Exploiting Metalloporphyrins for Selective Living Radical Polymerization Tunable over Visible Wavelengths

Journal of the American Chemical Society

Volumn 137, Issue 28, 2015, Pages 9174-9185

  Shanmugam, Sivaprakash ^a   Xu, Jiangtao ^a,b   Boyer, Cyrille ^a,b  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ATOM TRANSFER RADICAL POLYMERIZATION; DISEASE CONTROL; DISEASES; FREE RADICAL POLYMERIZATION; FREE RADICAL REACTIONS; PHOTODYNAMIC THERAPY; POLYETHYLENE TEREPHTHALATES; POLYMERS; PORPHYRINS; SOLAR ENERGY; STYRENE; ZINC;

DERMATOLOGICAL DISEASE; LIVING RADICAL POLYMERIZATION; PHOTO-INDUCED ELECTRON TRANSFER; PHOTODYNAMIC THERAPY (PDT); POLYMERIZATION RATES; REVERSIBLE ADDITION FRAGMENTATION CHAIN TRANSFER; VISIBLE-LIGHT IRRADIATION; ZINC TETRAPHENYLPORPHINE;

LIVING POLYMERIZATION;

ACRYLAMIDE DERIVATIVE; ACRYLIC ACID DERIVATIVE; ACRYLIC ACID METHYL ESTER; BENZOIC ACID; DITHIOBENZOATE; DITHIOCARBAMIC ACID; METALLOPORPHYRIN; OXYGEN; PORPHYRIN; STYRENE; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE; ZINC TETRAPHENYLPORPHINE; METHACRYLAMIDE; METHACRYLIC ACID DERIVATIVE; THIOKETONE; TRITHIOCARBONIC ACID;

ARTICLE; BLUE LIGHT; CATALYST; COMPARATIVE STUDY; CONTROLLED STUDY; ELECTRON TRANSPORT; LIGHT; MOLECULAR WEIGHT; PHOTODYNAMIC THERAPY; POLYMERIZATION; QUANTUM YIELD; RED LIGHT; ROOM TEMPERATURE; SOLAR ENERGY; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION; RADIATION RESPONSE;

ACRYLAMIDES; CATALYSIS; LIGHT; METALLOPORPHYRINS; METHACRYLATES; OXIDATION-REDUCTION; POLYMERIZATION; STYRENE; THIONES;

EID: 84937710861     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b05274     Document Type: Article

References (126)

