Interpolymer radical coupling: A toolbox complementary to controlled radical polymerization

[en] The current review focuses on the relevance and practical benefit of interpolymer radical coupling methods. The latter are developing rapidly and constitute a perfectly complementary macromolecular engineering toolbox to the controlled radical polymerization techniques (CRP). Indeed, all structures formed by CRP are likely to be prone to radical coupling reactions, which multiply the available synthetic possibilities. Basically, the coupling systems can be divided in two main categories. The first one, including the atom transfer radical coupling (ATRC), silane radical atom abstraction (SRAA) and cobalt-mediated radical coupling (CMRC), relies on the recombination of macroradicals produced from a dormant species. The second one, including atom transfer nitroxide radical coupling (ATNRC), single electron transfer nitroxide radical coupling (SETNRC), enhanced spin capturing polymerization (ESCP) and nitrone/nitroso mediated radical coupling (NMRC), makes use of a radical scavenger in order to promote the conjugation of the polymer chains. More than a compilation of macromolecular engineering achievements, the present review additionally aims to emphasize the particularities, synthetic potential and present limitations of each system.

Research center :

Center for Education and Research on Macromolecules (CERM)

Disciplines :

Materials science & engineering
Chemistry

Author, co-author :

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

Hurtgen, Marie ; 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)

Jérôme, Christine ; Université de Liège - ULiège > Department of Chemistry > Center for Education and Research on Macromolecules (CERM)

Barner-Kowollik, Christopher; Karlsruhe Institute of Technology (KIT), Germany > Institut für Technische Chemie und Polymerchemie > Preparative Macromolecular Chemistry

Junkers, Thomas; University of Hasselt, Belgium > Institute for Materials Research (IMO) > Polymer Reaction Design Group

Language :

English

Title :

Interpolymer radical coupling: A toolbox complementary to controlled radical polymerization

Publication date :

July 2012

Journal title :

Progress in Polymer Science

ISSN :

0079-6700

Publisher :

Elsevier Science

Volume :

Issue :

Pages :

1004-1030

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://pdn.sciencedirect.com/science?_ob=MiamiImageURL&_cid=271613&_user=532038&_pii=S0079670012000160&_check=y&_origin=browse&_zone=rslt_list_item&_coverDate=2012-07-31&wchp=dGLbVlS-zSkzV&md5=2370bb3f84ff329fd62d5653ef99f99c&pid=1-s2.0-S0079670012000160-main.pdf

Funders :

BELSPO - SPP Politique scientifique - Service Public Fédéral de Programmation Politique scientifique
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE]
FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen [BE]
The Karlsruhe Institute of Technology

