[en] Access to well-defined polymers made of the so-called ‘Less Activated Monomers’ (LAMs) via controlled radical polymerization has long been a challenge due to the lack of radical stabilizing group on the double bond of these monomers. This Feature Article summarizes substantial progress in the organometallic-mediated radical polymerization (OMRP) of this important class of monomers including vinyl esters, olefins, vinyl chloride, vinyl amides, or ionic-liquid vinyl monomers. It aims to provide a clear and comprehensive account of the fundamentals and challenges in the OMRP of LAMs as well as an overview of the resulting macromolecular engineering opportunities. The input of photochemistry, environmentally friendly solvents or flow reactors in OMRP is also presented. Finally, it emphasizes how some well-defined LAMs-based materials contributed to the development of specific applications notably in the fields of biomedicine or energy.
Research center :
Center for Education and Research on Macromolecules (CERM) CESAM Complex and Entangled Systems from Atoms to Materials (CESAM)
Disciplines :
Materials science & engineering Chemistry
Author, co-author :
Debuigne, Antoine ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Jérôme, Christine ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Detrembleur, Christophe ; University of Liège - ULiège > Complex and Entangled Systems from Atoms to Materials (CESAM), Center for Education and Research on Macromolecules (CERM)
Language :
English
Title :
Organometallic-mediated radical polymerization of 'less activated monomers': fundamentals, challenges and opportunities
Publication date :
21 April 2017
Journal title :
Polymer
ISSN :
0032-3861
eISSN :
1873-2291
Publisher :
Elsevier Science, Oxford, United Kingdom
Volume :
115
Pages :
285-307
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
[1] Lutz, J.-F., Ouchi, M., Liu, D.R., Sawamoto, M., Sequence-controlled polymers. Science, 80(341), 2013, 1238149, 10.1126/science.1238149.
[2] Badi, N., Lutz, J.-F., Sequence control in polymer synthesis. Chem. Soc. Rev. 38 (2009), 3383–3390, 10.1039/B806413J.
[3] Hibi, Y., Ouchi, M., Sawamoto, M., A strategy for sequence control in vinyl polymers via iterative controlled radical cyclization. Nat. Commun., 7, 2016, 11064, 10.1038/ncomms11064.
[4] Matyjaszewski, K., Tsarevsky, N.V., Macromolecular engineering by atom transfer radical polymerization. J. Am. Chem. Soc. 136 (2014), 6513–6533, 10.1021/ja408069v.
[5] Ouchi, M., Terashima, T., Sawamoto, M., Transition metal-catalyzed living radical polymerization: toward perfection in catalysis and precision polymer synthesis. Chem. Rev. 109 (2009), 4963–5050, 10.1021/cr900234b.
[6] Matyjaszewski, K., Xia, J., Atom transfer radical polymerization. Chem. Rev. 101 (2001), 2921–2990, 10.1021/cr940534g.
[7] Kamigaito, M., Ando, T., Sawamoto, M., Metal-catalyzed living radical polymerization. Chem. Rev. 101 (2001), 3689–3746, 10.1021/cr9901182.
[8] Rosen, B.M., Percec, V., Single-electron transfer and single-electron transfer degenerative chain transfer living radical polymerization. Chem. Rev. 109 (2009), 5069–5119, 10.1021/cr900024j.
[9] Hill, M.R., Carmean, R.N., Sumerlin, B.S., Expanding the scope of RAFT polymerization: recent advances and new horizons. Macromolecules 48 (2015), 5459–5469, 10.1021/acs.macromol.5b00342.
[10] Moad, G., Rizzardo, E., Thang, S.H., Radical addition–fragmentation chemistry in polymer synthesis. Polymer 49 (2008), 1079–1131 http://dx.doi.org/10.1016/j.polymer.2007.11.020.
[11] Hawker, C.J., Bosman, A.W., Harth, E., New polymer synthesis by nitroxide mediated living radical polymerizations. Chem. Rev. 101 (2001), 3661–3688, 10.1021/cr990119u.
[14] David, G., Boyer, C., Tonnar, J., Ameduri, B., Lacroix-Desmazes, P., Boutevin, B., Use of iodocompounds in radical polymerization. Chem. Rev. 106 (2006), 3936–3962, 10.1021/cr0509612.
[15] Yamago, S., Precision polymer synthesis by degenerative transfer controlled/living radical polymerization using organotellurium, organostibine, and organobismuthine chain-transfer agents. Chem. Rev. 109 (2009), 5051–5068, 10.1021/cr9001269.
[16] Hurtgen, M., Detrembleur, C., Jerome, C., Debuigne, A., Insight into organometallic-mediated radical polymerization. Polym. Rev. 51 (2011), 188–213.
[17] Poli, R., Relationship between One-electron Transition-metal Reactivity and Radical Polymerization Processes. Angew. Chemie Int. Ed 45 (2006), 5058–5070, 10.1002/anie.200503785.
[18] Poli, R., New phenomena in organometallic-mediated radical polymerization (OMRP) and perspectives for control of less active monomers. Chem. - A Eur. J. 21 (2015), 6988–7001, 10.1002/chem.201500015.
[23] Debuigne, A., Caille, J.-R., Jerome, R., Highly Efficient Cobalt-mediated Radical Polymerization of Vinyl Acetate. Angew. Chem., Int. Ed. 44 (2005), 1101–1104, 10.1002/anie.200461333.
[24] Debuigne, A., Champouret, Y., Jerome, R., Poli, R., Detrembleur, C., Mechanistic insights into the cobalt-mediated radical polymerization (CMRP) of vinyl acetate with cobalt(III) adducts as initiators. Chem. - Eur. J. 14 (2008), 4046–4059, 10.1002/chem.200701867.
[25] Maria, S., Kaneyoshi, H., Matyjaszewski, K., Poli, R., Effect of electron donors on the radical polymerization of vinyl acetate mediated by [Co(acac)2]: degenerative transfer versus reversible homolytic cleavage of an organocobalt(III) complex. Chem. - A Eur. J. 13 (2007), 2480–2492, 10.1002/chem.200601457.
[26] Debuigne, A., Poli, R., Jerome, R., Jerome, C., Detrembleur, C., Key role of metal-coordination in cobalt-mediated radical polymerization of vinyl acetate. ACS Symp. Ser. 1024 (2009), 131–147, 10.1021/bk-2009-1024.ch009.
[27] Wayland, B.B., Peng, C.-H., Fu, X., Lu, Z., Fryd, M., Degenerative transfer and reversible termination mechanisms for living radical polymerizations mediated by cobalt porphyrins. Macromolecules 39 (2006), 8219–8222, 10.1021/ma061643n.
[28] Wang, F.-S., Yang, T.-Y., Hsu, C.-C., Chen, Y.-J., Li, M.-H., Hsu, Y.-J., Chuang, M.-C., Peng, C.-H., The mechanism and thermodynamic studies of CMRP: different control mechanisms demonstrated by Co II (TMP), Co II (salen*), and Co II (acac) 2 mediated polymerization, and the correlation of reduction potential, equilibrium constant, and control mechanism. Macromol. Chem. Phys. 217 (2016), 422–432, 10.1002/macp.201500311.
[29] Le Grognec, E., Claverie, J., Poli, R., Radical polymerization of styrene controlled by half-sandwich Mo(III)/Mo(IV) couples: all basic mechanisms are possible. J. Am. Chem. Soc. 123 (2001), 9513–9524, 10.1021/ja010998d.
[30] Stoffelbach, F., Poli, R., Richard, P., Half-sandwich molybdenum(III) compounds containing diazadiene ligands and their use in the controlled radical polymerization of styrene. J. Organomet. Chem. 663 (2002), 269–276, 10.1016/S0022-328X(02)01878-8.
[31] Maria, S., Stoffelbach, F., Mata, J., Daran, J.-C., Richard, P., Poli, R., The radical trap in atom transfer radical polymerization need not Be thermodynamically stable. A study of the MoX 3 (PMe 3 ) 3 catalysts. J. Am. Chem. Soc. 127 (2005), 5946–5956, 10.1021/ja043078e.