1. Kahn, K.; Plaxco, K. In Recognition Receptors in Biosensors; Zourob, M., Ed.; Springer: New York, 2010; pp 3-45.
2. Baron, R.; McCammon, J. A. Annu. Rev. Phys. Chem. 2013, 64, 151-175 10.1146/annurev-physchem-040412-110047
3. Woo, S.; Rothemund, P. W. K. Nat. Chem. 2011, 3, 620-627 10.1038/nchem.1070
4. Matyjaszewski, K.; Tsarevsky, N. V. J. Am. Chem. Soc. 2014, 136, 6513-6533 10.1021/ja408069v
5. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688 10.1021/cr990119u
6. Moad, G.; Rizzardo, E.; Thang, S. H. Chem.-Asian J. 2013, 8, 1634-1644 10.1002/asia.201300262
7. Buchler, J. W. In The Porphyrins; Dolphin, D., Ed.; Academic Press: Waltham, MA, 1978; pp 389-483.
8. Zhao, Y.; Yu, M.; Fu, X. Chem. Commun. 2013, 49, 5186-5188 10.1039/c3cc41466c
9. Hsu, C.-S.; Yang, T.-Y.; Peng, C.-H. Polym. Chem. 2014, 5, 3867-3875 10.1039/C4PY00191E
10. Zhao, Y.; Yu, M.; Zhang, S.; Liu, Y.; Fu, X. Macromolecules 2014, 47, 6238-6245 10.1021/ma5014385
11. Peng, C.-H.; Li, S.; Wayland, B. B. J. Chin. Chem. Soc. 2009, 56, 219-233 10.1002/jccs.200900032
12. Shanmugam, S.; Xu, J.; Boyer, C. Chem. Sci. 2015, 6, 1341-1349 10.1039/C4SC03342F
13. Kang, J. S.; Kim, J.-S. J. Biol. Chem. 2000, 275, 8742-8748 10.1074/jbc.275.12.8742
14. Xu, J.; Jung, K.; Atme, A.; Shanmugam, S.; Boyer, C. J. Am. Chem. Soc. 2014, 136, 5508-5519 10.1021/ja501745g
15. Shanmugam, S.; Xu, J.; Boyer, C. Macromolecules 2014, 47, 4930-4942 10.1021/ma500842u
16. Xu, J.; Jung, K.; Boyer, C. Macromolecules 2014, 47, 4217-4229 10.1021/ma500883y
17. Xu, J.; Jung, K.; Corrigan, N. A.; Boyer, C. Chem. Sci. 2014, 5, 3568-3575 10.1039/C4SC01309C
18. Xu, J.; Shanmugam, S.; Duong, H. T.; Boyer, C. Polym. Chem. 2015, 10.1039/C4PY01317D
19. Fu, C.; Xu, J.; Tao, L.; Boyer, C. ACS Macro Lett. 2014, 3, 633-638 10.1021/mz500245k
20. Anastasaki, A.; Nikolaou, V.; Zhang, Q.; Burns, J.; Samanta, S. R.; Waldron, C.; Haddleton, A. J.; McHale, R.; Fox, D.; Percec, V.; Wilson, P.; Haddleton, D. M. J. Am. Chem. Soc. 2014, 136, 1141-1149 10.1021/ja411780m
21. Anastasaki, A.; Nikolaou, V.; Simula, A.; Godfrey, J.; Li, M.; Nurumbetov, G.; Wilson, P.; Haddleton, D. M. Macromolecules 2014, 47, 3852-3859 10.1021/ma500787d
22. Konkolewicz, D.; Schröder, K.; Buback, J.; Bernhard, S.; Matyjaszewski, K. ACS Macro Lett. 2012, 1, 1219-1223 10.1021/mz300457e
23. Ribelli, T. G.; Konkolewicz, D.; Bernhard, S.; Matyjaszewski, K. J. Am. Chem. Soc. 2014, 136, 13303-13312 10.1021/ja506379s
24. Ribelli, T. G.; Konkolewicz, D.; Pan, X.; Matyjaszewski, K. Macromolecules 2014, 47, 6316-6321 10.1021/ma501384q
25. Xiao, P.; Dumur, F.; Zhang, J.; Gigmes, D.; Fouassier, J. P.; Lalevee, J. Polym. Chem. 2014, 5, 6350-6357 10.1039/C4PY00925H
26. Kwak, Y.; Matyjaszewski, K. Macromolecules 2010, 43, 5180-5183 10.1021/ma100850a
27. Pan, X.; Lamson, M.; Yan, J.; Matyjaszewski, K. ACS Macro Lett. 2015, 4, 192-196 10.1021/mz500834g
28. Tasdelen, M. A.; Uygun, M.; Yagci, Y. Macromol. Rapid Commun. 2011, 32, 58-62 10.1002/marc.201000351
