Arget atrp of methyl methacrylate in the presence of nitrogen-based ligands as reducing agents
Abstract
BACKGROUND: Activators regenerated by electron transfer for atom transfer radical polymerization (ARGET ATRP) employs reducing agents (e.g. ascorbic acid, tin(II) 2‐ethylhexanoate) to continuously reduce a deactivator Cu(II) to an activator Cu(I) species. In this work, copper‐mediated ARGET ATRP of methyl methacrylate (MMA) was studied in the presence of excess aliphatic nitrogen‐based ligands that served not only as ligands but also as reducing agents. RESULTS: Reduction of Cu(II) to Cu(I) by an excess amount of nitrogen‐based ligand was followed by UV‐visible spectroscopy. Well‐controlled poly(methyl methacrylate) (PMMA) with low polydispersity index (PDI) was prepared in the presence of Cu(II)Br 2/excess ligand via ARGET ATRP. Chain extension of PMMA with MMA was successful, resulting in low‐PDI PMMA and demonstrating well‐maintained end‐group functionality. CONCLUSION: Well‐controlled PMMA with low PDI was prepared via ARGET ATRP in the presence of Cu(II) and nitrogen‐based ligands without any additional reducing agent. Aliphatic nitrogen‐based ligands for ATRP can serve as reducing agents as well as ligands. Copyright © 2009 Society of Chemical Industry
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Miniemulsion ARGET ATRP was developed by the same group and used for the preparation of homopolymers and block copolymers.
“Later on, miniemulsion ARGET ATRP was developed by the same group and used for the preparation of homopolymers and block copolymers [26,27].”
From Block Copolymers: Synthesis, Self-Assembly, and Applications (2017) · cites this paper as [27]
Cites
Atom Transfer Radical Polymerization
Matyjaszewski, K. A., & Xia, J. (2001) · Chemical Reviews · doi:10.1021/cr940534g · Cited by 7,646 · see citing works
Self-citationWang, J.-S., & Matyjaszewski, K. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00125a035 · Cited by 4,622 · see citing works
Self-citationNew Polymer Synthesis by Nitroxide Mediated Living Radical Polymerizations
Hawker, C. J., Bosman, A. W., & Harth, E. M. (2001) · Chemical Reviews · doi:10.1021/cr990119u · Cited by 3,853 · see citing works
Metal-Catalyzed Living Radical Polymerization
Kamigaito, M., Ando, T., & Sawamoto, M. (2001) · Chemical Reviews · doi:10.1021/cr9901182 · Cited by 3,277 · see citing works
Controlled/living radical polymerization: Features, developments, and perspectives
Braunecker, W. A., & Matyjaszewski, K. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.11.002 · Cited by 3,202 · see citing works
Self-citationKato, M., Kamigaito, M., Sawamoto, M., & Higashimura, T. (1995) · Macromolecules · doi:10.1021/ma00109a056 · Cited by 3,046 · see citing works
Narrow molecular weight resins by a free-radical polymerization process
Georges, M. K., Veregin, R. P. N., Kazmaier, P. M., & Hamer, G. K. (1993) · Macromolecules · doi:10.1021/ma00063a054 · Cited by 2,088 · see citing works
Wang, J., & Matyjaszewski, K. (1995) · Macromolecules · doi:10.1021/ma00127a042 · Cited by 1,699 · see citing works
Self-citationLiving Radical Polymerization by the RAFT Process – A Third Update
Moad, G., Rizzardo, E., & Thang, S. H. (2012) · Australian Journal of Chemistry · doi:10.1071/ch12295 · Cited by 1,697 · see citing works
The development of microgels/nanogels for drug delivery applications
Oh, J. K., Drumright, R., Siegwart, D. J., & Matyjaszewski, K. A. (2008) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2008.01.002 · Cited by 1,601 · see citing works
Self-citationHandbook of Radical Polymerization
Matyjaszewski, K. A., & Davis, T. P. (2002) · Wiley eBooks · doi:10.1002/0471220450 · Cited by 1,595 · see citing works
Self-citationLiving ring-opening metathesis polymerization
Bielawski, C. W., & Grubbs, R. H. (2006) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.08.006 · Cited by 1,522 · see citing works
Radical addition–fragmentation chemistry in polymer synthesis
