Nanostructured functional materials prepared by atom transfer radical polymerization

Nature Chemistry

Volumn 1, Issue 4, 2009, Pages 276-288

  Matyjaszewski, Krzysztof ^a   Tsarevsky, Nicolay V ^b  

^a CARNEGIE MELLON UNIVERSITY   (United States)

^b ATRP Solutions Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOMATERIAL; BIOPOLYMER; FREE RADICAL; NANOMATERIAL; POLYMER;

ARTICLE; BIOENGINEERING; CHEMISTRY; METHODOLOGY; SYNTHESIS;

BIOCOMPATIBLE MATERIALS; BIOENGINEERING; BIOPOLYMERS; FREE RADICALS; NANOSTRUCTURES; POLYMERS;

EID: 67949112461     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.257     Document Type: Article

References (102)

1. Szwarc, M. 'Living' polymers. Nature 176, 1168-1169 (1956).
2. Matyjaszewski, K. & Davis, T. P. (eds) Handbook of Radical Polymerization (Wiley, 2002).
3. Braunecker, W. A. & Matyjaszewski, K. Controlled/living radical polymerization: Features, developments, and perspectives. Prog. Polym. Sci. 32, 93-146 (2007).
4. Wang, J.?S. & Matyjaszewski, K. Controlled/'living' radical polymerization. Atom transfer radical polymerization in the presence of transition?metal complexes. J. Am. Chem. Soc. 117, 5614-5615 (1995).
5. Matyjaszewski, K. & Xia, J. Atom transfer radical polymerization. Chem. Rev. 101, 2921-2990 (2001).
6. Kamigaito, M., Ando, T. & Sawamoto, M. Metal?catalyzed living radical polymerization. Chem. Rev. 101, 3689 (2001).
7. Tsarevsky, N. V. & Matyjaszewski, K. 'Green' atom transfer radical polymerization: From process design to preparation of well?defned environmentally?friendly polymeric materials. Chem. Rev. 107, 2270-2299 (2007).
8. Hawker, C. J., Bosman, A. W. & Harth, E. New polymer synthesis by nitroxide mediated living radical polymerizations. Chem. Rev. 101, 3661-3688 (2001).
9. Moad, G., Rizzardo, E. & Tang, S. H. Living radical polymerization by the RAFT process. Aust. J. Chem. 58, 379-410 (2005).
10. Shen, Y. , Tang, H. & Ding, S. Catalyst separation in atom transfer radical polymerization. Prog. Polym. Sci. 29, 1053-1078 (2004).
11. Fischer, H. Te persistent radical efect: A principle for selective radical reactions and living radical polymerizations. Chem. Rev. 101, 3581-3610 (2001).
12. Matyjaszewski, K. et al. Diminishing catalyst concentration in atom transfer radical polymerization with reducing agents. Proc. Natl Acad. Sci. USA 103, 15309-15314 (2006).
13. Jakubowski, W. & Matyjaszewski, K. Activators regenerated by electron transfer for atom transfer radical polymerization of (meth)acrylates and related block copolymers. Angew. Chem. Int. Ed. 45, 4482-4486 (2006).
14. Jakubowski, W. , Min, K. & Matyjaszewski, K. Activators regenerated by electron transfer for atom transfer radical polymerization of styrene. Macromolecules 39, 39-45 (2006).
15. Pintauer, T. & Matyjaszewski, K. Atom transfer radical addition and polymerization reactions catalyzed by ppm amounts of copper complexes. Chem. Soc. Rev. 37, 1087-1097 (2008).
16. Grubbs, R. H. Olefn?metathesis catalysts for the preparation of molecules and materials (Nobel lecture). Angew. Chem. Int. Ed. 45, 3760-3765 (2006).
17. Davis, K. A. & Matyjaszewski, K. Statistical, gradient, and segmented copolymers by controlled/living radical polymerizations. Adv. Polym. Sci. 159, 1-157 (2002).
18. Matyjaszewski, K. & Spanswick, J. Controlled/living radical polymerization. Mater. Today 8, 26-33 (2005).
19. Matyjaszewski, K., Ziegler, M. J., Arehart, S. V. , Greszta, D. & Pakula, T. Gradient copolymers by atom transfer radical copolymerization. J. Phys. Org. Chem. 13, 775-786 (2000).
20. Coessens, V. , Pintauer, T. & Matyjaszewski, K. Functional polymers by atom transfer radical polymerization. Prog. Polym. Sci. 26, 337-377 (2001).