29. Tasdelen, M. A.; Uygun, M.; Yagci, Y. Macromol. Chem. Phys. 2010, 211, 2271-2275 10.1002/macp.201000445
30. Zhang, T.; Chen, T.; Amin, I.; Jordan, R. Polym. Chem. 2014, 5, 4790-4796 10.1039/C4PY00346B
31. Yang, Q.; Dumur, F.; Morlet-Savary, F.; Poly, J.; Lalevée, J. Macromolecules 2015, 48, 1972-1980 10.1021/ma502384y
32. Anastasaki, A.; Nikolaou, V.; McCaul, N. W.; Simula, A.; Godfrey, J.; Waldron, C.; Wilson, P.; Kempe, K.; Haddleton, D. M. Macromolecules 2015, 48, 1404-1411 10.1021/acs.macromol.5b00058
33. Wenn, B.; Conradi, M.; Carreiras, A. D.; Haddleton, D. M.; Junkers, T. Polym. Chem. 2014, 5, 3053-3060 10.1039/C3PY01762A
34. Chuang, Y.-M.; Ethirajan, A.; Junkers, T. ACS Macro Lett. 2014, 3, 732-737 10.1021/mz5003867
35. Nikolaou, V.; Anastasaki, A.; Alsubaie, F.; Simula, A.; Fox, D. J.; Haddleton, D. M. Polym. Chem. 2015, 6, 3581-3585 10.1039/C5PY00406C
36. Fors, B. P.; Hawker, C. J. Angew. Chem., Int. Ed. 2012, 51, 8850-8853 10.1002/anie.201203639
37. Fors, B. P.; Poelma, J. E.; Menyo, M. S.; Robb, M. J.; Spokoyny, D. M.; Kramer, J. W.; Waite, J. H.; Hawker, C. J. J. Am. Chem. Soc. 2013, 135, 14106-14109 10.1021/ja408467b
38. Treat, N. J.; Fors, B. P.; Kramer, J. W.; Christianson, M.; Chiu, C.-Y.; Alaniz, J. R. d.; Hawker, C. J. ACS Macro Lett. 2014, 3, 580-584 10.1021/mz500242a
39. Lalevée, J.; Tehfe, M.-A.; Dumur, F.; Gigmes, D.; Blanchard, N.; Morlet-Savary, F.; Fouassier, J. P. ACS Macro Lett. 2012, 1, 286-290 10.1021/mz2001753
40. Versace, D.-L.; Cerezo Bastida, J.; Lorenzini, C.; Cachet-Vivier, C.; Renard, E.; Langlois, V.; Malval, J.-P.; Fouassier, J.-P.; Lalevée, J. Macromolecules 2013, 46, 8808-8815 10.1021/ma4019872
41. Zhang, G.; Song, I. Y.; Ahn, K. H.; Park, T.; Choi, W. Macromolecules 2011, 44, 7594-7599 10.1021/ma201546c
42. Chen, Y.; Hu, Z.; Xu, D.; Yu, Y.; Tang, X.; Guo, H. Macromol. Chem. Phys. 2015, 216, 1055-1060 10.1002/macp.201500006
43. Treat, N. J.; Sprafke, H.; Kramer, J. W.; Clark, P. G.; Barton, B. E.; Read de Alaniz, J.; Fors, B. P.; Hawker, C. J. J. Am. Chem. Soc. 2014, 136, 16096-16101 10.1021/ja510389m
44. Shanmugam, S.; Xu, J.; Boyer, C. Chem. Sci. 2015, 6, 1341-1349 10.1039/C4SC03342F
45. Ohtsuki, A.; Lei, L.; Tanishima, M.; Goto, A.; Kaji, H. J. Am. Chem. Soc. 2015, 137, 5610-5617 10.1021/jacs.5b02617
46. Chen, M.; MacLeod, M. J.; Johnson, J. A. ACS Macro Lett. 2015, 4, 566-569 10.1021/acsmacrolett.5b00241
47. Miyake, G. M.; Theriot, J. C. Macromolecules 2014, 47, 8255-8261 10.1021/ma502044f
48. Ogawa, K. A.; Goetz, A. E.; Boydston, A. J. J. Am. Chem. Soc. 2015, 137, 1400-1403 10.1021/ja512073m
49. Chen, M.; Johnson, J. A. Chem. Commun. 2015, 51, 6742-6745 10.1039/C5CC01562F
50. Zhao, Y.; Yu, M.; Zhang, S.; Wu, Z.; Liu, Y.; Peng, C.-H.; Fu, X. Chem. Sci. 2015, 6, 2979-2988 10.1039/C5SC00477B
51. Matyjaszewski, K.; Dong, H.; Jakubowski, W.; Pietrasik, J.; Kusumo, A. Langmuir 2007, 23, 4528-4531 10.1021/la063402e
52. Williams, V. A.; Ribelli, T. G.; Chmielarz, P.; Park, S.; Matyjaszewski, K. J. Am. Chem. Soc. 2015, 137, 1428-1431 10.1021/ja512519j