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since 29 May 2012

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Bibliography

M.K. Georges, R.P.N. Veregin, P.M. Kazmaier, and G.K. Hamer Narrow molecular weight resins by a free-radical polymerization process Macromolecules 26 1993 2987 2988
C.J. Hawker, A.W. Bosman, and E. Harth New polymer synthesis by nitroxide mediated living radical polymerizations Chem Rev 101 2001 3661 3688
V. Sciannamea, R. Jerome, and C. Detrembleur In situ nitroxide-mediated radical polymerization (NMP) processes: their understanding and optimization Chem Rev 108 2008 1104 1126
W.A. Braunecker, and K. Matyjaszewski Controlled/living radical polymerization: features, developments, and perspectives Prog Polym Sci 32 2007 93 146
M. Ouchi, T. Terashima, and M. Sawamoto Transition metal-catalyzed living radical polymerization: toward perfection in catalysis and precision polymer synthesis Chem Rev 109 2009 4963 5050
F. di Lena, and K. Matyjaszewski Transition metal catalysts for controlled radical polymerization Prog Polym Sci 35 2010 959 1021
G. Moad, E. Rizzardo, and S.H. Thang Toward living radical polymerization Acc Chem Res 41 2008 1133 1142
C. Barner-Kowollik Handbook of RAFT polymerization 2008 Wiley VCH Weinheim
G. David, C. Boyer, J. Tonnar, B. Ameduri, P. Lacroix-Desmazes, and B. Boutevin Use of iodocompounds in radical polymerization Chem Rev 106 2006 3936 3962
S. Yamago Precision polymer synthesis by degenerative transfer controlled/living radical polymerization using organotellurium, organostibine, and organobismuthine chain-transfer agents Chem Rev 109 2009 5051 5068
R. Poli Relationship between one-electron transition-metal reactivity and radical polymerization processes Angew Chem Int Ed 45 2006 5058 5070
K.M. Smith, W.S. McNeil, and A.S. Abd-El-Aziz Organometallic-mediated radical polymerization: developing well-defined complexes for reversible transition metal-alkyl bond homolysis Macromol Chem Phys 211 2010 10 16
M. Hurtgen, C. Detrembleur, C. Jerome, and A. Debuigne Insight into organometallic mediated radical polymerization Polym Rev 51 2011 188 213
A. Debuigne, R. Poli, C. Jerome, R. Jerome, and C. Detrembleur Overview of cobalt-mediated radical polymerization: roots, state of the art and future prospects Prog Polym Sci 34 2009 211 239
H. Fischer Unusual selectivities of radical reactions by internal suppression of fast modes J Am Chem Soc 108 1986 3925 3927
K. Matyjaszewski, S. Coca, S.G. Gaynor, M. Wei, and B.B. Woodworth Zerovalent metals in controlled/"living" radical polymerization Macromolecules 30 1997 7348 7350
C. Yoshikawa, A. Goto, and T. Fukuda Reactions of polystyrene radicals in a monomer-free atom transfer radical polymerization system e-Polymers 013 2002 1 12
G. Odian Principles of polymerization 4th ed. 2004 Wiley-Interscience New York
T. Sarbu, K.-Y. Lin, J. Ell, D.J. Siegwart, J. Spanswick, and K. Matyjaszewski Polystyrene with designed molecular weight distribution by atom transfer radical coupling Macromolecules 37 2004 3120 3127
W. Tang, and K. Matyjaszewski Effect of ligand structure on activation rate constants in ATRP Macromolecules 39 2006 4953 4959
M. Bednarek, T. Biedron, and P. Kubisa Studies of atom transfer radical polymerization (ATRP) of acrylates by MALDI TOF mass spectrometry Macromol Chem Phys 201 2000 58 66
S.G. Roos, and A.H.E. Muller Evidence for chain transfer in the atom transfer radical polymerization of butyl acrylate Macromol Rapid Commun 21 2000 864 867
K.M. Domingues, and E.S. Tillman Radical-radical coupling of polystyrene chains using AGET ATRC J Polym Sci Part A: Polym Chem 48 2010 5737 5745
W. Jakubowski, and K. Matyjaszewski Activator generated by electron transfer for atom transfer radical polymerization Macromolecules 38 2005 4139 4146
W. Jakubowski, K. Min, and K. Matyjaszewski Activators regenerated by electron transfer for atom transfer radical polymerization of styrene Macromolecules 39 2006 39 45