21. Pyun, J. & Matyjaszewski, K. Synthesis of nanocomposite organic/inorganic hybrid materials using controlled/ 'living' radical polymerization. Chem. Mater. 13, 3436-3448 (2001).
22. Percec, V. et al. Aqueous room temperature metal-catalyzed living radical polymerization of vinyl chloride. J. Am. Chem. Soc. 124, 4940-4941 (2002).
23. Kwak, Y., Nicolay, R. & Matyjaszewski, K. Concurrent ATRP/RAFT of styrene and methyl methacrylate with dithioesters catalyzed by copper(i) complexes. Macromolecules 41, 6602-6604 (2008).
24. Bates, F. S. & Fredrickson, G. H. Block copolymers: Designer sof materials. Phys. Today 52, 32 (February 1999).
25. Foerster, S. & Plantemberg, T. From self-organizing polymers to nanohybrid and biomaterials. Angew. Chem. Int. Ed. 41, 688-714 (2002).
26. Lynd, N. A., Meuler, A. J. & Hillmyer, M. A. Polydispersity and block copolymer self-assembly. Prog. Polym. Sci. 33, 875-893 (2008).
27. Listak, J. et al. Efect of symmetry of molecular weight distribution in block copolymers on formation of 'metastable' morphologies. Macromolecules 41, 5919-5927 (2008).
28. Matyjaszewski, K., Gnanou, Y. & Leibler, L. Macromolecular Engineering: Precise Synthesis, Materials Properties, Applications (Wiley-VCH, 2007).
29. Foerster, S., Abetz, V. & Mueller, A. H. E. Polyelectrolyte block copolymer micelles. Adv. Polym. Sci. 166, 173-210 (2004).
30. O'Reilly, R. K., Hawker, C. J. & Wooley, K. L. Crosslinked block copolymer micelles: functional nanostructures of great potential and versatility. Chem. Soc. Rev. 35, 1068-1083 (2006).
31. Read, E. S. & Armes, S. P. Recent advances in shell cross-linked micelles. Chem. Commun. 3021-3055 (2007).
32. Lobb, E. J., Ma, I., Billingham, N. C., Armes, S. P. & Lewis, A. L. Facile synthesis of well-defned, biocompatible phosphorylcholine-based methacrylate copolymers via atom transfer radical polymerization at 20°C. J. Am. Chem. Soc. 123, 7913-7914 (2001).
33. Hadjichristidis, N., Iatrou, H., Pitsikalis, M. & Mays, J. Macromolecular architectures by living and controlled/living polymerizations. Prog. Polym. Sci. 31, 1068-1132 (2006).
34. Matyjaszewski, K. Te synthesis of functional star copolymers as an illustration of the importance of controlling polymer structures in the design of new materials. Polym. Int. 52, 1559 (2003).
35. Gao, C. & Yan, D. Hyperbranched polymers: From synthesis to applications. Prog. Polym. Sci. 29, 183-275 (2004).
36. Peleshanko, S. & Tsukruk, V. V. Te architectures and surface behavior of highly branched molecules. Prog. Polym. Sci. 33, 523-580 (2008).
37. Frechet, J. M. J. et al. Self-condensing vinyl polymerization: An approach to dendritic materials. Science 269, 1080-1083 (1995).
38. Gao, H. & Matyjaszewski, K. Synthesis of functional polymers with controlled architecture by CRP of monomers in the presence of cross-linkers: From stars to gels. Prog. Polym. Sci. 34, 317-350 (2009).
39. Ide, N. & Fukuda, T. Nitroxide-controlled free-radical copolymerization of vinyl and divinyl monomers. Evaluation of pendant-vinyl reactivity. Macromolecules 30, 4268-4271 (1997).
40. Tsarevsky, N. V. & Matyjaszewski, K. Combining atom transfer radical polymerization and disulfde/thiol redox chemistry: A route to well-defned (bio)degradable polymeric materials. Macromolecules 38, 3087-3092 (2005).
41. Gao, H., Ohno, S. & Matyjaszewski, K. Low polydispersity star polymers via cross-linking macromonomers by ATRP. J. Am. Chem. Soc. 128, 15111-15113 (2006).
42. Gao, H., Li, W. & Matyjaszewski, K. Synthesis of polyacrylate networks by ATRP: Parameters infuencing experimental gel points. Macromolecules 41, 2335-2340 (2008).