53. Fleischmann, S.; Rosen, B. M.; Percec, V. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 1190-1196 10.1002/pola.23879
54. Nguyen, N. H.; Percec, V. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 4756-4765 10.1002/pola.24922
55. Zhang, Q.; Wilson, P.; Li, Z.; McHale, R.; Godfrey, J.; Anastasaki, A.; Waldron, C.; Haddleton, D. M. J. Am. Chem. Soc. 2013, 135, 7355-7363 10.1021/ja4026402
56. Percec, V.; Guliashvili, T.; Ladislaw, J. S.; Wistrand, A.; Stjerndahl, A.; Sienkowska, M. J.; Monteiro, M. J.; Sahoo, S. J. Am. Chem. Soc. 2006, 128, 14156-14165 10.1021/ja065484z
57. Nguyen, N. H.; Rosen, B. M.; Lligadas, G.; Percec, V. Macromolecules 2009, 42, 2379-2386 10.1021/ma8028562
58. Mosnacek, J.; Eckstein-Andicsova, A.; Borska, K. Polym. Chem. 2015, 6, 2523-2530 10.1039/C4PY01807A
59. Mosnáček, J.; Kundys, A.; Andicsová, A. Polymers 2014, 6, 2862-2874 10.3390/polym6112862
60. Leibfarth, F. A.; Mattson, K. M.; Fors, B. P.; Collins, H. A.; Hawker, C. J. Angew. Chem., Int. Ed. 2013, 52, 199-210 10.1002/anie.201206476
61. Poelma, J. E.; Fors, B. P.; Meyers, G. F.; Kramer, J. W.; Hawker, C. J. Angew. Chem., Int. Ed. 2013, 52, 6844-6848 10.1002/anie.201301845
62. Yamago, S.; Ukai, Y.; Matsumoto, A.; Nakamura, Y. J. Am. Chem. Soc. 2009, 131, 2100-2101 10.1021/ja8099689
63. Xiao, P.; Zhang, J.; Dumur, F.; Tehfe, M. A.; Morlet-Savary, F.; Graff, B.; Gigmes, D.; Fouassier, J. P.; Lalevée, J. Prog. Polym. Sci. 2015, 41, 32-66 10.1016/j.progpolymsci.2014.09.001
64. Nakamura, Y.; Arima, T.; Tomita, S.; Yamago, S. J. Am. Chem. Soc. 2012, 134, 5536-5539 10.1021/ja300869x
65. Muthukrishnan, S.; Pan, E. H.; Stenzel, M. H.; Barner-Kowollik, C.; Davis, T. P.; Lewis, D.; Barner, L. Macromolecules 2007, 40, 2978-2980 10.1021/ma0703094
66. Liu, G.; Shi, H.; Cui, Y.; Tong, J.; Zhao, Y.; Wang, D.; Cai, Y. Polym. Chem. 2013, 4, 1176-1182 10.1039/C2PY20810E
67. Khan, M. Y.; Cho, M.-S.; Kwark, Y.-J. Macromolecules 2014, 47, 1929-1934 10.1021/ma5002244
68. Ohtsuki, A.; Goto, A.; Kaji, H. Macromolecules 2013, 46, 96-102 10.1021/ma302244j
69. Tasdelen, M. A.; Çifct, M.; Uygun, M.; Yagci, Y. In Progress in Controlled Radical Polymerization: Mechanisms and Techniques; American Chemical Society: Washington, D.C., 2012; Vol. 1100, pp 59-72.
70. Shi, Y.; Liu, G.; Gao, H.; Lu, L.; Cai, Y. Macromolecules 2009, 42, 3917-3926 10.1021/ma9000513
71. Zhang, H.; Deng, J.; Lu, L.; Cai, Y. Macromolecules 2007, 40, 9252-9261 10.1021/ma071287o
72. Bansal, A.; Kumar, A.; Kumar, P.; Bojja, S.; Chatterjee, A. K.; Ray, S. S.; Jain, S. L. RSC Adv. 2015, 5, 21189-21196 10.1039/C4RA15615C
73. Zhang, J.; Li, A.; Liu, H.; Yang, D.; Liu, J. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2715-2724 10.1002/pola.27288
74. Cao, Y.; Xu, Y.; Zhang, J.; Yang, D.; Liu, J. Polymer 2015, 61, 198-203 10.1016/j.polymer.2015.02.010
75. Kermagoret, A.; Wenn, B.; Debuigne, A.; Jerome, C.; Junkers, T.; Detrembleur, C. Polym. Chem. 2015, 6, 3847-3857 10.1039/C5PY00299K
