

Taton, Daniel; University of Bordeaux, Laboratoire de Chimie des Polymères Organiques (LCPO), France

Detrembleur, Christophe ; University of Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Language :

English

Title :

Direct route to well-defined poly(ionic liquid)s by controlled radical polymerization in water

Publication date :

05 December 2014

Journal title :

ACS Macro Letters

eISSN :

2161-1653

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

Pages :

1276-1280

Peer reviewed :

Peer Reviewed verified by ORBi

European Projects :

FP7 - 256599 - RENAISSANCE - The Renaissance Project: Towards a strategic orientation and associated toolkit to support global UCD that is appropriate and accountable to local culture

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
CE - Commission Européenne [BE]

Available on ORBi :

since 08 December 2014

Statistics

Number of views

90 (19 by ULiège)

Number of downloads

1 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

(a) Green, O.; Grubjesic, S.; Lee, S.; Firestone, M. A. Polym. Rev. 2009, 49, 339.
(b) Mecerreyes, D. Prog. Polym. Sci. 2011, 36, 1629.
(c) Yuan, J.; Mecerreyes, D.; Antonietti, M. Prog. Polym. Sci. 2013, 38, 1009.
(d) Green, M. D.; Long, T. E. Polym. Rev. 2009, 49, 291.
(e) Schultz, A. R.; Lambert, P. M.; Chartrain, N. A.; Ruohoniemi, D. M.; Zhang, Z.; Jangu, C.; Zhang, M.; Williams, C. B.; Long, T. E. ACS Macro Lett. 2014, 3, 1205.
(f) Abdelhedi-Miladi, I.; Montarnal, D.; Obadia, M. M.; Ben Romdhane, H.; Drockenmuller, E. ACS Macro Lett. 2014, 3, 1187.
(g) Suga, T.; Sakata, M.; Aoki, K.; Nishide, H. ACS Macro Lett. 2014, 3, 703.
(h) Men, Y.; Schlaad, H.; Yuan, J. ACS Macro Lett. 2013, 2, 456.
(a) He, H.; Zhong, M.; Luebke, D.; Nulwala, H.; Matyjaszewski, K. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2175.
(b) Tang, H.; Tang, J.; Ding, S.; Radosz, M.; Shen, Y. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 1432.
(c) Nakamura, Y.; Nakanishi, K.; Yamago, S.; Tsujii, Y.; Takahashi, K.; Morinaga, T.; Sato, T. Macromol. Rapid Commun. 2014, 35, 642.
(d) He, H.; Luebke, D.; Nulwala, H.; Matyjaszewski, K. Macromolecules 2014, 47, 6601.
(a) Bara, J. E.; Lessmann, S.; Gabriel, C. J.; Hatakeyama, E. S.; Noble, R. D.; Gin, D. L. Ind. Eng. Chem. Res. 2007, 46, 5397.
(b) Ohno, H.; Yoshizawa, M.; Ogihara, W. Electrochim. Acta 2004, 50, 255.
(c) Marcilla, R.; Blazquez, J. A.; Rodriguez, J.; Pomposo, J. A.; Mecerreyes, D. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 208.
(d) Cardiano, P.; Mineo, P. G.; Neri, F.; Lo Schiavo, S.; Piraino, P. J. Mater. Chem. 2008, 18, 1253.
(a) Mudraboyina, B. P.; Obadia, M. M.; Allaoua, I.; Sood, R.; Serghei, A.; Drockenmuller, E. Chem. Mater. 2014, 26, 1720.