[32] Stoffelbach, F., Poli, R., Maria, S., Richard, P., How the interplay of different control mechanisms affects the initiator efficiency factor in controlled radical polymerization: an investigation using organometallic MoIII-based catalysts. J. Organomet. Chem. 692 (2007), 3133–3143, 10.1016/j.jorganchem.2006.11.031.
[33] Braunecker, W.A., Brown, W.C., Morelli, B.C., Tang, W., Poli, R., Matyjaszewski, K., Origin of activity in Cu-, Ru-, and Os-Mediated radical polymerization. Macromolecules 40 (2007), 8576–8585, 10.1021/ma702008v.
[38] Shaver, M.P., Allan, L.E.N., Gibson, V.C., Organometallic intermediates in the controlled radical polymerization of styrene by α-Diimine iron catalysts. Organometallics 26 (2007), 4725–4730, 10.1021/om700395h.
[39] Allan, L.E.N., MacDonald, J.P., Nichol, G.S., Shaver, M.P., Single component iron catalysts for atom transfer and organometallic mediated radical polymerizations: mechanistic studies and reaction scope. Macromolecules 47 (2014), 1249–1257, 10.1021/ma402381x.
[41] Grishin, D.F., Ignatov, S.K., Shchepalov, A.A., Razuvaev, A.G., Mechanism of the controlled radical polymerization of styrene and methyl methacrylate in the presence of dicyclopentadienyltitanium dichloride. Appl. Organomet. Chem. 18 (2004), 271–276, 10.1002/aoc.631.
[42] Asandei, A.D., Moran, I.W., TiCp 2 Cl-Catalyzed living radical polymerization of styrene initiated by oxirane radical ring opening. J. Am. Chem. Soc. 126 (2004), 15932–15933, 10.1021/ja046936f.
[43] Asandei, A.D., Moran, I.W., The ligand effect in Ti-mediated living radical styrene polymerizations initiated by epoxide radical ring opening. 1. Alkoxide and bisketonate Ti complexes. J. Polym. Sci. Part A Polym. Chem. 43 (2005), 6028–6038, 10.1002/pola.20972.
[44] Asandei, A.D., Moran, I.W., The ligand effect in Ti-mediated living radical styrene polymerizations initiated by epoxide radical ring opening. 2. Scorpionate and half-sandwich LTiCl3 complexes. J. Polym. Sci. Part A Polym. Chem. 43 (2005), 6039–6047, 10.1002/pola.20970.
[45] Asandei, A.D., Saha, G., Cp2TiCl-catalyzed living radical polymerization of styrene initiated from peroxides. J. Polym. Sci. Part A Polym. Chem. 44 (2006), 1106–1116, 10.1002/pola.21206.
[46] Asandei, A.D., Moran, I.W., Saha, G., Chen, Y., Titanium-mediated living radical styrene polymerizations. VI. Cp2TiCl-catalyzed initiation by epoxide radical ring opening: effect of the reducing agents, temperature, and titanium/epoxide and titanium/zinc ratios. J. Polym. Sci. Part A Polym. Chem. 44 (2006), 2156–2165, 10.1002/pola.21326.
[47] Asandei, A.D., Moran, I.W., Saha, G., Chen, Y., Titanium-mediated living radical styrene polymerizations. V. Cp2TiCl-catalyzed initiation by epoxide radical ring opening: effect of solvents and additives. J. Polym. Sci. Part A Polym. Chem. 44 (2006), 2015–2026, 10.1002/pola.21307.
[48] Asandei, A.D., Moran, I.W., Ligand effect in Ti-mediated living radical styrene polymerizations initiated by epoxide radical ring opening. III. Substituted sandwich metallocenes. J. Polym. Sci. Part A Polym. Chem. 44 (2006), 1060–1070, 10.1002/pola.21220.
[49] Asandei, A.D., Chen, Y., Cp 2 TiCl-catalyzed SET reduction of aldehydes: a new initiating protocol for living radical polymerization. Macromolecules 39 (2006), 7549–7554, 10.1021/ma0604791.
[50] Asandei, A.D., Chen, Y., Saha, G., Moran, I.W., Cp2TiCl-catalyzed radical chemistry: living styrene polymerizations from epoxides, aldehydes, halides, and peroxides. Tetrahedron 64 (2008), 11831–11838, 10.1016/j.tet.2008.08.106.
[51] A.D. Asandei, C.P. Simpson, H.S. Yu, O.I. Adebolu, G. Saha, Y. Chen, Cp 2 TiCl-mediated controlled radical polymerization of isoprene initiated by epoxide radical ring opening, ACS Symp. Ser., Control. Radic. Polym. Prog. RAFT, DT, NMP OMRP. (2009) 149–163. http://dx.doi.org/10.1021/bk-2009-1024.ch010.
[52] Asandei, A.D., Saha, G., Cp 2 TiCl-catalyzed epoxide radical ring opening: a new initiating methodology for graft copolymer synthesis. Macromolecules 39 (2006), 8999–9009, 10.1021/ma0618833.
[53] Champouret, Y., Baisch, U., Poli, R., Tang, L., Conway, J.L., Smith, K.M., Homolytic Bond Strengths and Formation Rates in Half-Sandwich Chromium Alkyl Complexes: Relevance for Controlled Radical Polymerization. Angew. Chemie Int. Ed. 47 (2008), 6069–6072, 10.1002/anie.200801498.
[54] Champouret, Y., MacLeod, K.C., Baisch, U., Patrick, B.O., Smith, K.M., Poli, R., Cyclopentadienyl chromium β-diketiminate complexes: initiators, ligand steric effects, and deactivation processes in the controlled radical polymerization of vinyl acetate. Organometallics 29 (2010), 167–176, 10.1021/om900869p.
[56] Poli, R., Shaver, M.P., Atom transfer radical polymerization (ATRP) and organometallic mediated radical polymerization (OMRP) of styrene mediated by Diaminobis(phenolato)iron(II) complexes: a DFT study. Inorg. Chem. 53 (2014), 7580–7590, 10.1021/ic5009347.
[57] Xue, Z., Poli, R., Organometallic mediated radical polymerization of vinyl acetate with Fe(acac)2. J. Polym. Sci. Part A Polym. Chem. 51 (2013), 3494–3504, 10.1002/pola.26751.
[58] Leblanc, A., Grau, E., Broyer, J.-P., Boisson, C., Spitz, R., Monteil, V., Homo- and copolymerizations of (Meth)Acrylates with olefins (styrene, ethylene) using Neutral Nickel complexes: a dual radical/catalytic pathway. Macromolecules 44 (2011), 3293–3301, 10.1021/ma200158n.
[59] Debuigne, A., Poli, R., Jérôme, C., Jérôme, R., Detrembleur, C., Overview of cobalt-mediated radical polymerization: roots, state of the art and future prospects. Prog. Polym. Sci. 34 (2009), 211–239.
[60] Peng, C.-H., Li, S., Wayland, B.B., Aspects of living radical polymerization mediated by cobalt porphyrin complexes. J. Chin. Chem. Soc. 56 (2009), 219–233, 10.1002/jccs.200900032.
[61] Debuigne, A., Jerome, R., Jerome, C., Detrembleur, C., Cobalt-mediated Radical Polymerization. 2012, Wiley-VCH Verlag GmbH & Co. KGaA.
[63] Woska, D.C., Xie, Z.D., Gridnev, A.A., Ittel, S.D., Fryd, M., Wayland, B.B., Determination of Organo−Cobalt bond dissociation energetics and thermodynamic properties of organic radicals through equilibrium studies. J. Am. Chem. Soc. 118 (1996), 9102–9109, 10.1021/ja960002c.
[64] Wayland, B.B., Basickes, L., Mukerjee, S., Wei, M., Fryd, M., Living radical polymerization of acrylates initiated and controlled by organocobalt porphyrin complexes. Macromolecules 30 (1997), 8109–8112, 10.1021/ma9707493.