76. Anastasaki, A.; Nikolaou, V.; Brandford-Adams, F.; Nurumbetov, G.; Zhang, Q.; Clarkson, G. J.; Fox, D. J.; Wilson, P.; Kempe, K.; Haddleton, D. M. Chem. Commun. 2015, 51, 5626-5629 10.1039/C4CC09916H
77. Zydziak, N.; Feist, F.; Huber, B.; Mueller, J. O.; Barner-Kowollik, C. Chem. Commun. 2015, 51, 1799-1802 10.1039/C4CC08756A
78. Karatsu, T.; Yanai, M.; Yagai, S.; Mizukami, J.; Urano, T.; Kitamura, A. J. Photochem. Photobiol., A 2005, 170, 123-129 10.1016/j.jphotochem.2004.08.010
79. Zhang, S.; Li, B.; Tang, L.; Wang, X.; Liu, D.; Zhou, Q. Polymer 2001, 42, 7575-7582 10.1016/S0032-3861(01)00233-6
80. Nagtegaele, P.; Galstian, T. V. Synth. Met. 2002, 127, 85-87 10.1016/S0379-6779(01)00601-4
81. Tehfe, M.-A.; Lalevée, J.; Morlet-Savary, F.; Graff, B.; Blanchard, N.; Fouassier, J.-P. Macromolecules 2012, 45, 1746-1752 10.1021/ma300050n
82. Lalevée, J.; Tehfe, M.-A.; Zein-Fakih, A.; Ball, B.; Telitel, S.; Morlet-Savary, F.; Graff, B.; Fouassier, J. P. ACS Macro Lett. 2012, 1, 802-806 10.1021/mz3002325
83. Xiao, P.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J. P.; Lalevée, J. Macromol. Rapid Commun. 2013, 34, 1452-1458 10.1002/marc.201300383
84. Xiao, P.; Frigoli, M.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J. P.; Lalevée, J. Macromolecules 2014, 47, 106-112 10.1021/ma402196p
85. Xiao, P.; Dumur, F.; Graff, B.; Fouassier, J. P.; Gigmes, D.; Lalevée, J. Macromolecules 2013, 46, 6744-6750 10.1021/ma401513b
86. Tehfe, M.-A.; Lalevée, J.; Morlet-Savary, F.; Graff, B.; Fouassier, J.-P. Macromolecules 2011, 44, 8374-8379 10.1021/ma2017265
87. Lu, L.; Zhang, H.; Yang, N.; Cai, Y. Macromolecules 2006, 39, 3770-3776 10.1021/ma060157x
88. Shinokubo, H.; Osuka, A. Chem. Commun. 2009, 1011-1021 10.1039/b817941g
89. Dolphin, D. In The Porphyrins; Dolphin, D., Ed.; Academic Press: Waltham, MA, 1978; p xv.
90. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40-48 10.1021/ar9801301
91. Collman, J.; Zhang, X.; Lee, V.; Uffelman, E.; Brauman, J. Science 1993, 261, 1404-1411 10.1126/science.8367724
92. Lin, V.; DiMagno, S.; Therien, M. Science 1994, 264, 1105-1111 10.1126/science.8178169
93. L. Anderson, H. Chem. Commun. 1999, 2323-2330 10.1039/a904209a
94. Holten, D.; Bocian, D. F.; Lindsey, J. S. Acc. Chem. Res. 2002, 35, 57-69 10.1021/ar970264z
95. Ethirajan, M.; Chen, Y.; Joshi, P.; Pandey, R. K. Chem. Soc. Rev. 2011, 40, 340-362 10.1039/B915149B
96. Sugimoto, H.; Kuroki, M.; Watanabe, T.; Kawamura, C.; Aida, T.; Inoue, S. Macromolecules 1993, 26, 3403-3410 10.1021/ma00065a025
97. Inoue, S.; Aida, T.; Watanabe, Y.; Kawaguchi, K.-I. Makromol. Chem., Macromol. Symp. 1991, 42-43, 365-371 10.1002/masy.19910420130
98. Inoue, S.; Sugimoto, H.; Aida, T. Macromol. Symp. 1996, 101, 11-18 10.1002/masy.19961010104
99. Simakova, A.; Mackenzie, M.; Averick, S. E.; Park, S.; Matyjaszewski, K. Angew. Chem., Int. Ed. 2013, 52, 12148-12151 10.1002/anie.201306337
100. Sigg, S. J.; Seidi, F.; Renggli, K.; Silva, T. B.; Kali, G.; Bruns, N. Macromol. Rapid Commun. 2011, 32, 1710-1715 10.1002/marc.201100349