(b) Dimitrov-Raytchev, P.; Beghdadi, S.; Serghei, A.; Drockenmuller, E. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 34.
(a) Aitken, B. S.; Buitrago, C. F.; Heffley, J. D.; Lee, M.; Gibson, H. W.; Winey, K. I.; Wagener, K. B. Macromolecules 2012, 45, 681.
(b) Yuan, J.; Antonietti, M. Polymer 2011, 52, 1469.
(a) Stancik, C. M.; Lavoie, A. R.; Schuetz, J.; Achurra, P. A.; Lindner, P.; Gast, A. P.; Waymouth, R. M. Langmuir 2004, 20, 596.
(b) Stancik, C. M.; Lavoie, A. R.; Achurra, P. A.; Waymouth, R. M.; Gast, A. P. Langmuir 2004, 20, 8975.
(c) Mori, H.; Yahagi, M.; Endo, T. Macromolecules 2009, 42, 8082.
(d) Mori, H.; Ebina, Y.; Kambara, R.; Nakabayashi, K. Polym. J. 2012, 44, 550.
(e) Karjalainen, E.; Chenna, N.; Laurinmaeki, P.; Butcher, S. J.; Tenhu, H. Polym. Chem. 2013, 4, 1014.
(a) Green, M. D.; Choi, J.-H.; Winey, K. I.; Long, T. E. Macromolecules 2012, 45, 4749.
(b) Gao, R.; Wang, D.; Heflin, J. R.; Long, T. E. J. Mater. Chem. 2012, 22, 13473.
(c) Ye, Y.; Choi, J.-H.; Winey, K. I.; Elabd, Y. A. Macromolecules 2012, 45, 7027.
(d) Ye, Y.; Sharick, S.; Davis, E. M.; Winey, K. I.; Elabd, Y. A. ACS Macro Lett. 2013, 2, 575.
(e) Choi, J.-H.; Ye, Y.; Elabd, Y. A.; Winey, K. I. Macromolecules 2013, 46, 5290.
(f) Chanthad, C.; Masser, K. A.; Xu, K.; Runt, J.; Wang, Q. J. Mater. Chem. 2012, 22, 341.
(g) Schneider, Y.; Modestino, M. A.; McCulloch, B. L.; Hoarfrost, M. L.; Hess, R. W.; Segalman, R. A. Macromolecules 2013, 46, 1543.
(h) Weber, R. L.; Ye, Y.; Schmitt, A. L.; Banik, S. M.; Elabd, Y. A.; Mahanthappa, M. K. Macromolecules 2011, 44, 5727.
(i) Coupillaud, P.; Fèvre, M.; Wirotius, A.-L.; Aissou, K.; Fleury, G.; Debuigne, A.; Detrembleur, C.; Mecerreyes, D.; Vignolle, J.; Taton, D. Macromol. Rapid Commun. 2014, 35, 422.
(a) Vijayakrishna, K.; Jewrajka, S. K.; Ruiz, A.; Marcilla, R.; Pomposo, J. A.; Mecerreyes, D.; Taton, D.; Gnanou, Y. Macromolecules 2008, 41, 6299.
(b) Vijayakrishna, K.; Mecerreyes, D.; Gnanou, Y.; Taton, D. Macromolecules 2009, 42, 5167.
(a) Yuan, J.; Schlaad, H.; Giordano, C.; Antonietti, M. Eur. Polym. J. 2011, 47, 772.
(b) Moad, G.; Rizzardo, E.; Thang, S. H. Aust. J. Chem. 2009, 62, 1402.
Detrembleur, C.; Debuigne, A.; Hurtgen, M.; Jérôme, C.; Pinaud, J.; Fèvre, M.; Coupillaud, P.; Vignolle, J.; Taton, D. Macromolecules 2011, 44, 6397.
(a) Salamone, J. C.; Israel, S. C.; Taylor, P.; Snider, B. Polymer 1973, 14, 639.
(b) Yuan, J.; Antonietti, M. Macromolecules 2011, 44, 744.
(c) Men, Y.; Drechsler, M.; Yuan, J. Macromol. Rapid Commun. 2013, 34, 1721.
(a) Nicolas, J.; Charleux, B.; Guerret, O.; Magnet, S. Macromolecules 2004, 37, 4453.
(b) Nicolas, J.; Charleux, B.; Guerret, O.; Magnet, S. Angew. Chem., Int. Ed. 2004, 43, 6186.
(c) Charleux, B.; Nicolas, J. Polymer 2007, 48, 5813.