[65] Woska, D.C., Wayland, B.B., Rate constants and activation parameters for organo-cobalt porphyrin bond homolysis from NMR relaxation times. Inorganica Chim. Acta 270 (1998), 197–201, 10.1016/S0020-1693(97)05840-4.
[66] Lu, Z., Fryd, M., Wayland, B.B., New life for living radical polymerization mediated by cobalt(II) metalloradicals. Macromolecules 37 (2004), 2686–2687, 10.1021/ma035924w.
[67] Peng, C.-H., Fryd, M., Wayland, B.B., Organocobalt mediated radical polymerization of acrylic acid in water. Macromolecules 40 (2007), 6814–6819, 10.1021/ma070836n.
[68] Li, S., de Bruin, B., Peng, C.-H., Fryd, M., Wayland, B.B., Exchange of organic radicals with organo-cobalt complexes formed in the living radical polymerization of vinyl acetate. J. Am. Chem. Soc. 130 (2008), 13373–13381, 10.1021/ja804010h.
[69] Peng, C.-H., Scricco, J., Li, S., Fryd, M., Wayland, B.B., Organo-cobalt mediated living radical polymerization of vinyl acetate. Macromolecules 41 (2008), 2368–2373, 10.1021/ma702500b.
[70] de Bruin, B., Dzik, W.I., Li, S., Wayland, B.B., Hydrogen-Atom Transfer in Reactions of Organic Radicals with [Co II (por)]. (por=Porphyrinato) and in Subsequent Addition of [Co(H)(por)] to Olefins. Chem. - A Eur. J. 15 (2009), 4312–4320, 10.1002/chem.200802022.
[71] Peng, C.-H., Li, S., Wayland, B.B., Formation and interconversion of organo-cobalt complexes in reactions of cobalt(II) porphyrins with cyanoalkyl radicals and vinyl olefins. Inorg. Chem. 48 (2009), 5039–5046, 10.1021/ic900384n.
[72] Zhao, Y., Dong, H., Li, Y., Fu, X., Living radical polymerization of acrylates and acrylamides mediated by a versatile cobalt porphyrin complex. Chem. Commun., 48, 2012, 3506, 10.1039/c2cc00114d.
[73] Zhao, Y., Yu, M., Fu, X., Photo-cleavage of the cobalt–carbon bond: visible light-induced living radical polymerization mediated by organo-cobalt porphyrins. Chem. Commun., 49, 2013, 5186, 10.1039/c3cc41466c.
[75] Zhao, Y., Yu, M., Zhang, S., Liu, Y., Fu, X., Visible light induced living/controlled radical polymerization of acrylates catalyzed by cobalt porphyrins. Macromolecules 47 (2014), 6238–6245, 10.1021/ma5014385.
[76] Langlotz, B.K., Lloret Fillol, J., Gross, J.H., Wadepohl, H., Gade, L.H., Living radical polymerization of acrylates mediated by 1,3-Bis(2-pyridylimino)isoindolatocobalt(II) complexes: monitoring the chain growth at the metal. Chem. - A Eur. J. 14 (2008), 10267–10279, 10.1002/chem.200801373.
[77] Li, S.K.K.S.,Y., Gnanou, Y., Baisch, U., Champouret, Y., Poli, R., Robson, K.C.D., McNeil, W.S., Electronic and steric ligand effects in the radical polymerization of vinyl acetate mediated by β-ketoiminate complexes of cobalt(II). Chem. - An Asian J 4 (2009), 1257–1265, 10.1002/asia.200900084.
[78] Nakano, T., Tamada, D., Miyazaki, J., Kakiuchi, K., Okamoto, Y., Asymmetric radical polymerization of maleimides using a chiral cobalt(II) complex. Macromolecules 33 (2000), 1489–1491, 10.1021/ma991544s.
[79] Nakano, T., Yade, T., Okamoto, Y., Revised interpretation for N -cyclohexylmaleimide polymerization in the presence of an optically active cobalt(II) complex: polymerization mediated by anionic species formed through monomer−Co(II) Complex−O 2 interaction. Macromolecules 36 (2003), 3498–3504, 10.1021/ma025857q.
[80] Sherwood, R.K., Kent, C.L., Patrick, B.O., McNeil, W.S., Controlled radical polymerisation of methyl acrylate initiated by a well-defined cobalt alkyl complex. Chem. Commun., 46, 2010, 2456, 10.1039/b922030e.
[81] Liao, C.-M., Hsu, C.-C., Wang, F.-S., Wayland, B.B., Peng, C.-H., Living radical polymerization of vinyl acetate and methyl acrylate mediated by Co(Salen*) complexes. Polym. Chem., 4, 2013, 3098, 10.1039/c3py00282a.
[83] Kumar, K.S.S., Gnanou, Y., Champouret, Y., Daran, J.-C., Poli, R., Radical polymerization of vinyl acetate with bis(tetramethylheptadionato)cobalt(II): coexistence of three different mechanisms. Chem. - A Eur. J. 15 (2009), 4874–4885, 10.1002/chem.200802388.
[84] Detrembleur, C., Versace, D.-L., Piette, Y., Hurtgen, M., Jerome, C., Lalevee, J., Debuigne, A., Synthetic and mechanistic inputs of photochemistry into the bis-acetylacetonatocobalt-mediated radical polymerization of n-butyl acrylate and vinyl acetate. Polym. Chem. 3 (2012), 1856–1866, 10.1039/c1py00443c.
[85] Hurtgen, M., Debuigne, A., Jerome, C., Detrembleur, C., Solving the problem of bis(acetylacetonato)cobalt(II)-mediated radical polymerization (CMRP) of acrylic esters. Macromolecules 43 (2010), 886–894, 10.1021/ma902310c.
[86] Debuigne, A., Warnant, J., Jerome, R., Voets, I., de Keizer, A., Cohen Stuart, M.A., Detrembleur, C., Synthesis of novel well-defined poly(vinyl acetate)-b-poly(acrylonitrile) and derivatized water-soluble poly(vinyl alcohol)-b-poly(acrylic acid) block copolymers by cobalt-mediated radical polymerization. Macromolecules 41 (2008), 2353–2360, 10.1021/ma702341v.
[87] Debuigne, A., Michaux, C., Jerome, C., Jerome, R., Poli, R., Detrembleur, C., Cobalt-mediated radical polymerization of acrylonitrile: kinetics investigations and DFT calculations. Chem. - Eur. J. 14 (2008), 7623–7637, 10.1002/chem.200800371.
[88] Gridnev, A.A., The 25th anniversary of catalytic chain transfer. J. Polym. Sci. Part A Polym. Chem. 38 (2000), 1753–1766.
[89] Gridnev, A.A., Ittel, S.D., Catalytic chain transfer in free-radical polymerizations. Chem. Rev. 101 (2001), 3611–3660, 10.1021/cr9901236.
[90] Li, Y., Wayland, B.B., Macromonomer living character in the cobalt(ii) porphyrin chain transfer catalysis for radical polymerization of methacrylic acid in water. Chem. Commun., 2003, 1594, 10.1039/b302452k.
[91] Li, Y., Wayland, B.B., Macromonomer chain growth in the radical polymerization of MMA by cobalt(II) catalyzed chain transfer. Macromol. Rapid Commun. 24 (2003), 307–310, 10.1002/marc.200390049.
[92] Hurtgen, M., Debuigne, A., Mouithys-Mickalad, A., Jérôme, R., Jérôme, C., Detrembleur, C., Synthesis of poly(vinyl alcohol)/C60 and poly(N- vinylpyrrolidone)/C60 nanohybrids as potential photodynamic cancer therapy agents. Chem. - An Asian J 5 (2010), 859–868.
[93] Morin, A.N., Detrembleur, C., Jerome, C., De Tullio, P., Poli, R., Debuigne, A., Effect of Head-to-Head Addition in Vinyl Acetate Controlled Radical Polymerization: why Is Co(acac)2-Mediated Polymerization so Much Better?. Macromolecules 46 (2013), 4303–4312, 10.1021/ma400651a.