B. Otazaghine, G. David, B. Boutevin, J.J. Robin, and K. Matyjaszewski Synthesis of telechelic oligomers via atom transfer radical polymerization, 1 study of styrene Macromol Chem Phys 205 2004 154 164
S. Faucher, P. Okrutny, and S. Zhu Facile and effective purification of polymers produced by atom transfer radical polymerization via simple catalyst precipitation and microfiltration Macromolecules 39 2006 3 5
B. Nottelet, P. Lacroix-Desmazes, and B. Boutevin Atom transfer radical coupling of polystyrene and poly(methyl acrylate) synthesized by reverse iodine transfer polymerization Polymer 48 2007 50 57
B. Otazaghine, C. Boyer, J.-J. Robin, and B. Boutevin Synthesis of telechelic oligomers by atom transfer radical polymerization: a study of acrylate monomers J Polym Sci Part A: Polym Chem 43 2005 2377 2394
B. Otazaghine, and B. Boutevin Synthesis of telechelic oligomers via atom transfer radical polymerization. 3. Study of butyl α-fluoroacrylate Macromol Chem Phys 205 2004 2002 2011
T. Sarbu, K.-Y. Lin, J. Spanswick, R.R. Gil, D.J. Siegwart, and K. Matyjaszewski Synthesis of hydroxy-telechelic poly(methyl acrylate) and polystyrene by atom transfer radical coupling Macromolecules 37 2004 9694 9700
C.-F. Huang, Y. Ohta, A. Yokoyama, and T. Yokozawa Efficient low-temperature atom transfer radical coupling and its application to synthesis of well-defined symmetrical polybenzamides Macromolecules 44 2011 4140 4148
K. Matyjaszewski, T.E. Patten, and J. Xia Controlled/"living" radical polymerization.kinetics of the homogeneous atom transfer radical polymerization of styrene J Am Chem Soc 119 1997 674 680
K.A. Davis, Paik H-j, and K. Matyjaszewski Kinetic investigation of the atom transfer radical polymerization of methyl acrylate Macromolecules 32 1999 1767 1776
F. Heatley, P.A. Lovell, and T. Yamashita Chain transfer to polymer in free-radical solution polymerization of 2-ethylhexyl acrylate studied by NMR spectroscopy Macromolecules 34 2001 7636 7641
T. Junkers, and C. Barner-Kowollik The role of mid-chain radicals in acrylate free radical polymerization: branching and scission J Polym Sci Part A: Polym Chem 46 2008 7585 7605
C. Plessis, G. Arzamendi, J.M. Alberdi, M. Agnely, J.R. Leiza, and J.M. Asua Intramolecular chain transfer to polymer in the emulsion polymerization of 2-ethylhexyl acrylate Macromolecules 34 2001 6138 6143
J.M. Asua, S. Beuermann, M.B. Buback, P. Castignolles, B. Charleux, R.G. Gilbert, R.A. Hutchinson, J.R. Leiza, A.N. Nikitin, J.-P. Vairon, and A.M. van Herk Critically evaluated rate coefficients for free-radical polymerization, 5 propagation rate coefficient for butyl acrylate Macromol Chem Phys 205 2004 2151 2160
J. March Advanced organic chemistry: reactions, mechanisms, and structure 1992 Wiley Interscience New York
K. Matyjaszewski, H.-J. Paik, P. Zhou, and S. Diamanti Determination of activation and deactivation rate constants of model compounds in atom transfer radical polymerization Macromolecules 34 2001 5125 5131
D. Shipp, J.-L. Wang, and K. Matyjaszewski Synthesis of acrylate and methacrylate block copolymers using atom transfer radical polymerization Macromolecules 31 1998 8005 8008
K. Matyjaszewski, D. Shipp, G. McMurtry, S. Gaynor, and T. Pakula Simple and effective one-pot synthesis of (meth)acrylic block copolymers through atom transfer radical polymerization J Polym Sci Part A: Polym Chem 38 2000 2023 2031
S. Yurteri, I. Cianga, and Y. Yagci Synthesis and characterization of alpha, w-telechelic polymers by atom transfer radical polymerization and coupling processes Macromol Chem Phys 204 2003 1771 1783
B. Aydogan, and Y. Yagci Studies on the preparation of alpha, w-telechelic polymers by the combination of reverse atom transfer radical polymerization and atom transfer radical coupling processes Turk J Chem 31 2007 1 10
E.J. Goethals Telechelic polymers: synthesis and applications 1989 CRC Press Boca Raton, FL
B. Boutevin, G. David, and C. Boyer Telechelic oligomers and macromonomers by radical techniques Adv Polym Sci 206 2007 31 135