43. Tsarevsky, N. V., Bencherif, S. A. & Matyjaszewski, K. Graf copolymers by a combination of ATRP and two diferent consecutive click reactions. Macromolecules 40, 4439-4445 (2007).
44. Gao, H. & Matyjaszewski, K. Synthesis of molecular brushes by 'grafing onto' method: Combination of ATRP and click reactions. J. Am. Chem. Soc. 129, 6633-6639 (2007).
45. Matyjaszewski, K., Beers, K. L., Kern, A. & Gaynor, S. G. Hydrogels by atom transfer radical polymerization. I. Poly(N-vinylpyrrolidinone-g-styrene) via the macromonomer method. J. Polym. Sci. A 36, 823-830 (1998).
46. Sheiko, S. S., Sumerlin, B. S. & Matyjaszewski, K. Cylindrical molecular brushes: Synthesis, characterization, and properties. Prog. Polym. Sci. 33, 759-785 (2008).
47. Tsujii, Y., Ohno, K., Yamamoto, S., Goto, A. & Fukuda, T. Structure and properties of high-density polymer brushes prepared by surface-initiated living radical polymerization. Adv. Polym. Sci. 197, 1-45 (2006).
48. Yagci, Y. & Tasdelen, M. A. Mechanistic transformations involving living and controlled/living polymerization methods. Prog. Polym. Sci. 31, 1133-1170 (2006).
49. Lutz, J.-F. & Boerner, H. G. Modern trends in polymer bioconjugates design. Prog. Polym. Sci. 33, 1-39 (2008).
50. Ohno, K., Koh, K., Tsujii, Y. & Fukuda, T. Fabrication of ordered arrays of gold nanoparticles coated with high-density polymer brushes. Angew. Chem. Int. Ed. 42, 2751-2754 (2003).
51. Kolb, H. C., Finn, M. G. & Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004-2021 (2001).
52. Golas, P. L. & Matyjaszewski, K. Click chemistry and ATRP: A benefcial union for the preparation of functional materials. QSAR Combinat. Sci. 26, 1116-1134 (2007).
53. Hoyle, C. E., Lee, T. Y. & Roper, T. Tiol-enes: Chemistry of the past with promise for the future. J. Polym. Sci. A 42, 5301-5338 (2004).
54. Davis, K. A., Charleux, B. & Matyjaszewski, K. Preparation of block copolymers of polystyrene and poly(t-butyl acrylate) of various molecular weights and architectures by atom transfer radical polymerization. J. Polym. Sci. A 38, 2274-2283 (2000).
55. Van Camp, W., Du Prez, F. E. & Bon, S. A. F. Atom transfer radical polymerization of 1-ethoxyethyl (meth)acrylate: Facile route toward near-monodisperse poly((meth)acrylic acid). Macromolecules 37, 6673-6675 (2004).
56. Cai, Y. & Armes, S. P. Synthesis of well-defned Y-shaped zwitterionic block copolymers via atom-transfer radical polymerization. Macromolecules 38, 271-279 (2005).
57. Tsarevsky, N. V. , Bernaerts, K. V. , Dufour, B., Du Prez, F. E. & Matyjaszewski, K. Well-defned (co)polymers with 5-vinyltetrazole units via combination of atom transfer radical (co)polymerization of acrylontrile and 'click chemistry'-type postpolymerization modifcation. Macromolecules 37, 9308-9313 (2004).
58. Tsarevsky, N. V. & Matyjaszewski, K. Reversible redox cleavage/coupling of polystyrene with disulfde or thiol groups prepared by atom transfer radical polymerization. Macromolecules 35, 9009-9014 (2002).
59. Bontempo, D., Heredia, K. L., Fish, B. A. & Maynard, H. D. Cysteine-reactive polymers synthesized by atom transfer radical polymerization for conjugation to proteins. J. Am. Chem. Soc. 126, 15372 (2004).
60. Qi, K., Ma, Q., Remsen, E. E., Clark, C. G. & Wooley, K. L. Determination of the bioavailability of biotin conjugated onto shell cross-linked (SCK) nanoparticles. J. Am. Chem. Soc. 126, 6599-6607 (2004).
61. Matyjaszewski, K., Nakagawa, Y. & Gaynor, S. G. Synthesis of well-defned azido and amino-endfunctionalized polystyrene by atom transfer radical polymerization. Macromol. Rapid Commun. 18, 1057-1066 (1997).
62. Haddleton, D. M. & Ohno, K. Well-defned oligosaccharide-terminated polymers from living radical polymerization. Biomacromolecules 1, 152-156 (2000).
