Mechanism of Photoinduced Metal-Free Atom Transfer Radical Polymerization: Experimental and Computational Studies

Journal of the American Chemical Society

Volumn 138, Issue 7, 2016, Pages 2411-2425

  Pan, Xiangcheng ^a   Fang, Cheng ^b   Fantin, Marco ^a,c   Malhotra, Nikhil ^a   So, Woong Young ^a   Peteanu, Linda A ^a   Isse, Abdirisak A ^c   Gennaro, Armando ^c   Liu, Peng ^b   Matyjaszewski, Krzysztof ^a  

^a CARNEGIE MELLON UNIVERSITY   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

^c UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC MONOMERS; ACTIVATION ANALYSIS; CATALYST ACTIVITY; CATALYST DEACTIVATION; CATALYSTS; CHEMICAL ACTIVATION; COMPUTATION THEORY; CYCLIC VOLTAMMETRY; DENSITY FUNCTIONAL THEORY; DESIGN FOR TESTABILITY; ELECTRON TRANSITIONS; ESTERS; EXCITED STATES; FREE RADICAL POLYMERIZATION; FREE RADICAL REACTIONS; PHOTODISSOCIATION; PHOTOLYSIS; POLYMERIZATION; POSITIVE IONS; REACTION INTERMEDIATES;

ACTIVATION PROCESS; COMPUTATIONAL STUDIES; DEACTIVATION PATHWAYS; DEACTIVATION PROCESS; DISSOCIATIVE ELECTRON TRANSFERS; LASER FLASH PHOTOLYSIS; METHYL METHACRYLATES; PHENOTHIAZINE DERIVATIVES;

ATOM TRANSFER RADICAL POLYMERIZATION;

CATION; CUPROUS ION; METHACRYLIC ACID METHYL ESTER; PHENOTHIAZINE DERIVATIVE;

ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; CATALYST; CHEMICAL REACTION; CYCLIC POTENTIOMETRY; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; KINETICS; LASER FLASH PHOTOLYSIS; MOLECULAR WEIGHT; PHOTOLYSIS; POLYMERIZATION; QUANTUM YIELD; RATE CONSTANT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

EID: 84959423222     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b13455     Document Type: Article

References (114)