M.A. Tasdelen, M.U. Kahveci, and Y. Yagci Telechelic polymers by living and controlled/living polymerization methods Prog Polym Sci 36 2011 455 567
V. Coessens, T. Pintauer, and K. Matyjaszewski Functional polymers by atom transfer radical polymerization Prog Polym Sci 26 2001 337 377
Y.Y. Durmaz, I. Cianga, and Y. Yagci Studies on the preparation of telechelic polymers by atom transfer radical polymerization and cross coupling processes e-Polymers 050 2006 1 9
H. Gao, D.J. Siegwart, N. Jahed, T. Sarbu, and K. Matyjaszewski Characterization of α,ω-dihydroxypolystyrene by gradient polymer elution chromatography and two-dimensional liquid chromatography Des Monomers Polym 8 2005 533 546
Y. Qin, C. Cui, and F. Jaekle Silylated Initiators for the efficient preparation of borane-end-functionalized polymers via ATRP Macromolecules 40 2007 1413 1420
J. Xia, and K. Matyjaszewski Controlled/"living" radical polymerization. Homogeneous reverse atom transfer radical polymerization using AIBN as the initiator Macromolecules 30 1997 7692 7696
J.T. Kopping, Z.P. Tolstyka, and H.D. Maynard Telechelic aminooxy polystyrene synthesized by ATRP and ATR coupling Macromolecules 40 2007 8593 8599
A. Postma, T.P. Davis, G. Moad, and M.S. O'Shea Approaches to phthalimido and amino end-functional polystyrene by atom transfer radical polymerization (ATRP) React Funct Polym 66 2006 137 147
Z.P. Tolstyka, J.T. Kopping, and H.D. Maynard Straightforward synthesis of cysteine-reactive telechelic polystyrene Macromolecules 41 2008 599 606
Z. Zhang, Q. Fu, and J. Huang A simple way for synthesis of alkyne-telechelic poly(methyl methacrylate) via single electron transfer radical coupling reaction Chin J Chem 28 2010 1327 1330
M.H. Wrue, A.C. McUmber, and M. Anthamatten Atom transfer radical polymerization of end-functionalized hydrogen-bonding polymers and resulting polymer miscibility Macromolecules 42 2009 9255 9262
G. Toquer, S. Monge, K. Antonova, C. Blanc, M. Nobili, and J.-J. Robin Synthesis via ATRP and anchoring properties of ammonium-terminated monofunctional or telechelic polystyrenes Macromol Chem Phys 208 2007 94 102
R. Nagelsdiek, H. Keul, and H. Hoecker A new approach to multiblock copolymers using atom transfer radical coupling e-Polymers 049 2005 1 11
X. Luo, G. Wang, and J. Huang Preparation of H-shaped ABCAB terpolymers by atom transfer radical coupling J Polym Sci Part A: Polym Chem 47 2009 59 68
R. Sugi, A. Yokoyama, T. Furuyama, M. Uchiyama, and T. Yokozawa Inductive effect-assisted chain-growth polycondensation. synthetic development from para- to meta-substituted aromatic polyamides with low polydispersities J Am Chem Soc 127 2005 10172 10173
A.F. Voter, and E.S. Tillman Synthesis of macrocyclic polystyrene using intramolecular atom transfer radical coupling Polym Prepr (Am Chem Soc Div Polym Chem) 51 2 2010 536 537
A.F. Voter, and E.S. Tillman An easy and efficient route to macrocyclic polymers via intramolecular radical-radical coupling of chain ends Macromolecules 43 2010 10304 10310
D. Sasaki, Y. Suzuki, T. Hagiwara, S. Yano, and T. Sawaguchi Synthesis and applications of triblock and multiblock copolymers using telechelic oligopropylene Polymer 49 2008 4094 4100
X. Jiang, M. Vamvakaki, and R. Narain Copper-catalyzed bimolecular coupling of α,ω-dibromide-functionalized poly(γ-caprolactone) Macromolecules 43 2010 3228 3232
I. Cianga, and Y. Yagci First polyrecombination reaction via atom transfer radical coupling (ATRC), a new way for the synthesis of poly(p-xylylene) Des Monomers Polym 10 2007 575 584
Y.Y. Durmaz, B. Aydogan, I. Cianga, and Y. Yagci The use of atom transfer radical coupling reactions for the synthesis of various macromolecular structures ACS Symp Ser 1023 2009 171 187
X. Jiang, Y. Chen, and F. Xi Stepwise cleavable star polymers and polymeric gels thereof Macromolecules 43 2010 7056 7061
C. Chatgilialoglu Structural and chemical properties of silyl radicals Chem Rev 95 1995 1229 1251