63. Rettig, H., Krause, E. & Boerner, H. G. Atom transfer radical polymerization with polypeptide initiators: A general approach to block copolymers of sequence-defned polypeptides and synthetic polymers. Macromol. Rapid Commun. 25, 1251-1256 (2004).
64. Ayres, L., Adams, P. H. H. M., Loewik, D. W. P. M. & Van Hest, J. C. M. Beta-sheet side chain polymers synthesized by atom-transfer radical polymerization. Biomacromolecules 6, 825-831 (2005).
65. Heredia, K. L. et al. In situ preparation of protein-'smart' polymer conjugates with retention of bioactivity. J. Am. Chem. Soc. 127, 16955-16960 (2005).
66. Wang, Y., Armitage, B. A. & Berry, G. C. Reversible association of PNA-terminated poly(2-hydroxyethyl acrylate) from ATRP. Macromolecules 38, 5846-5848 (2005).
67. Nicolas, J., San Miguel, V. , Mantovani, G. & Haddleton, D. M. Fluorescently tagged polymer bioconjugates from protein derived macroinitiators. Chem. Commun. 4697-4699 (2006).
68. Geng, J. et al. Site-directed conjugation of 'clicked' glycopolymers to form glycoprotein mimics: Binding to mammalian lectin and induction of immunological function. J. Am. Chem. Soc. 129, 15156-15163 (2007).
69. Ohno, K., Tsujii, Y. & Fukuda, T. Synthesis of a well-defned glycopolymer by atom transfer radical polymerization. J. Polym. Sci. A 36, 2473-2481 (1998).
70. Ayres, L., Vos, M. R. J., Adams, P. J. H. M., Shklyarevskiy, I. O. & Van Hest, J. C. M. Elastin-based side-chain polymers synthesized by ATRP. Macromolecules 36, 5967-5973 (2003).
71. Nicolas, J., Mantovani, G. & Haddleton, D. M. Living radical polymerization as a tool for the synthesis of polymer-protein/peptide bioconjugates. Macromol. Rapid Commun. 28, 1083-1111 (2007).
72. Gao, H., Tsarevsky, N. V. & Matyjaszewski, K. Synthesis of degradable miktoarm star copolymers via atom transfer radical polymerization. Macromolecules 38, 5995-6004 (2005).
73. Oh, J. K., Drumright, R., Siegwart, D. J. & Matyjaszewski, K. Te development of microgels/nanogels for drug delivery applications. Prog. Polym. Sci. 33, 448-477 (2008).
74. Tiller, J. C., Liao, C. J., Lewis, K. & Klibanov, A. M. Designing surfaces that kill bacteria on contact. Proc. Natl Acad. Sci. USA 98, 5981-5985 (2001).
75. Lee, S. B. et al. Permanent, nonleaching antibacterial surfaces. 1. Synthesis by atom transfer radical polymerization. Biomacromolecules 5, 877-882 (2004).
76. Murata, H., Koepsel, R. R., Matyjaszewski, K. & Russell, A. J. Permanent, non-leaching antibacterial surfaces. 2. How high density cationic surfaces kill bacterial cells. Biomaterials 28, 4870-4879 (2007).
77. Huang, J. et al. Nonleaching antibacterial glass surfaces via 'grafing onto': Te efect of the number of quaternary ammonium groups on biocidal activity. Langmuir 24, 6785-6795 (2008).
78. Ayres, L. et al. Synthesis and controlled polymerisation of a novel gramicidin S analogue. Macromol. Rapid Commun. 26, 1336-1340 (2005).
79. Iwata, R., Satoh, R., Iwasaki, Y. & Akiyoshi, K. Covalent immobilization of antibody fragments on well-defned polymer brushes via site-directed method. Colloids Surf. B 62, 288-298 (2008).
80. Opsteen, J. A. & van Hest, J. C. M. in Macromolecular Engineering: Precise Synthesis, Materials Properties, Applications (eds Matyjaszewski, K., Gnanou, Y. & Leibler, L.) 2645-2687 (Wiley-VCH, 2007).
81. Lutz, J.-F. Polymerization of oligo(ethylene glycol) (meth)acrylates: Toward new generations of smart biocompatible materials. J. Polym. Sci. A. 46, 3459-3470 (2008).
82. Pyun, J., Kowalewski, T. & Matyjaszewski, K. Synthesis of polymer brushes using atom transfer radical polymerization. Macromol. Rapid Commun. 24, 1043-1059 (2003).