[94] Debuigne, A., Hurtgen, M., Detrembleur, C., Jérôme, C., Barner-Kowollik, C., Junkers, T., Interpolymer radical coupling: a toolbox complementary to controlled radical polymerization. Prog. Polym. Sci. 37 (2012), 1004–1030, 10.1016/j.progpolymsci.2012.01.003.
[95] Debuigne, A., Hurtgen, M., Jerome, C., Detrembleur, C., Radical coupling of polymers formed by cobalt-mediated radical polymerization. ACS Symp. Ser. 1100 (2012), 217–230, 10.1021/bk-2012-1100.ch014.
[96] Debuigne, A., Jerome, C., Detrembleur, C., Isoprene-assisted Radical Coupling of (Co)polymers Prepared by Cobalt- Mediated Radical Polymerization. Angew. Chem., Int. Ed. 48 (2009), 1422–1424, 10.1002/anie.200804880.
[97] Debuigne, A., Poli, R., De Winter, J., Laurent, P., Gerbaux, P., Wathelet, J.-P., Jerome, C., Detrembleur, C., Effective cobalt-mediated radical coupling (CMRC) of poly(vinyl acetate) and poly(N-vinylpyrrolidone) (Co)polymer precursors. Macromolecules 43 (2010), 2801–2813, 10.1021/ma902610m.
[98] Debuigne, A., Poli, R., De Winter, J., Laurent, P., Gerbaux, P., Dubois, P., Wathelet, J.-P., Jerome, C., Detrembleur, C., Cobalt-mediated radical coupling (CMRC): an unusual route to midchain-functionalized symmetrical macromolecules. Chem. - Eur. J. 16 (2010), 1799–1811, 10.1002/chem.200902618.
[99] Iovu, M.C., Matyjaszewski, K., Controlled/living radical polymerization of vinyl acetate by degenerative transfer with alkyl iodides. Macromolecules 36 (2003), 9346–9354, 10.1021/ma034892+.
[100] Kwak, Y., Goto, A., Fukuda, T., Kobayashi, Y., Yamago, S., A systematic study on activation processes in organotellurium-mediated living radical polymerizations of styrene, methyl methacrylate, methyl acrylate, and vinyl acetate. Macromolecules 39 (2006), 4671–4679, 10.1021/ma060295m.
[101] Kermagoret, A., Jerome, C., Detrembleur, C., Debuigne, A., In situ bidentate to tetradentate ligand exchange reaction in cobalt-mediated radical polymerization. Eur. Polym. J. 62 (2015), 312–321, 10.1016/j.eurpolymj.2014.08.003.
[102] Kermagoret, A., Nakamura, Y., Bourguignon, M., Detrembleur, C., Jerome, C., Yamago, S., Debuigne, A., Expanding the scope of controlled radical polymerization via cobalt-tellurium radical exchange reaction. ACS Macro Lett. 3 (2014), 114–118, 10.1021/mz400635h.
[103] Jeon, H.J., Youk, J.H., Synthesis of poly(vinyl acetate)- b -polystyrene and poly(vinyl alcohol)- b -polystyrene copolymers by a combination of cobalt-mediated radical polymerization and RAFT polymerization. Macromolecules 43 (2010), 2184–2189, 10.1021/ma902434z.
[104] Jeon, H.J., Yu, Y.C., Youk, J.H., Synthesis of poly(vinyl acetate)-b-poly(4-vinylpyridine) block copolymers by a combination of cobalt-mediated radical polymerization and RAFT polymerization and their use in dispersion polymerization under UV radiation. Colloid Polym. Sci. 290 (2012), 569–574, 10.1007/s00396-012-2592-3.
[105] Chen, Y.-J., Wu, B.-J., Wang, F.-S., Chi, M.-H., Chen, J.-T., Peng, C.-H., Hybridization of CMRP and ATRP: a direct living chain extension from poly(vinyl acetate) to poly(methyl methacrylate) and polystyrene. Macromolecules 48 (2015), 6832–6838, 10.1021/acs.macromol.5b01101.
[106] Detrembleur, C., Debuigne, A., Jerome, C., Phan, T.N.T., Bertin, D., Gigmes, D., Joining efforts of nitroxide-mediated polymerization (NMP) and cobalt-mediated radical polymerization (CMRP) for the preparation of novel ABC triblock copolymers. Macromolecules 42 (2009), 8604–8607, 10.1021/ma901839v.
[107] Debuigne, A., Caille, J.R., Jérôme, R., Synthesis of end-functional poly(vinyl acetate) by cobalt-mediated radical polymerization. Macromolecules 38 (2005), 5452–5458.
[108] Demarteau, J., Kermagoret, A., German, I., Cordella, D., Robeyns, K., De Winter, J., Gerbaux, P., Jérôme, C., Debuigne, A., Detrembleur, C., Halomethyl-cobalt(bis-acetylacetonate) for the controlled synthesis of functional polymers. Chem. Commun., 2015, 14334–14337, 10.1039/C5CC04714E.
[109] Rostovtsev, V.V., Green, L.G., Fokin, V.V., Sharpless, K.B., A Stepwise Huisgen Cycloaddition Process: Copper(I)-catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes. Angew. Chemie Int. Ed. 41 (2002), 2596–2599, 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2–4.
[110] Iha, R.K., Wooley, K.L., Nyström, A.M., Burke, D.J., Kade, M.J., Hawker, C.J., Applications of orthogonal “click” chemistries in the synthesis of functional soft materials. Chem. Rev. 109 (2009), 5620–5686, 10.1021/cr900138t.
[111] Yamago, S., Nakamura, Y., Recent progress in the use of photoirradiation in living radical polymerization. Polymer 54 (2013), 981–994 http://dx.doi.org/10.1016/j.polymer.2012.11.046.
[112] Dadashi-Silab, S., Doran, S., Yagci, Y., Photoinduced electron transfer reactions for macromolecular syntheses. Chem. Rev. 116 (2016), 10212–10275, 10.1021/acs.chemrev.5b00586.
[113] Kräutler, B., Acetyl-cobalamin from photoinduced carbonylation of methyl-cobalamin. Helv. Chim. Acta 67 (1984), 1053–1059, 10.1002/hlca.19840670418.
[114] Ghosez, B.G.A., Goebel, T., Syntheses and reactions of glycosyl- cobaloximes. Chem. Ber. 121 (1988), 1807–1811.
[115] Branchaud, B.P., Meier, M.S., Choi, Y., Alkyl-alkenyl cross coupling via alkyl cobaloxime radical chemistry.An alkyl equivalent to the heck reaction compatible with common organic functional groups. Tetrahedron Lett. 29 (1988), 167–170, 10.1016/S0040-4039(00)80043-X.
[116] Coveney, D.J., Patel, V.F., Pattenden, G., Acylcobalt salophen reagents. Precursors to acyl radical intermediates for inter- and intra-molecular oxidative michael addition reactions. Tetrahedron Lett. 28 (1987), 5949–5952, 10.1016/S0040-4039(01)81098-4.
[119] Ding, D., Pan, X., Zhang, Z., Li, N., Zhu, J., Zhu, X., A degradable copolymer of 2-methylene-1,3-dioxepane and vinyl acetate by photo-induced cobalt-mediated radical polymerization. Polym. Chem. 7 (2016), 5258–5264, 10.1039/C6PY01061J.
[120] Kermagoret, A., Wenn, B., Debuigne, A., Jérôme, C., Junkers, T., Detrembleur, C., Improved photo-induced cobalt-mediated radical polymerization in continuous flow photoreactors. Polym. Chem. 6 (2015), 3847–3857, 10.1039/C5PY00299K.
[121] Tonhauser, C., Natalello, A., Löwe, H., Frey, H., Microflow technology in polymer synthesis. Macromolecules 45 (2012), 9551–9570, 10.1021/ma301671x.
[122] Hornung, C.H., Guerrero-Sanchez, C., Brasholz, M., Saubern, S., Chiefari, J., Moad, G., Rizzardo, E., Thang, S.H., Controlled RAFT polymerization in a continuous flow microreactor. Org. Process Res. Dev. 15 (2011), 593–601, 10.1021/op1003314.