C. Chatgilialoglu, and V.I. Timokhin Silyl radicals in chemical synthesis Adv Organomet Chem 57 2008 117 181
R. Braslau, A. Tsimelzon, and J. Gewandter Novel methodology for the synthesis of N-alkoxyamines Org Lett 6 2004 2233 2235
S. Thakur, and E.S. Tillman Efficient metal-free coupling of polystyrene chains using silane radical atom abstraction J Polym Sci Part A: Polym Chem 45 2007 3488 3493
J. Lalevee, A. Dirani, M. El-Roz, X. Allonas, and J.P. Fouassier Silanes as new highly efficient co-initiators for radical polymerization in aerated media Macromolecules 41 2008 2003 2010
S. Thakur, J.R. Smith, E.S. Tillman, N.A. Cohen, and N.D. Contrella 9-Bromoanthracene photodimers as initiators in controlled radical polymerization: silane radical atom abstraction coupled with nitroxide mediated polymerization J Polym Sci Part A: Polym Chem 46 2008 6016 6022
J. Lalevee, N. Blanchard, M. El-Roz, B. Graff, X. Allonas, and J.P. Fouassier New photoinitiators based on the silyl radical chemistry: polymerization ability, ESR spin trapping, and laser flash photolysis investigation Macromolecules 41 2008 4180 4186
S. Thakur, N.A. Cohen, and E.S. Tillman Chain extension and block copolymer synthesis using silane radical atom abstraction coupled with nitroxide mediated polymerization Polymer 49 2008 1483 1489
H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angew Chem Int Ed 40 2001 2004 2021
C. Barner-Kowollik, P.F.E. Du, P. Espeel, C.J. Hawker, T. Junkers, H. Schlaad, and C.W. Van "Clicking" polymers or just efficient linking: what is the difference? Angew Chem Int Ed 50 2011 60 62
K. Matyjaszewski, B.E. Woodworth, X. Zhang, S.G. Gaynor, and Z. Metzner Simple and efficient synthesis of various alkoxyamines for stable free radical polymerization Macromolecules 31 1998 5955 5957
Q. Fu, W. Lin, and J. Huang A new strategy for preparation of graft copolymers via "graft onto" by atom transfer nitroxide radical coupling chemistry: preparation of poly(4-glycidyloxy-2,2,6,6- tetramethylpiperidine-1-oxyl-co-ethylene oxide)-graft-polystyrene and poly(tert-butyl acrylate) Macromolecules 41 2008 2381 2387
V. Percec, T. Guliashvili, J.S. Ladislaw, A. Wistrand, A. Stjerndahl, M.J. Sienkowska, M.J. Monteiro, and S. Sahoo 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
B.M. Rosen, and V. Percec Single-electron transfer and single-electron transfer degenerative chain transfer living radical polymerization Chem Rev 109 2009 5069 5119
Q. Fu, Z. Zhang, W. Lin, and J. Huang Single-electron-transfer nitroxide-radical-coupling reaction at ambient temperature: application in the synthesis of block copolymers Macromolecules 42 2009 4381 4383
W. Lin, R. Jing, G. Wang, and J. Huang Synthesis of amphiphilic ABC triblock copolymers by single electron transfer nitroxide radical coupling reaction in tetrahydrofuran J Polym Sci Part A: Polym Chem 49 2011 2802 2810
J. Kulis, C.A. Bell, A.S. Micallef, Z. Jia, and M.J. Monteiro Rapid, selective, and reversible nitroxide radical coupling (NRC) reactions at ambient temperature Macromolecules 42 2009 8218 8227
J. Kulis, C.A. Bell, A.S. Micallef, and M.J. Monteiro Kinetic analysis of nitroxide radical coupling reactions mediated by CuBr J Polym Sci Part A: Polym Chem 48 2010 2214 2223
Z. Jia, C.A. Bell, and M.J. Monteiro Rapid and highly efficient functionalization of polymer bromide end-groups by SET-NRC Macromolecules 44 2011 1747 1751
W. Lin, B. Huang, Q. Fu, G. Wang, and J. Huang Investigation of nitroxide radical coupling reaction in wide temperature range and different catalyst system J Polym Sci Part A: Polym Chem 48 2010 2991 2999
W. Lin, Q. Fu, Y. Zhang, and J. Huang One-pot synthesis of ABC type triblock copolymers via a combination of "click chemistry" and atom transfer nitroxide radical coupling chemistry Macromolecules 41 2008 4127 4135
R. Jing, W. Lin, G. Wang, and J. Huang Copper(0)-catalyzed one-pot synthesis of ABC triblock copolymers via the combination of single electron transfer nitroxide radical coupling reaction and "click" chemistry J Polym Sci Part A: Polym Chem 49 2011 2594 2600