Moad, G., Rizzardo, E., & Thang, S. H. (2008) · Polymer · doi:10.1016/j.polymer.2007.11.020 · Cited by 1,397 · see citing works
Tsarevsky, N. V., & Matyjaszewski, K. A. (2007) · Chemical Reviews · doi:10.1021/cr050947p · Cited by 1,278 · see citing works
Self-citationFunctional polymers by atom transfer radical polymerization
Coessens, V., Pintauer, T., & Matyjaszewski, K. A. (2001) · Progress in Polymer Science · doi:10.1016/s0079-6700(01)00003-x · Cited by 1,256 · see citing works
Self-citationCylindrical molecular brushes: Synthesis, characterization, and properties
Sheiko, S. S., Sumerlin, B. S., & Matyjaszewski, K. A. (2008) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2008.05.001 · Cited by 1,172 · see citing works
Self-citationKinetics of living radical polymerization
Goto, A., & Fukuda, T. (2004) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2004.01.002 · Cited by 914 · see citing works
Diminishing catalyst concentration in atom transfer radical polymerization with reducing agents
Matyjaszewski, K. A., Jakubowski, W., Min, K., Tang, W., Huang, J., Braunecker, W. A., & Tsarevsky, N. V. (2006) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0602675103 · Cited by 883 · see citing works
Self-citationLiving Radical Polymerization by the RAFT Process—A First Update
Moad, G., Rizzardo, E., & Thang, S. H. (2006) · Australian Journal of Chemistry · doi:10.1071/ch06250 · Cited by 847 · see citing works
Activators Regenerated by Electron Transfer for Atom Transfer Radical Polymerization of Styrene
Jakubowski, W., Min, K., & Matyjaszewski, K. A. (2005) · Macromolecules · doi:10.1021/ma0522716 · Cited by 790 · see citing works
Self-citationPintauer, T., & Matyjaszewski, K. A. (2008) · Chemical Society Reviews · doi:10.1039/b714578k · Cited by 745 · see citing works
Self-citationLowe, A. B., & McCormick, C. L. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.11.003 · Cited by 713 · see citing works
Grafting from Surfaces for “Everyone”: ARGET ATRP in the Presence of Air
Matyjaszewski, K. A., Dong, H., Jakubowski, W., et al. (2007) · Langmuir · doi:10.1021/la063402e · Cited by 682 · see citing works
Self-citationJakubowski, W., & Matyjaszewski, K. A. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200600272 · Cited by 671 · see citing works
Self-citationLiving alkene polymerization: New methods for the precision synthesis of polyolefins
Domski, G. J., Rose, J. M., Coates, G. W., Bolig, A. D., & Brookhart, M. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.11.001 · Cited by 663 · see citing works
Macromolecular architectures by living and controlled/living polymerizations
Hadjichristidis, N., Iatrou, H., Pitsikalis, M., & Mays, J. (2006) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.07.002 · Cited by 642 · see citing works
Smart polymeric gels: Redefining the limits of biomedical devices
Chaterji, S., Kwon, I. K., & Park, K. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2007.05.018 · Cited by 615 · see citing works
Controlled/living radical polymerization in aqueous dispersed systems
Cunningham, M. F. (2007) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2007.11.002 · Cited by 584 · see citing works
Polydispersity and block copolymer self-assembly
Lynd, N. A., Meuler, A. J., & Hillmyer, M. A. (2008) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2008.07.003 · Cited by 485 · see citing works
Min, K., Gao, H., & Matyjaszewski, K. (2005) · Journal of the American Chemical Society · doi:10.1021/ja0429364 · Cited by 471 · see citing works
Self-citationOh, J. K., Siegwart, D. J., Lee, H., Sherwood, G. A., Peteanu, L. A., Hollinger, J. O., Kataoka, K., & Matyjaszewski, K. A. (2007) · Journal of the American Chemical Society · doi:10.1021/ja069150l · Cited by 467 · see citing works
Self-citationXia, J., & Matyjaszewski, K. A. (1997) · Macromolecules · doi:10.1021/ma971009x · Cited by 454 · see citing works