[123] Boyere, C., Jerome, C., Debuigne, A., Input of supercritical carbon dioxide to polymer synthesis: an overview. Eur. Polym. J. 61 (2014), 45–63, 10.1016/j.eurpolymj.2014.07.019.
[124] Thurecht, K.J., Howdle, S.M., Controlled dispersion polymerization in supercritical carbon dioxide. Aust. J. Chem. 62 (2009), 786–789 http://dx.doi.org/10.1071/CH09081.
[125] Zetterlund, P.B., Aldabbagh, F., Okubo, M., Controlled/living heterogeneous radical polymerization in supercritical carbon dioxide. J. Polym. Sci. Part A Polym. Chem. 47 (2009), 3711–3728, 10.1002/pola.23432.
[126] Birkin, N.A., Arrowsmith, N.J., Park, E.J., Richez, A.P., Howdle, S.M., Synthesis and application of new CO2-soluble vinyl pivalate hydrocarbon stabilisers via RAFT polymerisation. Polym. Chem. 2 (2011), 1293–1299, 10.1039/C1PY00062D.
[127] Kermagoret, A., Chau, N.D.Q., Grignard, B., Cordella, D., Debuigne, A., Jérôme, C., Detrembleur, C., Cobalt-mediated radical polymerization of vinyl acetate and acrylonitrile in supercritical carbon dioxide. Macromol. Rapid Commun. 37 (2016), 539–544, 10.1002/marc.201500629.
[128] Bunck, D.N., Sorenson, G.P., Mahanthappa, M.K., Cobalt-mediated radical polymerization routes to poly(vinyl ester) block copolymers. J. Polym. Sci. Part A Polym. Chem. 49 (2011), 242–249, 10.1002/pola.24445.
[129] Nzé, R.-P., Colombani, O., Nicol, E., Synthesis of poly(vinyl laurate)-b-poly(vinyl stearate) diblock copolymers by cobalt-mediated radical polymerization in solution. J. Polym. Sci. Part A Polym. Chem. 50 (2012), 4046–4054, 10.1002/pola.26205.
[130] Bryaskova, R., Detrembleur, C., Debuigne, A., Jerome, R., Cobalt-mediated radical polymerization (CMRP) of vinyl acetate initiated by redox systems: toward the scale-up of CMRP. Macromolecules 39 (2006), 8263–8268, 10.1021/ma060339r.
[131] Allaoua, I., Goi, B.E., Obadia, M.M., Debuigne, A., Detrembleur, C., Drockenmuller, E., (Co)Polymerization of vinyl levulinate by cobalt-mediated radical polymerization and functionalization by ketoxime click chemistry. Polym. Chem. 5 (2014), 2973–2979, 10.1039/c3py01505j.
[132] Obadia, M.M., Colliat-Dangus, G., Debuigne, A., Serghei, A., Detrembleur, C., Drockenmuller, E., Poly(vinyl ester 1,2,3-triazolium)s: a new member of the poly(ionic liquid)s family. Chem. Commun. 51 (2015), 3332–3335, 10.1039/C4CC08847F.
[133] Busch, M., Roth, M., Stenzel, M.H., Davis, T.P., Barner-Kowollik, C., The use of novel F-RAFT agents in high temperature and high pressure ethene polymerization: can control be achieved?. Aust. J. Chem. 60 (2007), 788–793 http://dx.doi.org/10.1071/CH07200.
[134] Dommanget, C., D'Agosto, F., Monteil, V., Polymerization of Ethylene through Reversible Addition-fragmentation Chain Transfer (RAFT). Angew. Chemie Int. Ed 53 (2014), 6683–6686, 10.1002/anie.201403491.
[135] Nakamura, A., Ito, S., Nozaki, K., Coordination−Insertion copolymerization of fundamental polar monomers. Chem. Rev. 109 (2009), 5215–5244, 10.1021/cr900079r.
[136] Boffa, L.S., Novak, B.M., Copolymerization of polar monomers with olefins using transition-metal complexes. Chem. Rev. 100 (2000), 1479–1494, 10.1021/cr990251u.
[137] Ito, S., Munakata, K., Nakamura, A., Nozaki, K., Copolymerization of vinyl acetate with ethylene by palladium/Alkylphosphine−Sulfonate catalysts. J. Am. Chem. Soc. 131 (2009), 14606–14607, 10.1021/ja9050839.
[138] Leicht, H., Göttker-Schnetmann, I., Mecking, S., Incorporation of Vinyl Chloride in Insertion Polymerization. Angew. Chemie Int. Ed. 52 (2013), 3963–3966, 10.1002/anie.201209724.
[139] Gu, B., Liu, S., Leber, J.D., Sen, A., Nitroxide-mediated copolymerization of methyl acrylate with 1-alkenes and Norbornenes. Macromolecules 37 (2004), 5142–5144, 10.1021/ma049395n.
[140] Venkatesh, R., Harrisson, S., Haddleton, D.M., Klumperman, B., Olefin copolymerization via controlled radical polymerization: copolymerization of acrylate and 1-octene. Macromolecules 37 (2004), 4406–4416, 10.1021/ma035986m.
[141] Tanaka, K., Matyjaszewski, K., Controlled copolymerization of n -butyl acrylate with Nonpolar 1-alkenes using activators regenerated by electron transfer for atom-transfer radical polymerization. Macromolecules 40 (2007), 5255–5260, 10.1021/ma070822h.
[142] Venkatesh, R., Staal, B.B.P., Klumperman, B., Olefin copolymerization via reversible addition–fragmentation chain transfer. Chem. Commun., 2004, 1554–1555, 10.1039/B403342F.
[143] Mishima, E., Tamura, T., Yamago, S., Controlled copolymerization of 1-octene and (Meth)acrylates via organotellurium-mediated living radical polymerization (TERP). Macromolecules 45 (2012), 8998–9003, 10.1021/ma301570r.
[144] Borkar, S., Sen, A., Controlled copolymerization of vinyl acetate with 1-alkenes and their fluoro derivatives by degenerative transfer. J. Polym. Sci. Part A Polym. Chem. 43 (2005), 3728–3736, 10.1002/pola.20802.
[145] Kermagoret, A., Debuigne, A., Jérôme, C., Detrembleur, C., Precision design of ethylene- and polar-monomer-based copolymers by organometallic-mediated radical polymerization. Nat. Chem. 6 (2014), 179–187 http://www.ncbi.nlm.nih.gov/pubmed/24557131.
[146] J. Demarteau, A. Kermagoret, C. Jérôme, C. Detrembleur, A. Debuigne, Controlled synthesis of ethylene-vinyl acetate based copolymers by organometallic mediated radical polymerization, in: ACS Symp. Ser., Control. Radic. Polym. vol. 1188, 2015: pp. 47–61. http://dx.doi.org/10.1021/bk-2015-1188.ch004.
[147] Bryaskova, R., Willet, N., Degée, P., Dubois, P., Jérôme, R., Detrembleur, C., Copolymerization of vinyl acetate with 1-octene and ethylene by cobalt-mediated radical polymerization. J. Polym. Sci. Part A Polym. Chem. 45 (2007), 2532–2542, 10.1002/pola.21963.
[148] Braun, D., Controlled free-radical polymerization of vinyl chloride. J. Vinyl Addit. Technol. 11 (2005), 86–90, 10.1002/vnl.20043.
[149] Starnes, W.H., Structural defects in poly(vinyl chloride). J. Polym. Sci. Part A Polym. Chem. 43 (2005), 2451–2467, 10.1002/pola.20811.
[150] Starnes, W.H., Ge, X., Mechanism of autocatalysis in the thermal dehydrochlorination of poly(vinyl chloride). Macromolecules 37 (2004), 352–359, 10.1021/ma0352835.
[151] Starnes, W.H., Structural and mechanistic aspects of the thermal degradation of poly(vinyl chloride). Prog. Polym. Sci. 27 (2002), 2133–2170, 10.1016/S0079-6700(02)00063-1.
[152] Wannemacher, T., Braun, D., Pfaendner, R., Novel copolymers via nitroxide mediated controlled free radical polymerization of vinyl chloride. Macromol. Symp. 202 (2003), 11–24, 10.1002/masy.200351202.