H. Durmaz, G. Hizal, and U. Tunca Linear tetrablock quaterpolymers via triple click reactions, azide-alkyne, diels-alder, and nitroxide radical coupling in a one-pot fashion J Polym Sci Part A: Polym Chem 49 2011 1962 1968
A.J. Inglis, and C. Barner-Kowollik Ultra rapid approaches to mild macromolecular conjugation Macromol Rapid Commun 31 2010 1247 1266
Q. Fu, G. Wang, W. Lin, and J. Huang One-pot preparation of 3-miktoarm star terpolymers via "click chemistry" and atom transfer nitroxide radical coupling reaction J Polym Sci Part A: Polym Chem 47 2009 986 990
C. Liu, M. Pan, Y. Zhang, and J. Huang Preparation of star block copolymers with polystyrene-block-poly(ethylene oxide) as side chains on hyperbranched polyglycerol core by combination of ATRP with atom transfer nitroxide radical coupling reaction J Polym Sci Part A: Polym Chem 46 2008 6754 6761
Y. Li, Y. Zhang, D. Yang, J. Hu, G. Lu, and X. Huang Star-like PAA-g-PPO well-defined amphiphilic graft copolymer synthesized by ATNRC and SET-NRC reaction J Polym Sci Part A: Polym Chem 48 2010 2084 2097
Y. Li, Y. Zhang, S. Zhai, Y. Deng, H. Xiong, G. Lu, and X. Huang Synthesis of starlike PtBA-g-PEO amphiphilic graft copolymer via highly efficient Cu-catalyzed SET-NRC reaction at ambient temperature J Polym Sci Part A: Polym Chem 49 2011 23 34
Y. Li, Y. Zhang, D. Yang, Y. Li, J. Hu, C. Feng, S. Zhai, G. Lu, and X. Huang PAA-g-PPO amphiphilic graft copolymer: synthesis and diverse micellar morphologies Macromolecules 43 2010 262 270
Q. Fu, C. Liu, W. Lin, and J. Huang One-pot synthesis of heterograft copolymers via "graft onto" by atom transfer nitroxide radical coupling chemistry J Polym Sci Part A: Polym Chem 46 2008 6770 6779
R. Jing, G. Wang, and J. Huang One-pot preparation of ABA-type block-graft copolymers via a combination of "click" chemistry with atom transfer nitroxide radical coupling reaction J Polym Sci Part A: Polym Chem 48 2010 5430 5438
N. Cerit, N. Cakir, A. Dag, O. Sirkecioglu, H. Durmaz, G. Hizal, and U. Tunca Various brush polymers through ring opening metathesis polymerization and nitroxide radical coupling reaction J Polym Sci Part A: Polym Chem 49 2011 2850 2858
G. Wang, Y. Zhang, and J. Huang Effects of Br connected groups on atom transfer nitroxide radical coupling reaction and its application in the synthesis of comb-like block copolymers J Polym Sci Part A: Polym Chem 48 2010 1633 1640
R. Sun, G. Wang, C. Liu, and J. Huang Preparation of comb-like copolymers with amphiphilic poly(ethylene oxide)-b-polystyrene graft chains by combination of "graft from" and "graft onto" strategies J Polym Sci Part A: Polym Chem 47 2009 1930 1938
X. Fan, G. Wang, and J. Huang Synthesis of macrocyclic molecular brushes with amphiphilic block copolymers as side chains J Polym Sci Part A: Polym Chem 49 2011 1361 1367
R. Nicolay, and K. Matyjaszewski Synthesis of cyclic (Co)polymers by atom transfer radical cross-coupling and ring expansion by nitroxide-mediated polymerization Macromolecules 44 2011 240 247
J. Kulis, C.A. Bell, A.S. Micallef, and M.J. Monteiro Ultrafast and reversible multiblock formation by the set-nitroxide radical coupling reaction Aust J Chem 63 2010 1227 1236
R. Nicolay, L. Marx, P. Hemery, and K. Matyjaszewski Synthesis of multisegmented degradable polymers by atom transfer radical cross-coupling Macromolecules 40 2007 9217 9223
C.A. Bell, Z.-F. Jia, J. Kulis, and M.J. Monteiro Modulating two copper(I)-catalyzed orthogonal "click" reactions for the one-pot synthesis of highly branched polymer architectures at 25 °C Macromolecules 44 2011 4814 4827
Z. Jia, C.A. Bell, and M.J. Monteiro Directing the pathway of orthogonal click' reactions by modulating copper-catalytic activity Chem Commun 47 2011 4165 4167
K. Sui, C. Yang, S. Gao, X. Shan, Y. Xia, and Q. Zheng A novel route for well-defined polystyrene-grafted multiwalled carbon nanotubes via the radical coupling reaction J Appl Polym Sci 114 2009 1914 1920