101. Nguyen, K. A.; Day, P. N.; Pachter, R.; Tretiak, S.; Chernyak, V.; Mukamel, S. J. Phys. Chem. A 2002, 106, 10285-10293 10.1021/jp020053y
102. Harriman, A. J. Chem. Soc., Faraday Trans. 1 1980, 76, 1978-1985 10.1039/f19807601978
103. Harriman, A. J. Chem. Soc., Faraday Trans. 2 1981, 77, 1281-1291 10.1039/f29817701281
104. Harriman, A. J. Chem. Soc., Faraday Trans. 1 1981, 77, 369-377 10.1039/f19817700369
105. Fajer, J.; Borg, D. C.; Forman, A.; Dolphin, D.; Felton, R. H. J. Am. Chem. Soc. 1970, 92, 3451-3459 10.1021/ja00714a038
106. Pekkarinen, L.; Linschitz, H. J. Am. Chem. Soc. 1960, 82, 2407-2411 10.1021/ja01495a001
107. Seely, G. R. Photochem. Photobiol. 1978, 27, 639-654 10.1111/j.1751-1097.1978.tb07658.x
108. Dreas-Wlodarczak, A.; Müllneritsch, M.; Juffmann, T.; Cioffi, C.; Arndt, M.; Mayor, M. Langmuir 2010, 26, 10822-10826 10.1021/la100638u
109. Uchiyama, M.; Satoh, K.; Kamigaito, M. Angew. Chem., Int. Ed. 2015, 54, 1924-1928 10.1002/anie.201410858
110. Kumagai, S.; Nagai, K.; Satoh, K.; Kamigaito, M. Macromolecules 2010, 43, 7523-7531 10.1021/ma101420u
111. Aoshima, H.; Uchiyama, M.; Satoh, K.; Kamigaito, M. Angew. Chem., Int. Ed. 2014, 53, 10932-10936 10.1002/anie.201406590
112. Xu, J.; Shanmugam, S.; Corrigan, N. A.; Boyer, C. In Controlled Radical Polymerization: Mechanisms; American Chemical Society: Washington, D.C., 2015; Vol. 1187, pp 247-267.
113. Konishi, T.; Ikeda, A.; Asai, M.; Hatano, T.; Shinkai, S.; Fujitsuka, M.; Ito, O.; Tsuchiya, Y.; Kikuchi, J.-I. J. Phys. Chem. B 2003, 107, 11261-11266 10.1021/jp0273878
114. Goto, A.; Fukuda, T. Prog. Polym. Sci. 2004, 29, 329-385 10.1016/j.progpolymsci.2004.01.002
115. Nappa, M.; Valentine, J. S. J. Am. Chem. Soc. 1978, 100, 5075-5080 10.1021/ja00484a027
116. Teodorescu, M.; Matyjaszewski, K. Macromolecules 1999, 32, 4826-4831 10.1021/ma990175x
117. Teodorescu, M.; Matyjaszewski, K. Macromol. Rapid Commun. 2000, 21, 190-194 10.1002/(SICI)1521-3927(200003)21:4<190::AID-MARC190>3.0.CO;2-S
118. Nguyen, N. H.; Rodriguez-Emmenegger, C.; Brynda, E.; Sedlakova, Z.; Percec, V. Polym. Chem. 2013, 4, 2424-2427 10.1039/c3py00220a
119. Senoo, M.; Kotani, Y.; Kamigaito, M.; Sawamoto, M. Macromolecules 1999, 32, 8005-8009 10.1021/ma9909814
120. Min, K.; Jakubowski, W.; Matyjaszewski, K. Macromol. Rapid Commun. 2006, 27, 594-598 10.1002/marc.200600060
121. McMahon, J. J.; Barry, M.; Breen, K. J.; Radziwon, A. K.; Brooks, L. D.; Blair, M. R. J. Phys. Chem. C 2008, 112, 1158-1166 10.1021/jp075143n
122. Wang, G.; Lu, M.; Wu, H. Polym. Bull. 2012, 69, 417-427 10.1007/s00289-012-0735-9
123. Gody, G.; Barbey, R.; Danial, M.; Perrier, S. Polym. Chem. 2015, 6, 1502-1511 10.1039/C4PY01251H
124. Rosenblum, W. I.; El-Sabban, F. Stroke 1982, 13, 35-39 10.1161/01.STR.13.1.35
125. Valko, M.; Izakovic, M.; Mazur, M.; Rhodes, C. J.; Telser, J. Mol. Cell. Biochem. 2004, 266, 37-56 10.1023/B:MCBI.0000049134.69131.89
126. Kadish, K. M.; Davis, D. G. Ann. N. Y. Acad. Sci. 1973, 206, 495-503 10.1111/j.1749-6632.1973.tb43232.x