83. Matyjaszewski, K. et al. Polymers at interfaces: Using atom transfer radical polymerization in the controlled growth of homopolymers and block copolymers from silicon surfaces in the absence of untethered sacrifcial initiator. Macromolecules 32, 8716-8724 (1999).
84. Bombalski, L., Dong, H., Listak, J., Matyjaszewski, K. & Bockstaller, M. R. Null-scattering hybrid particles using controlled radical polymerization. Adv. Mater. 19, 4486-4490 (2007).
85. McCarthy, P. et al. Nanoengineered analytical immobilized metal afnity chromatography stationary phase by atom transfer radical polymerization: Separation of synthetic prion peptides. Anal. Biochem. 366, 1-8 (2007).
86. Wu, W. et al. 'Hairy' single-walled carbon nanotubes prepared by atom transfer radical polymerization. Small 3, 1803-1810 (2007).
87. Gao, C., Vo, C. D., Jin, Y. Z., Li, W. & Armes, S. P. Multihydroxy polymer-functionalized carbon nanotubes: synthesis, derivatization, and metal loading. Macromolecules 38, 8634-8648 (2005).
88. Yang, J., Li, L. & Wang, C. Synthesis of a water soluble, monosubstituted C60 polymeric derivative and its photoconductive properties. Macromolecules 36, 6060-6065 (2003).
89. Alexandre, M. & Dubois, P. in Macromolecular Engineering: Precise Synthesis, Materials Properties, Applications (eds Matyjaszewski, K., Gnanou, Y. & Leibler, L.) 2033-2070 (Wiley-VCH, 2007).
90. Dong, H. et al. One-pot synthesis of robust core/shell gold nanoparticles. J. Am. Chem. Soc. 130, 12852-12853 (2008).
91. Mecerreyes, D., Pomposo, J. A., Bengoetxea, M. & Grande, H. Novel pyrrole end-functional macromonomers prepared by ring-opening and atom-transfer radical polymerizations. Macromolecules 33, 5846-5849 (2000).
92. Economopoulos, S. P. et al. Novel brush-type copolymers bearing thiophene backbone and side chain quinoline blocks. Synthesis and their use as a compatibilizer in thiophene-quinoline polymer blends. Macromolecules 40, 921-927 (2007).
93. Kowalewski, T., McCullough, R. D. & Matyjaszewski, K. Complex nanostructured materials from segmented copolymers prepared by ATRP. Eur. Phys. J. E 10, 5-16 (2003).
94. Yoo, J. E., Bucholz, T. L., Jung, S. & Loo, Y.-L. Narrowing the size distribution of the polymer acid improves PANI conductivity. J. Mater. Chem. 18, 3129-3135 (2008).
95. McCullough, L. A. et al. Templating conducting polymers via self-assembly of block copolymers and supramolecular recognition. Macromolecules 40, 7745-7747 (2007).
96. Kowalewski, T., Tsarevsky, N. V. & Matyjaszewski, K. Nanostructured carbon arrays from block copolymers of polyacrylonitrile. J. Am. Chem. Soc. 124, 10632-10633 (2002).
97. Aimi, J., McCullough, L. A. & Matyjaszewski, K. Synthesis of poly(vinylacetylene) block copolymers by atom transfer radical polymerization. Macromolecules 41, 9522-9524 (2008).
98. Tang, C. et al. Long-range ordered thin flms of block copolymers prepared by zone-casting and their thermal conversion into ordered nanostructured carbon. J. Am. Chem. Soc. 127, 6918-6919 (2005).
99. Esteves, A. C. C., Bombalski, L., Trindade, T., Matyjaszewski, K. & Barros-Timmons, A. Polymer grafing from CdS quantum dots via AGET ATRP in miniemulsion. Small 3, 1230-1236 (2007).
100. Neugebauer, D., Zhang, Y. , Pakula, T., Sheiko, S. S. & Matyjaszewski, K. Densely-grafed and double-grafed PEO brushes via ATRP. A route to sof elastomers. Macromolecules 36, 6746-6755 (2003).
101. Zhang, Y. et al. Super sof elastomers as ionic conductors. Polymer 45, 6333-6339 (2004).
102. Xu, Y. et al. Double-grafed cylindrical brushes: Synthesis and characterization of poly(lauryl methacrylate) brushes. Macromol. Chem. Phys. 208, 1666-1675 (2007).