Y. Deng, Y. Li, J. Dai, M. Lang, and X. Huang An efficient way to functionalize graphene sheets with presynthesized polymer via ATNRC chemistry J Polym Sci Part A: Polym Chem 49 2011 1582 1590
T.J. Kemp Kinetic aspects of spin trapping Prog React Kinet Mech 24 1999 287 358
E.G. Janzen, P.H. Krygsman, D.A. Lindsay, and D.L. Haire Detection of alkyl, alkoxyl, and alkyperoxyl radicals from the thermolysis of azobis(isobutyronitrile) by ESR/spin trapping. Evidence for double spin adducts from liquid-phase chromatography and mass spectroscopy J Am Chem Soc 112 1990 8279 8284
E. Finkelstein, G.M. Rosen, and E.J. Rauckman Spin trapping. Kinetics of the reaction of superoxide and hydroxyl radicals with nitrones J Am Chem Soc 102 1980 4994 4999
E.G. Janzen, Y.Y. Wang, and R.V. Shetty Spin trapping with α-pyridyl 1-oxide N-tert-butyl nitrones in aqueous solutions. A unique electron spin resonance spectrum for the hydroxyl radical adduct J Am Chem Soc 100 1978 2923 2925
E.G. Janzen Spin trapping Acc Chem Res 4 1971 31 40
K.V. Gothelf, and K.A. Jorgensen Asymmetric 1,3-dipolar cycloaddition reactions Chem Rev 98 1998 863 909
J. Hamer, and A. Macaluso Nitrones Chem Rev 64 1964 473 495
D.S.C. Black, R.F. Crozier, and V.C. Davis 1,3-Dipolar cycloaddition reactions of nitrones Synth. Stuttgart 1975 205 221
E.H.H. Wong, T. Junkers, and C. Barner-Kowollik Enhanced spin capturing polymerization: an efficient and versatile protocol for controlling molecular weight distributions J Polym Sci Part A: Polym Chem 46 2008 7273 7279
E.H.H. Wong, M.H. Stenzel, T. Junkers, and C. Barner-Kowollik The kinetics of enhanced spin capturing polymerization: influence of the nitrone structure J Polym Sci Part A: Polym Chem 47 2009 1098 1107
T. Junkers, E.H.H. Wong, M.H. Stenzel, and C. Barner-Kowollik Formation efficiency of ABA block copolymers via enhanced spin capturing polymerization (ESCP): locating the alkoxyamine function Macromolecules 42 2009 5027 5035
E.H.H. Wong, M.H. Stenzel, T. Junkers, and C. Barner-Kowollik Spin capturing with "clickable" nitrones: generation of miktoarmed star polymers Macromolecules 43 2010 3785 3793
L. Zang, E.H.H. Wong, C. Barner-Kowollik, and T. Junkers Control of methyl methacrylate radical polymerization via enhanced spin capturing polymerization (ESCP) Polymer 51 2010 3821 3825
T. Junkers, L. Zang, E.H.H. Wong, and C. Barner-Kowollik Formation of triblock copolymers via a tandem enhanced spin capturing - nitroxide-mediated polymerization reaction sequence J Polym Sci Polym Chem 49 2011 4841 4850
E.H.H. Wong, C. Boyer, M.H. Stenzel, C. Barner-Kowollik, and T. Junkers Spin capturing with nitrones: radical coupling reactions with concurrent introduction of mid-chain functionality Chem Commun 46 2010 1959 1961
E.H.H. Wong, M.H. Stenzel, T. Junkers, and C. Barner-Kowollik Embedding multiple site-specific functionalities into polymer chains via nitrone-mediated radical coupling reactions J Polym Sci Part A: Polym Chem 49 2011 2118 2126
C. Detrembleur, A. Debuigne, O. Altintas, M. Conradi, E.H.H. Wong, C. Jérôme, C. Barner-Kowollik, and T. Junkers Synthesis of star and H-shape polymers via a combination of cobalt-mediated radical polymerization and nitrone-mediated radical coupling reactions Polym Chem 3 2012 135 147
E.H.H. Wong, O. Altintas, M.H. Stenzel, C. Barner-Kowollik, and T. Junkers Nitrone-mediated radical coupling reactions: a new synthetic tool exemplified on dendrimer synthesis Chem Commun 47 2011 5491 5493
C. Zhang, and Q. Wang Degradable multisegmented polymers synthesized by consecutive radical addition-coupling reaction of α,ω- macrobiradicals and nitroso compound J Polym Sci Part A: Polym Chem 49 2011 612 618
E. Rosa, A. Guerrero, M.P. Bosch, and L. Julia EPR/spin-trapping study of free radical intermediates in the photolysis of trifluoromethyl ketones with initiators Magn Reson Chem 48 2010 198 204