[155] Sienkowska, M.J., Rosen, B.M., Percec, V., SET-LRP of vinyl chloride initiated with CHBr 3 in DMSO at 25 °C. J. Polym. Sci. Part A Polym. Chem. 47 (2009), 4130–4140, 10.1002/pola.23536.
[156] Hatano, T., Rosen, B.M., Percec, V., SET-LRP of vinyl chloride initiated with CHBr 3 and catalyzed by Cu(0)-wire/TREN in DMSO at 25 °C. J. Polym. Sci. Part A Polym. Chem. 48 (2010), 164–172, 10.1002/pola.23774.
[157] Percec, V., Guliashvili, T., Ladislaw, J.S., Wistrand, A., Stjerndahl, A., Sienkowska, M.J., Monteiro, M.J., Sahoo, S., Ultrafast synthesis of ultrahigh molar mass polymers by metal-catalyzed living radical polymerization of acrylates, methacrylates, and vinyl chloride mediated by SET at 25 °C. J. Am. Chem. Soc. 128 (2006), 14156–14165, 10.1021/ja065484z.
[158] Coelho, J.F.J., Fonseca, A.C., Gonçalves, P.M.O.F., Popov, A.V., Gil, M.H., Scaling-up of poly(vinyl chloride) prepared by single electron transfer–degenerative chain transfer mediated living radical polymerization in water media—II: high molecular weight-ultra stable PVC. Chem. Eng. Sci. 69 (2012), 122–128, 10.1016/j.ces.2011.10.008.
[159] Percec, V., Popov, A.V., Ramirez-Castillo, E., Coelho, J.F.J., Hinojosa-Falcon, L.A., Non-transition metal-catalyzed living radical polymerization of vinyl chloride initiated with iodoform in water at 25 °C. J. Polym. Sci. Part A Polym. Chem. 42 (2004), 6267–6282, 10.1002/pola.20481.
[160] Percec, V., Popov, A.V., Ramirez-Castillo, E., Monteiro, M., Barboiu, B., Weichold, O., Asandei, A.D., Mitchell, C.M., Aqueous room temperature metal-catalyzed living radical polymerization of vinyl chloride. J. Am. Chem. Soc. 124 (2002), 4940–4941, 10.1021/ja0256055.
[161] Percec, V., Popov, A.V., Ramirez-Castillo, E., Single-electron-transfer/degenerative-chain-transfer mediated living radical polymerization of vinyl chloride catalyzed by thiourea dioxide/octyl viologen in water/tetrahydrofuran at 25°C. J. Polym. Sci. Part A Polym. Chem. 43 (2005), 287–295, 10.1002/pola.20496.
[162] Percec, V., Popov, A.V., Ramirez-Castillo, E., Coelho, J.F.J., Single electron transfer-degenerative chain transfer mediated living radical polymerization (SET-DTLRP) of vinyl chloride initiated with methylene iodide and catalyzed by sodium dithionite. J. Polym. Sci. Part A Polym. Chem. 43 (2005), 773–778, 10.1002/pola.20543.
[163] Percec, V., Sienkowska, M.J., Synthesis of the four-arm star-block copolymer [PVC- b -PBA-CH(CH3)-CO-O-CH2]4C by SET-DTLRP initiated from a tetrafunctional initiator. J. Polym. Sci. Part A Polym. Chem. 47 (2009), 628–634, 10.1002/pola.23188.
[164] Percec, V., Guliashvili, T., Popov, A.V., Ramirez-Castillo, E., Coelho, J.F.J., Hinojosa-Falcon, L.A., Accelerated synthesis of poly(methyl methacrylate)-b-poly(vinyl chloride)-b-poly(methyl methacrylate) block copolymers by the CuCl/tris(2-dimethylaminoethyl)amine-catalyzed living radical block copolymerization of methyl methacrylate initiated with α,ω-di. J. Polym. Sci. Part A Polym. Chem. 43 (2005), 1649–1659, 10.1002/pola.20616.
[165] Maximiano, P., Mendes, J.P., Mendonça, P.V., Abreu, C.M.R., Guliashvili, T., Serra, A.C., Coelho, J.F.J., Cyclopentyl methyl ether: a new green co-solvent for supplemental activator and reducing agent atom transfer radical polymerization. J. Polym. Sci. Part A Polym. Chem. 53 (2015), 2722–2729, 10.1002/pola.27736.
[166] Mendes, J.P., Branco, F., Abreu, C.M.R., Mendonça, P.V., Serra, A.C., Popov, A.V., Guliashvili, T., Coelho, J.F.J., Sulfolane: an efficient and universal solvent for copper-mediated atom transfer radical (co)Polymerization of acrylates, methacrylates, styrene, and vinyl chloride. ACS Macro Lett. 3 (2014), 858–861, 10.1021/mz5003883.
[167] Piette, Y., Debuigne, A., Jerome, C., Bodart, V., Poli, R., Detrembleur, C., Cobalt-mediated radical (co)polymerization of vinyl chloride and vinyl acetate. Polym. Chem. 3 (2012), 2880–2891, 10.1039/c2py20413d.
[169] Nakabayashi, K., Mori, H., Recent progress in controlled radical polymerization of N-vinyl monomers. Eur. Polym. J. 49 (2013), 2808–2838, 10.1016/j.eurpolymj.2013.07.006.
[170] Moad, G., Rizzardo, E., Thang, S.H., Living radical polymerization by the RAFT process. Aust. J. Chem., 58, 2005, 379, 10.1071/CH05072.
[171] Pound, G., McLeary, J.B., McKenzie, J.M., Lange, R.F.M., Klumperman, B., In-situ NMR spectroscopy for probing the efficiency of RAFT/MADIX agents. Macromolecules 39 (2006), 7796–7797, 10.1021/ma061843z.
[172] Guinaudeau, A., Mazières, S., Wilson, D.J., Destarac, M., Aqueous RAFT/MADIX polymerisation of N-vinyl pyrrolidone at ambient temperature. Polym. Chem. 3 (2012), 81–84, 10.1039/C1PY00373A.
[173] Devasia, R., Bindu, R.L., Borsali, R., Mougin, N., Gnanou, Y., Controlled radical polymerization of N-Vinylpyrrolidone by reversible addition-fragmentation chain transfer process. Macromol. Symp. 229 (2005), 8–17, 10.1002/masy.200551102.
[174] Wan, D., Zhou, Q., Pu, H., Yang, G., Controlled radical polymerization ofN-vinylcaprolactam mediated by xanthate or dithiocarbamate. J. Polym. Sci. Part A Polym. Chem. 46 (2008), 3756–3765, 10.1002/pola.22722.
[175] Beija, M., Marty, J.-D., Destarac, M., Thermoresponsive poly(N-vinyl caprolactam)-coated gold nanoparticles: sharp reversible response and easy tunability. Chem. Commun., 47, 2011, 2826, 10.1039/c0cc05184e.
[176] Lu, X., Gong, S., Meng, L., Li, C., Yang, S., Zhang, L., Controllable synthesis of poly(N-vinylpyrrolidone) and its block copolymers by atom transfer radical polymerization. Polymer 48 (2007), 2835–2842, 10.1016/j.polymer.2007.03.048.
[177] Singh, P., Srivastava, A., Kumar, R., Synthesis of amphiphilic poly(N-vinylcaprolactam) using ATRP protocol and antibacterial study of its silver nanocomposite. J. Polym. Sci. Part A Polym. Chem. 50 (2012), 1503–1514, 10.1002/pola.25911.
[178] Yusa, S., Yamago, S., Sugahara, M., Morikawa, S., Yamamoto, T., Morishima, Y., Thermo-responsive diblock copolymers of poly( N -isopropylacrylamide) and poly( N -vinyl-2-pyrroridone) synthesized via organotellurium-mediated controlled radical polymerization (TERP). Macromolecules 40 (2007), 5907–5915, 10.1021/ma070769x.