(d) Phan, T. N. T.; Bertin, D. Macromolecules 2008, 41, 1886.
(e) Nicolas, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B. Prog. Polym. Sci. 2013, 38, 63.
(f) Detrembleur, C.; Teyssié, P.; Jérôme, R. Macromolecules 2002, 35, 1611.
(a) Zhang, Q.; Wilson, P.; Li, Z.; McHale, R.; Godfrey, J.; Anastasaki, A.; Waldron, C.; Haddleton, D. M. J. Am. Chem. Soc. 2013, 135, 7355.
(b) Percec, V.; Popov, A. V.; Ramirez-Castillo, E.; Monteiro, M.; Barboiu, B.; Weichold, O.; Asandei, A. D.; Mitchell, C. M. J. Am. Chem. Soc. 2002, 124, 4940.
(c) Zhang, Q.; Wilson, P.; Anastasaki, A.; McHale, R.; Haddleton, D. M. ACS Macro Lett. 2014, 3, 491.
(a) Wang, X. S.; Lascelles, S. F.; Jackson, R. A.; Armes, S. P. Chem. Commun. 1999, 1817.
(b) Nishikawa, T.; Kamigaito, M.; Sawamoto, M. Macromolecules 1999, 32, 2204.
(c) Wang, X. S.; Armes, S. P. Macromolecules 2000, 33, 6640.
(d) Bortolamei, N.; Isse, A. A.; Magenau, A. J. D.; Gennaro, A.; Matyjaszewski, K. Angew. Chem., Int. Ed. 2011, 50, 11391.
(e) Konkolewicz, D.; Krys, P.; Góis, J. R.; Mendonc¸a, P. V.; Zhong, M.; Wang, Y.; Gennaro, A.; Isse, A. A.; Fantin, M.; Matyjaszewski, K. Macromolecules 2014, 47, 560.
(f) Texter, J.; Vasantha, V. A.; Crombez, R.; Maniglia, R.; Slater, L.; Mourey, T. Macromol. Rapid Commun. 2012, 33, 69.
(a) Lowe, A. B.; McCormick, C. L. Prog. Polym. Sci. 2007, 32, 283.
(b) Guinaudeau, A.; Coutelier, O.; Sandeau, A.; Mazieres, S.; Nguyen, T. H. D.; Le Drogo, V.; Wilson, D. J.; Destarac, M. Macromolecules 2014, 47, 41.
(c) Alidedeoglu, A. H.; York, A. W.; McCormick, C. L.; Morgan, S. E. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 5405.
(d) Chaduc, I.; Crepet, A.; Boyron, O.; Charleux, B.; D'Agosto, F.; Lansalot, M. Macromolecules 2013, 46, 6013.
(e) McCormick, C. L.; Lowe, A. B. Acc. Chem. Res. 2004, 37, 312.
(a) Peng, C.-H.; Fryd, M.; Wayland, B. B. Macromolecules 2007, 40, 6814.
(b) Debuigne, A.; Caille, J.-R.; Detrembleur, C.; Jerome, R. Angew. Chem., Int. Ed. 2005, 44, 3439.
(c) Detrembleur, C.; Debuigne, A.; Bryaskova, R.; Charleux, B.; Jerome, R. Macromol. Rapid Commun. 2006, 27, 37.
(a) Debuigne, A.; Champouret, Y.; Jerome, R.; Poli, R.; Detrembleur, C. Chem.-Eur. J. 2008, 14, 4046.
(b) Debuigne, A.; Poli, R.; Jerome, R.; Jerome, C.; Detrembleur, C. ACS Symp. Ser. 2009, 1024, 131.
(a) Bis(trifluorosulfonyl)imide (TFSI) anions were substituted for bromine anions (Br).
(b) He, H.; Zhong, M.; Adzima, B.; Luebke, D.; Nulwala, H.; Matyjaszewski, K. J. Am. Chem. Soc. 2013, 135, 4227.
(a) Debuigne, A.; Jerome, C.; Detrembleur, C. Angew. Chem., Int. Ed. 2009, 48, 1422.
(b) Kermagoret, A.; Debuigne, A.; Jérôme, C.; Detrembleur, C. Nat. Chem. 2014, 6, 179.
Bryaskova, R.; Detrembleur, C.; Debuigne, A.; Jerome, R. Macromolecules 2006, 39, 8263.