K. Huvaere, and L.H. Skibsted Light-induced oxidation of tryptophan and histidine. Reactivity of aromatic N-heterocycles toward triplet-excited flavins J Am Chem Soc 131 2009 8049 8060
C. Zhang, J. Ling, and Q. Wang Radical addition-coupling polymerization (RACP) toward periodic copolymers Macromolecules 44 2011 8739 8743
Z. Zhang, G. Wang, and J. Huang Synthesis of H-shaped A3BA3 copolymer by methyl-2-nitrosopropane induced single electron transfer nitroxide radical coupling J Polym Sci Part A: Polym Chem 49 2011 2811 2817
B.B. Wayland, G. Poszmik, S.L. Mukerjee, and M. Fryd Living radical polymerization of acrylates by organocobalt porphyrin complexes J Am Chem Soc 116 1994 7943 7944
R.K. Sherwood, C.L. Kent, B.O. Patrick, and W.S. McNeil Controlled radical polymerisation of methyl acrylate initiated by a well-defined cobalt alkyl complex Chem Commun 46 2010 2456 2458
B.K. Langlotz, J.L. Fillol, J.H. Gross, H. Wadepohl, and L.H. Gade Living radical polymerization of acrylates mediated by 1,3-bis(2-pyridylimino) isoindolatocobalt(II) complexes: monitoring the chain growth at the metal Chem Eur J 14 2008 10267 10279
B.B. Wayland, C.-H. Peng, X. Fu, Z. Lu, and M. Fryd Degenerative transfer and reversible termination mechanisms for living radical polymerizations mediated by cobalt porphyrins Macromolecules 39 2006 8219 8222
A. Debuigne, C. Michaux, C. Jerome, R. Jerome, R. Poli, and C. Detrembleur Cobalt-mediated radical polymerization of acrylonitrile: kinetics investigations and DFT calculations Chem Eur J 14 2008 7623 7637
A. Debuigne, J.-R. Caille, and R. Jerome Highly efficient cobalt-mediated radical polymerization of vinyl acetate Angew Chem Int Ed 44 2005 1101 1104
A. Debuigne, Y. Champouret, R. Jerome, R. Poli, and C. Detrembleur 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
C.-H. Peng, J. Scricco, S. Li, M. Fryd, and B.B. Wayland Organo-cobalt mediated living radical polymerization of vinyl acetate Macromolecules 41 2008 2368 2373
S. Maria, H. Kaneyoshi, K. Matyjaszewski, and R. Poli 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 Eur J 13 2007 2480 2492
H. Kaneyoshi, and K. Matyjaszewski Radical (Co)polymerization of vinyl chloroacetate and N-vinylpyrrolidone mediated by bis(acetylacetonate)cobalt derivatives Macromolecules 39 2006 2757 2763
A. Debuigne, N. Willet, R. Jerome, and C. Detrembleur 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
M. Hurtgen, J. Liu, A. Debuigne, C. Jerome, and C. Detrembleur 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
C. Detrembleur, A. Debuigne, M. Hurtgen, C. Jerome, J. Pinaud, M. Fevre, P. Coupillaud, J. Vignolle, and D. Taton Synthesis of 1-Vinyl-3- ethylimidazolium-Based Ionic Liquid (Co)polymers by Cobalt-Mediated Radical Polymerization Macromolecules 44 2011 6397 6404
A. Debuigne, J. Warnant, R. Jerome, I. Voets, A. de Keizer, M.A. Cohen Stuart, and C. Detrembleur 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
A. Debuigne, C. Jerome, and C. Detrembleur Isoprene-assisted radical coupling of (Co)polymers prepared by cobalt-mediated radical polymerization Angew Chem Int Ed 48 2009 1422 1424
A. Debuigne, R. Poli, J. De Winter, P. Laurent, P. Gerbaux, P. Dubois, J.-P. Wathelet, C. Jerome, and C. Detrembleur Cobalt-mediated radical coupling (CMRC): an unusual route to midchain-functionalized symmetrical macromolecules Chem Eur J 16 2010 1799 1811
M. Kamachi, and A. Kajiwara ESR study on radical polymerizations of diene compounds. Determination of propagation rate constants Macromolecules 29 1996 2378 2382
A. Debuigne, R. Poli, J. De Winter, P. Laurent, P. Gerbaux, J.-P. Wathelet, C. Jerome, and C. Detrembleur Effective cobalt-mediated radical coupling (CMRC) of poly(vinyl acetate) and poly(N-vinylpyrrolidone) (Co)polymer precursors Macromolecules 43 2010 2801 2813
A. Debuigne, M. Schoumacher, R. Riva, N. Willet, X. Zhu, S. Ruetten, C. Jérôme, and C. Detrembleur New functional poly(N-vinylpyrrolidone) based (co)polymers via photoinitiated cobalt-mediated radical polymerization Chem Commun 47 2011 12703 12705