[179] Shi, L., Chapman, T.M., Beckman, E.J., Poly(ethylene glycol)- block -poly( N -vinylformamide) copolymers synthesized by the RAFT methodology. Macromolecules 36 (2003), 2563–2567, 10.1021/ma025670z.
[180] Debuigne, A., Morin, A.N., Kermagoret, A., Piette, Y., Detrembleur, C., Jerome, C., Poli, R., Key role of intramolecular metal chelation and hydrogen bonding in the cobalt-mediated radical polymerization of N-Vinyl amides. Chem. - Eur. J. 18 (2012), 12834–12844, 10.1002/chem.201201456.
[181] Debuigne, A., Schoumacher, M., Willet, N., Riva, R., Zhu, X., Ruetten, S., Jerome, C., Detrembleur, C., New functional poly(N-vinylpyrrolidone) based (co)polymers via photoinitiated cobalt-mediated radical polymerization. Chem. Commun. 47 (2011), 12703–12705, 10.1039/c1cc15471k.
[182] Dréan, M., Guégan, P., Detrembleur, C., Jérôme, C., Rieger, J., Debuigne, A., Controlled synthesis of poly(vinylamine)-based copolymers by organometallic-mediated radical polymerization. Macromolecules 49 (2016), 4817–4827, 10.1021/acs.macromol.6b00992.
[183] Debuigne, A., Willet, N., Jerome, R., Detrembleur, C., Amphiphilic poly(vinyl acetate)-b-poly(N-vinylpyrrolidone) and novel double hydrophilic poly(vinyl alcohol)-b-poly(N-vinylpyrrolidone) block copolymers prepared by cobalt-mediated radical polymerization. Macromolecules 40 (2007), 7111–7118, 10.1021/ma0712908.
[184] Mumtaz, M., Labrugère, C., Cloutet, E., Cramail, H., Synthesis of Poly(3,4-ethylenedioxythiophene) latexes using poly(N-vinylpyrrolidone)-based copolymers as reactive stabilizers. J. Polym. Sci. Part A Polym. Chem. 48 (2010), 3841–3855, 10.1002/pola.24171.
[185] Jeon, H.J., You, Y.C., Youk, J.H., Synthesis and characterization of amphiphilic poly( N -vinyl pyrrolidone)- b -poly(ε-caprolactone) copolymers by a combination of cobalt-mediated radical polymerization and ring-opening polymerization. J. Polym. Sci. Part A Polym. Chem. 47 (2009), 3078–3085, 10.1002/pola.23396.
[186] Jeon, H.J., You, Y., Yoon, M.J., Youk, J.H., Preparation of polyacrylonitrile nanoparticles via dispersion polymerization of acrylonitrile using a poly(N-vinyl pyrrolidone)-cobalt complex in an aqueous system. Polymer 52 (2011), 3905–3911, 10.1016/j.polymer.2011.07.022.
[187] Vihola, H., Laukkanen, A., Valtola, L., Tenhu, H., Hirvonen, J., Cytotoxicity of thermosensitive polymers poly(N-isopropylacrylamide), poly(N-vinylcaprolactam) and amphiphilically modified poly(N-vinylcaprolactam). Biomaterials 26 (2005), 3055–3064, 10.1016/j.biomaterials.2004.09.008.
[188] Meeussen, F., Phase behaviour of poly(N-vinyl caprolactam) in water. Polymer 41 (2000), 8597–8602, 10.1016/S0032-3861(00)00255-X.
[189] Roy, D., Brooks, W.L.A., Sumerlin, B.S., New directions in thermoresponsive polymers. Chem. Soc. Rev., 42, 2013, 7214, 10.1039/c3cs35499g.
[190] Liu, J., Debuigne, A., Detrembleur, C., Jerome, C., Poly(N-vinylcaprolactam): a thermoresponsive macromolecule with promising future in biomedical field. Adv. Healthc. Mater 3 (2014), 1941–1968, 10.1002/adhm.201400371.
[191] Hurtgen, M., Liu, J., Debuigne, A., Jerome, C., Detrembleur, C., Synthesis of thermo-responsive poly(N-vinylcaprolactam)-containing block copolymers by cobalt-mediated radical polymerization. J. Polym. Sci. Part A Polym. Chem. 50 (2012), 400–408, 10.1002/pola.25045.
[192] Liu, J., Detrembleur, C., Hurtgen, M., Debuigne, A., De Pauw-Gillet, M.-C., Mornet, S., Duguet, E., Jerome, C., Reversibly crosslinked thermo- and redox-responsive nanogels for controlled drug release. Polym. Chem. 5 (2014), 77–88, 10.1039/c3py00839h.
[193] Liu, J., Detrembleur, C., Debuigne, A., De Pauw-Gillet, M.-C., Mornet, S., Vander Elst, L., Laurent, S., Duguet, E., Jerome, C., Glucose-, pH- and thermo-responsive nanogels crosslinked by functional superparamagnetic maghemite nanoparticles as innovative drug delivery systems. J. Mat. Chem. B 2 (2014), 1009–1023, 10.1039/c3tb21272f.
[194] Liu, J., Detrembleur, C., Hurtgen, M., Debuigne, A., De Pauw-Gillet, M.-C., Mornet, S., Duguet, E., Jerome, C., Thermo-responsive gold/poly(vinyl alcohol)-b-poly(N-vinylcaprolactam) core-corona nanoparticles as a drug delivery system. Polym. Chem. 5 (2014), 5289–5299, 10.1039/C4PY00352G.
[195] Kermagoret, A., Fustin, C.-A., Bourguignon, M., Detrembleur, C., Jerome, C., Debuigne, A., One-pot controlled synthesis of double thermoresponsive N-vinylcaprolactam-based copolymers with tunable LCSTs. Polym. Chem. 4 (2013), 2575–2583, 10.1039/c3py00134b.
[196] Kermagoret, A., Mathieu, K., Thomassin, J.-M., Fustin, C.-A., Duchene, R., Jerome, C., Detrembleur, C., Debuigne, A., Double thermoresponsive di- and triblock copolymers based on N-vinylcaprolactam and N-vinylpyrrolidone: synthesis and comparative study of solution behaviour. Polym. Chem. 5 (2014), 6534–6544, 10.1039/C4PY00852A.
[197] Thomassin, J.-M., Mathieu, K., Kermagoret, A., Fustin, C.-A., Jerome, C., Debuigne, A., Double thermo-responsive hydrogels from poly(vinylcaprolactam) containing diblock and triblock copolymers. Polym. Chem., 2015, 1856–1864, 10.1039/C4PY01606H.
[198] Gu, L., Zhu, S., Hrymak, A.N., Acidic and basic hydrolysis of poly(N-vinylformamide). J. Appl. Polym. Sci. 86 (2002), 3412–3419, 10.1002/app.11364.
[199] Witek, E., Pazdro, M., Bortel, E., Mechanism for base hydrolysis of poly(N-vinylformamide). J. Macromol. Sci. Part A 44 (2007), 503–507, 10.1080/10601320701235461.
[200] Zhu, J., Gosen, C., Marchant, R.E., Synthesis and characterization of poly(vinyl amine)-based amphiphilic comb-like dextran glycopolymers by a two-step method. J. Polym. Sci. Part A Polym. Chem. 44 (2006), 192–199, 10.1002/pola.20998.
[201] Akashi, M., Nakano, S., Kishida, A., Synthesis of poly(N-vinylisobutyramide) from poly(N-vinylacetamide) and its thermosensitive property. J. Polym. Sci. Part A Polym. Chem. 34 (1996), 301–303, 10.1002/(SICI)1099-0518(19960130)34:2<301::AID-POLA16>3.0.CO;2-U.
[202] Akashi, M., Saihata, S., Yashima, E., Sugita, S., Marumo, K., Novel nonionic and cationic hydrogels prepared from N-vinylacetamide. J. Polym. Sci. Part A Polym. Chem. 31 (1993), 1153–1160, 10.1002/pola.1993.080310509.
[203] Pinschmidt, R.K., Polyvinylamine at last. J. Polym. Sci. Part A Polym. Chem. 48 (2010), 2257–2283, 10.1002/pola.23992.