Self-citationUse of ascorbic acid as reducing agent for synthesis of well-defined polymers by arget atrp
Min, K., Gao, H., & Matyjaszewski, K. (2007) · Macromolecules · doi:10.1021/ma0702041 · Cited by 380 · see citing works
Self-citationMechanistic transformations involving living and controlled/living polymerization methods
Yağcı, Y., & Taşdelen, M. A. (2006) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.07.003 · Cited by 339 · see citing works
Oh, J. K., Tang, C., Gao, H., Tsarevsky, N. V., & Matyjaszewski, K. A. (2006) · Journal of the American Chemical Society · doi:10.1021/ja060586a · Cited by 334 · see citing works
Self-citation(2007) · Wiley eBooks · doi:10.1002/9783527631421 · Cited by 330 · see citing works
Statistical, Gradient, Block, and Graft Copolymers by Controlled/Living Radical Polymerizations
Davis, K. A., & Matyjaszewski, K. (2007) · Springer eBooks · doi:10.1007/3-540-45806-9_1 · Cited by 325 · see citing works
Self-citationBelfield, K. D., Schafer, K. J., Liu, Y., Liu, J., Ren, X., & Stryland, E. W. V. (2000) · Journal of Physical Organic Chemistry · doi:10.1002/1099-1395(200012)13:12 · Cited by 272 · see citing works
Role of Cu0 in Controlled/“Living” Radical Polymerization
Matyjaszewski, K. A., Tsarevsky, N. V., Braunecker, W. A., Dong, H., Huang, J., Jakubowski, W., Kwak, Y., Nicolaÿ, R., Tang, W., & Yoon, J. A. (2007) · Macromolecules · doi:10.1021/ma0717800 · Cited by 271 · see citing works
Self-citationNanostructured Carbon Arrays from Block Copolymers of Polyacrylonitrile
Kowalewski, T., Tsarevsky, N. V., & Matyjaszewski, K. A. (2002) · Journal of the American Chemical Society · doi:10.1021/ja0178970 · Cited by 264 · see citing works
Self-citationRelationship between One‐Electron Transition‐Metal Reactivity and Radical Polymerization Processes
Poli, R. (2006) · Angewandte Chemie International Edition · doi:10.1002/anie.200503785 · Cited by 260 · see citing works
Lee, S. B., Russell, A. J., & Matyjaszewski, K. A. (2003) · Biomacromolecules · doi:10.1021/bm034126a · Cited by 255 · see citing works
Self-citationRoos, S. G., Müller, A. H. E., & Matyjaszewski, K. A. (1999) · Macromolecules · doi:10.1021/ma9819337 · Cited by 221 · see citing works
Self-citationControlled/“Living” Radical Polymerization of 2-(Dimethylamino)ethyl Methacrylate
Zhang, X. K., Xia, J., & Matyjaszewski, K. A. (1998) · Macromolecules · doi:10.1021/ma980477j · Cited by 213 · see citing works
Self-citationARGET ATRP of 2-(Dimethylamino)ethyl Methacrylate as an Intrinsic Reducing Agent
Dong, H., & Matyjaszewski, K. A. (2008) · Macromolecules · doi:10.1021/ma8017553 · Cited by 203 · see citing works
Self-citationMatyjaszewski, K. A., Gaynor, S. G., & Müller, A. H. E. (1997) · Macromolecules · doi:10.1021/ma970634z · Cited by 196 · see citing works
Self-citationDong, H., Tang, W., & Matyjaszewski, K. A. (2007) · Macromolecules · doi:10.1021/ma070424e · Cited by 194 · see citing works
Self-citationMatyjaszewski, K. A., Jo, S. M., Paik, H., & Shipp, D. A. (1999) · Macromolecules · doi:10.1021/ma9905526 · Cited by 190 · see citing works
Self-citationMatyjaszewski, K. A. (2003) · Polymer International · doi:10.1002/pi.1339 · Cited by 188 · see citing works
Self-citationTridentate Nitrogen-Based Ligands in Cu-Based ATRP: A Structure−Activity Study
Matyjaszewski, K. A., Göbelt, B., Paik, H., & Horwitz, C. P. (2001) · Macromolecules · doi:10.1021/ma001181s · Cited by 188 · see citing works
Self-citationBernaerts, K. V., & Prez, F. D. (2006) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.08.007 · Cited by 186 · see citing works
Shinoda, H., & Matyjaszewski, K. A. (2001) · Macromolecules · doi:10.1021/ma0105791 · Cited by 184 · see citing works
Self-citationMin, K., Gao, H., & Matyjaszewski, K. A. (2006) · Journal of the American Chemical Society · doi:10.1021/ja0629054 · Cited by 182 · see citing works
Self-citationImmobilization of the Copper Catalyst in Atom Transfer Radical Polymerization