[204] Kobayashi, S., Do Suh, K., Shirokura, Y., Chelating ability of poly(vinylamine): effects of polyamine structure on chelation. Macromolecules 22 (1989), 2363–2366, 10.1021/ma00195a062.
[205] Toutianoush, A., El-Hashani, A., Schnepf, J., Tieke, B., Multilayer membranes of p-sulfonato-calix[8]arene and polyvinylamine and their use for selective enrichment of rare earth metal ions. Appl. Surf. Sci. 246 (2005), 430–436, 10.1016/j.apsusc.2004.11.048.
[206] Pelton, R., Polyvinylamine: a tool for engineering interfaces. Langmuir, 30, 2014, 10.1021/la5017214.
[207] Geffroy, C., Labeau, M., Wong, K., Cabane, B., Cohen Stuart, M., Kinetics of adsorption of polyvinylamine onto cellulose, colloids surfaces a physicochem. Eng. Asp. 172 (2000), 47–56, 10.1016/S0927-7757(00)00499-4.
[209] Katchalsky, A., Mazur, J., Spitnik, P., SECTION II: polybase properties of polyvinylamine. J. Polym. Sci. 23 (1957), 513–532, 10.1002/pol.1957.1202310401.
[210] Maki, Y., Mori, H., Endo, T., Controlled RAFT polymerization of N-vinylphthalimide and its hydrazinolysis to poly(vinyl amine). Macromol. Chem. Phys. 208 (2007), 2589–2599, 10.1002/macp.200700330.
[211] Dréan, M., Debuigne, A., Jéröme, C., Goncalves, C., Midoux, P., Rieger, J., Guégan, P., Use of primary and secondary polyvinylamines for efficient gene transfection. Biomacromolecules, 2016 ASAP. http://dx.doi.org/10.1021/acs.biomac.6b01526.
[212] Mecerreyes, D., Polymeric ionic liquids: broadening the properties and applications of polyelectrolytes. Prog. Polym. Sci. 36 (2011), 1629–1648 http://dx.doi.org/10.1016/j.progpolymsci.2011.05.007.
[213] Yuan, J., Mecerreyes, D., Antonietti, M., Poly(ionic liquid)s: an update. Prog. Polym. Sci. 38 (2013), 1009–1036 http://dx.doi.org/10.1016/j.progpolymsci.2013.04.002.
[214] Coupillaud, P., Taton, D., Imidazolium-based poly(ionic liquid) block copolymers. Mecerreyes, D., (eds.) Appl. Ion. Liq. Polym. Sci. Technol, 2015, Springer Berlin Heidelberg, Berlin, Heidelberg, 69–102, 10.1007/978-3-662-44903-5_4.
[215] Shaplov, A.S., Marcilla, R., Mecerreyes, D., Recent advances in innovative polymer electrolytes based on poly(ionic liquid)s. Electrochim. Acta 175 (2015), 18–34 http://dx.doi.org/10.1016/j.electacta.2015.03.038.
[216] Meek, K.M., Elabd, Y.A., Polymerized ionic liquid block copolymers for electrochemical energy. J. Mat. Chem. A 3 (2015), 24187–24194, 10.1039/C5TA07170D.
[217] Mori, H., Yahagi, M., Endo, T., RAFT polymerization of N-Vinylimidazolium salts and synthesis of thermoresponsive ionic liquid block copolymers. Macromolecules 42 (2009), 8082–8092, 10.1021/ma901180j.
[218] Yuan, J., Schlaad, H., Giordano, C., Antonietti, M., Double hydrophilic diblock copolymers containing a poly(ionic liquid) segment: controlled synthesis, solution property, and application as carbon precursor. Eur. Polym. J. 47 (2011), 772–781 http://dx.doi.org/10.1016/j.eurpolymj.2010.09.030.
[219] Detrembleur, C., Debuigne, A., Hurtgen, M., Jerome, C., Pinaud, J., Fevre, M., Coupillaud, P., Vignolle, J., Taton, D., Synthesis of 1-Vinyl-3-ethylimidazolium-Based ionic liquid (Co)polymers by cobalt-mediated radical polymerization. Macromolecules 44 (2011), 6397–6404, 10.1021/ma201041s.
[220] Coupillaud, P., Fevre, M., Wirotius, A.-L., Aissou, K., Fleury, G., Debuigne, A., Detrembleur, C., Mecerreyes, D., Vignolle, J., Taton, D., Precision synthesis of poly(ionic liquid)-based block copolymers by cobalt-mediated radical polymerization and preliminary study of their self-assembling properties. Macromol. Rapid Commun. 35 (2014), 422–430, 10.1002/marc.201300776.
[221] Cordella, D., Kermagoret, A., Debuigne, A., Riva, R., German, I., Isik, M., Jerome, C., Mecerreyes, D., Taton, D., Detrembleur, C., Direct route to well-defined poly(ionic liquid)s by controlled radical polymerization in water. ACS Macro Lett. 3 (2014), 1276–1280, 10.1021/mz500721r.
[222] Weiss-Maurin, M., Cordella, D., Jérôme, C., Taton, D., Detrembleur, C., Direct one-pot synthesis of poly(ionic liquid) nanogels by cobalt-mediated radical cross-linking copolymerization in organic or aqueous media. Polym. Chem. 7 (2016), 2521–2530, 10.1039/C6PY00112B.
[223] Cordella, D., Kermagoret, A., Debuigne, A., Jérôme, C., Mecerreyes, D., Isik, M., Taton, D., Detrembleur, C., All poly(ionic liquid)-based block copolymers by sequential controlled radical copolymerization of vinylimidazolium monomers. Macromolecules 48 (2015), 5230–5243, 10.1021/acs.macromol.5b01013.
[224] Canning, S.L., Smith, G.N., Armes, S.P., A critical appraisal of RAFT-mediated polymerization-induced self-assembly. Macromolecules 49 (2016), 1985–2001, 10.1021/acs.macromol.5b02602.
[225] Charleux, B., Delaittre, G., Rieger, J., D'Agosto, F., Polymerization-induced self-assembly: from soluble macromolecules to block copolymer nano-objects in one step. Macromolecules 45 (2012), 6753–6765, 10.1021/ma300713f.
[226] Cordella, D., Debuigne, A., Jérôme, C., Kochovski, Z., Taton, D., Detrembleur, C., One-pot synthesis of double poly(ionic liquid) block copolymers by cobalt-mediated radical polymerization-induced self-assembly (CMR-PISA) in water. Macromol. Rapid Commun. 37 (2016), 1181–1187, 10.1002/marc.201600039.
[227] Mokbel, H., Poriel, C., Rault-Berthelot, J., Dumur, F., Gigmes, D., Toufaily, J., Hamieh, T., Cordella, D., Detrembleur, C., Fouassier, J.P., Lalevée, J., A glance at violet LED sensitive photoinitiators based on the spiroxanthene scaffold. J. Appl. Polym. Sci. 133 (2016), 43213–43221, 10.1002/app.43213.
[228] Mäkiniemi, R.O., Das, P., Hönders, D., Grygiel, K., Cordella, D., Detrembleur, C., Yuan, J., Walther, A., Conducting, self-assembled, nacre-mimetic polymer/clay nanocomposites. ACS Appl. Mat. Interfaces 7 (2015), 15681–15685, 10.1021/acsami.5b04676.
[229] Mäkiniemi, R.O., Das, P., Hönders, D., Grygiel, K., Cordella, D., Detrembleur, C., Yuan, J., Walther, A., Conducting, self-assembled, nacre-mimetic polymer/clay nanocomposites. ACS Appl. Mat. Interfaces 7 (2015), 15681–15685, 10.1021/acsami.5b04676.
[230] Patil, N., Cordella, D., Aqil, A., Debuigne, A., Admassie, S., Jérôme, C., Detrembleur, C., Surface- and redox-active multifunctional polyphenol-derived poly(ionic liquid)s: controlled synthesis and characterization. Macromolecules 49 (2016), 7676–7691, 10.1021/acs.macromol.6b01857.