Kickelbick, G., Paik, H., & Matyjaszewski, K. A. (1999) · Macromolecules · doi:10.1021/ma9818432 · Cited by 174 · see citing works
Self-citationYamago, S. (2005) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.21154 · Cited by 173 · see citing works
Introduction to living polymeriz. Living and/or controlled polymerization
Matyjaszewski, K. A. (1995) · Journal of Physical Organic Chemistry · doi:10.1002/poc.610080403 · Cited by 170 · see citing works
Self-citationMatyjaszewski, K., & Gaynor, S. G. (1997) · Macromolecules · doi:10.1021/ma970635r · Cited by 170 · see citing works
Self-citationHighly Controlled Living Radical Polymerization through Dual Activation of Organobismuthines
Yamago, S., Kayahara, E., Kotani, M., et al. (2007) · Angewandte Chemie International Edition · doi:10.1002/anie.200604473 · Cited by 166 · see citing works
Mechanisms and kinetics of living radical polymerizations
Fukuda, T., Goto, A., & Ohno, K. (2000) · Macromolecular Rapid Communications · doi:10.1002/(sici)1521-3927(200003)21:4 · Cited by 161 · see citing works
Mueller, L., Jakubowski, W., Tang, W., & Matyjaszewski, K. A. (2007) · Macromolecules · doi:10.1021/ma071130w · Cited by 161 · see citing works
Self-citationQin, S., Matyjaszewski, K., Xu, H. F., et al. (2003) · Macromolecules · doi:10.1021/ma021472w · Cited by 156 · see citing works
Self-citationCoca, S., Paik, H., & Matyjaszewski, K. A. (1997) · Macromolecules · doi:10.1021/ma970637b · Cited by 152 · see citing works
Self-citationZhang, X. K., & Matyjaszewski, K. A. (1999) · Macromolecules · doi:10.1021/ma981332f · Cited by 151 · see citing works
Self-citationPolystyrene with Improved Chain‐End Functionality and Higher Molecular Weight by ARGET ATRP
Jakubowski, W., Kırcı, B., Gil, R. R., & Matyjaszewski, K. A. (2007) · Macromolecular Chemistry and Physics · doi:10.1002/macp.200700425 · Cited by 151 · see citing works
Self-citationImproving the Structural Control of Graft Copolymers by Combining ATRP with the Macromonomer Method
Shinoda, H., Miller, P. J., & Matyjaszewski, K. A. (2001) · Macromolecules · doi:10.1021/ma001943j · Cited by 151 · see citing works
Self-citationNanda, A. K., & Matyjaszewski, K. (2003) · Macromolecules · doi:10.1021/ma0340107 · Cited by 148 · see citing works
Self-citationGaynor, S. G., & Matyjaszewski, K. (1997) · Macromolecules · doi:10.1021/ma970358o · Cited by 147 · see citing works
Self-citationMechanistic and Synthetic Aspects of Atom Transfer Radical Polymerization
Matyjaszewski, K. A. (1997) · Journal of Macromolecular Science Part A · doi:10.1080/10601329708010308 · Cited by 146 · see citing works
Self-citationBlock Copolymers by Transformation of “Living” Carbocationic into “Living” Radical Polymerization
Coca, S., & Matyjaszewski, K. A. (1997) · Macromolecules · doi:10.1021/ma970073b · Cited by 145 · see citing works
Self-citationAtom Transfer Radical Polymerization in Microemulsion
Min, K., & Matyjaszewski, K. A. (2005) · Macromolecules · doi:10.1021/ma051675v · Cited by 137 · see citing works
Self-citationMatyjaszewski, K. A. (1993) · Macromolecules · doi:10.1021/ma00059a048 · Cited by 134 · see citing works
Self-citationHighly Controlled Living Radical Polymerization through Dual Activation of Organobismuthines
Yamago, S., Kayahara, E., Kotani, M., et al. (2007) · Angewandte Chemie · doi:10.1002/ange.200604473 · Cited by 128 · see citing works
Chain-growth polycondensation: The living polymerization process in polycondensation
Yokozawa, T., & Yokoyama, A. (2006) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.08.001 · Cited by 126 · see citing works
Kajiwara, A., & Matyjaszewski, K. A. (1998) · Macromolecules · doi:10.1021/ma971445j · Cited by 101 · see citing works
Self-citationNicolaÿ, R., & Matyjaszewski, K. A. (2008) · Macromolecules · doi:10.1021/ma800539v · Cited by 96 · see citing works
Self-citationTang, H., Radosz, M., & Shen, Y. (2006) · Macromolecular Rapid Communications · doi:10.1002/marc.200600258 · Cited by 91 · see citing works
Kwak, Y., Nicolaÿ, R., & Matyjaszewski, K. A. (2008) · Macromolecules · doi:10.1021/ma801502s · Cited by 90 · see citing works
Self-citationKwak, Y., & Matyjaszewski, K. A. (2008) · Macromolecules · doi:10.1021/ma801231r · Cited by 74 · see citing works
Self-citationHolmes, P. F., Bohrer, M., & Kohn, J. (2008) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2008.05.002 · Cited by 67 · see citing works
Weiss, J. F., Tollin, G., & Yoke, J. T. (1964) · Inorganic Chemistry · doi:10.1021/ic50020a002 · Cited by 63 · see citing works
Huang, J., Pintauer, T., & Matyjaszewski, K. A. (2004) · Journal of Polymer Science Part A Polymer Chemistry · doi:10.1002/pola.20175 · Cited by 59 · see citing works
Self-citationKinetics and mechanism of aliphatic amine oxidation by aqueous (batho)2CuII
Wang, F., & Sayre, L. M. (1992) · Journal of the American Chemical Society · doi:10.1021/ja00027a032 · Cited by 53 · see citing works
Lode, U., Pomper, T., Karl, A., von Krosigk, G., Cunis, S., Wilke, W., & Gehrke, R. (1998) · Macromolecular Rapid Communications · doi:10.1002/(sici)1521-3927(19980101)19:1 · Cited by 27 · see citing works
Mechanism for the Reduction of the Mixed-Valent MnIIIMnIV[2-OHsalpn]2+ Complex by Tertiary Amines
Caudle, M. T., & Pecoraro, V. L. (2000) · Inorganic Chemistry · doi:10.1021/ic000727o · Cited by 21 · see citing works
A convenient route to poly(methylphenylsilane)‐graft‐polystyrene copolymers
Jones, R. G., & Holder, S. J. (1997) · Macromolecular Chemistry and Physics · doi:10.1002/macp.1997.021981120 · Cited by 20 · see citing works
Lutsen, L., Cordina, G., Jones, R. G., et al. (1998) · European Polymer Journal · doi:10.1016/s0014-3057(98)00041-x · Cited by 15 · see citing works
Grafting on polysilanes using atom transfer radical polymerisation
dos Santos, C. G., Parker, J., Jones, R. G., et al. (2002) · Polymer International · doi:10.1002/pi.859 · Cited by 4 · see citing works
Cationic Ring-Opening Polymerization(CROP) major mechanistic phenomena
Penczek, S. (2000) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/(sici)1099-0518(20000601)38:11
Controlled free radical ring-opening polymerization and chain extension of the living polymer
Wei, Y., Connors, E. J., Jia, X., & Wang, C. (1998) · Journal of Polymer Science Part A: Polymer Chemistry · doi:10.1002/(sici)1099-0518(19980415)36:5
Flagged first, then by citations
Cited by
Sorted by citations
Block Copolymers: Synthesis, Self-Assembly, and Applications
Feng, H., Lu, X., Wang, W., Kang, N.-G., & Mays, J. (2017) · Polymers · doi:10.3390/polym9100494 · Cited by 467 · see citing works
“Later on, miniemulsion ARGET ATRP was developed by the same group and used for the preparation of homopolymers and block copolymers [26,27].”
Method
- Authors
- Kwak, Y., & Matyjaszewski, K.
- Affiliations
- Carnegie Mellon University (US)
- Corresponding author
- Matyjaszewski, Krzysztof
- Venue
- Polymer International
- Publisher
- Wiley
- Published
- 2009-01-21
- Volume
- 58
- Issue
- 3
- Pages
- 242-247
- ISSN
- 0959-8103 (ISSN-L)
- 1097-0126
- OpenAlex
- W2014243182
- Semantic Scholar
- 3ca71ef639c2e1744b2ecf979ef72c158d27b532
- Cited by
- 159
- References
- 89
- Citations by year
- 2026: 5 · 2025: 4 · 2024: 8 · 2023: 2 · 2022: 6 · 2021: 8 · 2020: 6 · 2019: 11 · 2018: 11 · 2017: 12 · 2016: 13 · 2015: 10 · 2014: 7 · 2013: 13 · 2012: 13
- FWCI
- 6.93
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Polymer International (publishedVersion)
- Funders
- National Science Foundation
- Carnegie Mellon University
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Physical Sciences › Chemistry › Organic Chemistry › Radical Photochemical Reactions
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Keywords
- ARGET ATRP, atom transfer radical polymerization, methyl methacrylate, poly(methyl methacrylate), nitrogen-based ligands, reducing agents, chain extension, polydispersity index, end-group functionality
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review