1. Goto, A.; Fukuda, T. Prog. Polym. Sci. 2004, 29, 329-385 10.1016/j.progpolymsci.2004.01.002
2. Braunecker, W. A.; Matyjaszewski, K. Prog. Polym. Sci. 2007, 32, 93-146 10.1016/j.progpolymsci.2006.11.002
3. Matyjaszewski, K.; Davis, T. P. Handbook of radical polymerization; Wiley and Sons, Inc.: Hoboken, NJ, 2002.
4. Nicolas, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B. Prog. Polym. Sci. 2013, 38, 63-235 10.1016/j.progpolymsci.2012.06.002
5. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688 10.1021/cr990119u
6. Wang, J.-S.; Matyjaszewski, K. J. Am. Chem. Soc. 1995, 117, 5614-5615 10.1021/ja00125a035
7. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Macromolecules 1995, 28, 1721-1723 10.1021/ma00109a056
8. Patten, T. E.; Xia, J.; Abernathy, T.; Matyjaszewski, K. Science 1996, 272, 866-868 10.1126/science.272.5263.866
9. Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990 10.1021/cr940534g
10. Matyjaszewski, K.; Tsarevsky, N. V. J. Am. Chem. Soc. 2014, 136, 6513-6533 10.1021/ja408069v
11. Matyjaszewski, K. Macromolecules 2012, 45, 4015-4039 10.1021/ma3001719
12. Chiefari, J.; Chong, Y. K.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T. P. T.; Mayadunne, R. T. A.; Meijs, G. F.; Moad, C. L.; Moad, G.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559-5562 10.1021/ma9804951
13. Hill, M. R.; Carmean, R. N.; Sumerlin, B. S. Macromolecules 2015, 48, 5459-5469 10.1021/acs.macromol.5b00342
14. De Paoli, P.; Isse, A. A.; Bortolamei, N.; Gennaro, A. Chem. Commun. 2011, 47, 3580-3582 10.1039/c1cc10195a
15. Matyjaszewski, K.; Patten, T. E.; Xia, J. J. Am. Chem. Soc. 1997, 119, 674-680 10.1021/ja963361g
16. Pintauer, T.; Matyjaszewski, K. Chem. Soc. Rev. 2008, 37, 1087-1097 10.1039/b714578k
17. Jakubowski, W.; Matyjaszewski, K. Angew. Chem., Int. Ed. 2006, 45, 4482-4486 10.1002/anie.200600272
18. Matyjaszewski, K.; Jakubowski, W.; Min, K.; Tang, W.; Huang, J.; Braunecker, W. A.; Tsarevsky, N. V. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 15309-15314 10.1073/pnas.0602675103
19. Konkolewicz, D.; Wang, Y.; Krys, P.; Zhong, M.; Isse, A. A.; Gennaro, A.; Matyjaszewski, K. Polym. Chem. 2014, 5, 4396-4417 10.1039/c4py00149d
20. Konkolewicz, D.; Wang, Y.; Zhong, M.; Krys, P.; Isse, A. A.; Gennaro, A.; Matyjaszewski, K. Macromolecules 2013, 46, 8749-8772 10.1021/ma401243k
21. Rosen, B. M.; Percec, V. Chem. Rev. 2009, 109, 5069-5119 10.1021/cr900024j
22. Magenau, A. J. D.; Strandwitz, N. C.; Gennaro, A.; Matyjaszewski, K. Science 2011, 332, 81-84 10.1126/science.1202357
23. Park, S.; Chmielarz, P.; Gennaro, A.; Matyjaszewski, K. Angew. Chem., Int. Ed. 2015, 54, 2388-2392 10.1002/anie.201410598
24. Bortolamei, N.; Isse, A. A.; Magenau, A. J. D.; Gennaro, A.; Matyjaszewski, K. Angew. Chem., Int. Ed. 2011, 50, 11391-11394 10.1002/anie.201105317
25. Konkolewicz, D.; Schroder, K.; Buback, J.; Bernhard, S.; Matyjaszewski, K. ACS Macro Lett. 2012, 1, 1219-1223 10.1021/mz300457e
26. Ribelli, T. G.; Konkolewicz, D.; Pan, X.; Matyjaszewski, K. Macromolecules 2014, 47, 6316-6321 10.1021/ma501384q
27. Mosnáček, J.; Ilčíková, M. Macromolecules 2012, 45, 5859-5865 10.1021/ma300773t
28. 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
29. Pan, X.; Malhotra, N.; Simakova, A.; Wang, Z.; Konkolewicz, D.; Matyjaszewski, K. J. Am. Chem. Soc. 2015, 137, 15430-15433 10.1021/jacs.5b11599
30. Dadashi-Silab, S.; Tasdelen, M. A.; Yagci, Y. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2878-2888 10.1002/pola.27327
31. Ciftci, M.; Tasdelen, M. A.; Li, W.; Matyjaszewski, K.; Yagci, Y. Macromolecules 2013, 46, 9537-9543 10.1021/ma402058a
32. Tasdelen, M. A.; Ciftci, M.; Yagci, Y. Macromol. Chem. Phys. 2012, 213, 1391-1396 10.1002/macp.201200204
33. Tasdelen, M. A.; Uygun, M.; Yagci, Y. Macromol. Rapid Commun. 2011, 32, 58-62 10.1002/marc.201000351
34. Tasdelen, M. A.; Uygun, M.; Yagci, Y. Macromol. Chem. Phys. 2010, 211, 2271-2275 10.1002/macp.201000445
35. Kwak, Y.; Matyjaszewski, K. Macromolecules 2010, 43, 5180-5183 10.1021/ma100850a
36. Pan, X.; Malhotra, N.; Zhang, J.; Matyjaszewski, K. Macromolecules 2015, 48, 6948-6954 10.1021/acs.macromol.5b01815
37. Yang, Q.; Dumur, F.; Morlet-Savary, F.; Poly, J.; Lalevée, J. Macromolecules 2015, 48, 1972-1980 10.1021/ma502384y
38. Fors, B. P.; Hawker, C. J. Angew. Chem., Int. Ed. 2012, 51, 8850-8853 10.1002/anie.201203639
39. Meyer, T. J. Acc. Chem. Res. 1989, 22, 163-170 10.1021/ar00161a001
40. Lalrempuia, R.; McDaniel, N. D.; Müller-Bunz, H.; Bernhard, S.; Albrecht, M. Angew. Chem., Int. Ed. 2010, 49, 9765-9768 10.1002/anie.201005260
41. DiSalle, B. F.; Bernhard, S. J. Am. Chem. Soc. 2011, 133, 11819-11821 10.1021/ja201514e
42. Kalyanasundaram, K. Coord. Chem. Rev. 1982, 46, 159-244 10.1016/0010-8545(82)85003-0
43. Howerton, B. S.; Heidary, D. K.; Glazer, E. C. J. Am. Chem. Soc. 2012, 134, 8324-8327 10.1021/ja3009677
44. Kärkäs, M. D.; Matsuura, B. S.; Stephenson, C. R. J. Science 2015, 349, 1285-1286 10.1126/science.aad0193
45. Le, C. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 11938-11941 10.1021/jacs.5b08304
46. Nawrat, C. C.; Jamison, C. R.; Slutskyy, Y.; MacMillan, D. W. C.; Overman, L. E. J. Am. Chem. Soc. 2015, 137, 11270-11273 10.1021/jacs.5b07678
47. Jin, J.; MacMillan, D. W. C. Nature 2015, 525, 87-90 10.1038/nature14885
48. Terrett, J. A.; Cuthbertson, J. D.; Shurtleff, V. W.; MacMillan, D. W. C. Nature 2015, 524, 330-334 10.1038/nature14875
49. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363 10.1021/cr300503r
50. Romero, N. A.; Margrey, K. A.; Tay, N. E.; Nicewicz, D. A. Science 2015, 349, 1326-1330 10.1126/science.aac9895
51. Griffin, J. D.; Zeller, M. A.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 11340-11348 10.1021/jacs.5b07770
52. Lalevée, J.; Peter, M.; Dumur, F.; Gigmes, D.; Blanchard, N.; Tehfe, M.-A.; Morlet-Savary, F.; Fouassier, J. P. Chem.-Eur. J. 2011, 17, 15027-15031 10.1002/chem.201101445
53. Lalevée, J.; Blanchard, N.; Tehfe, M.-A.; Morlet-Savary, F.; Fouassier, J. P. Macromolecules 2010, 43, 10191-10195 10.1021/ma1023318
54. Ogawa, K. A.; Goetz, A. E.; Boydston, A. J. J. Am. Chem. Soc. 2015, 137, 1400-1403 10.1021/ja512073m
55. 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
56. Perkowski, A. J.; You, W.; Nicewicz, D. A. J. Am. Chem. Soc. 2015, 137, 7580-7583 10.1021/jacs.5b03733
57. Xu, J.; Jung, K.; Atme, A.; Shanmugam, S.; Boyer, C. J. Am. Chem. Soc. 2014, 136, 5508-5519 10.1021/ja501745g
58. Shanmugam, S.; Xu, J.; Boyer, C. J. Am. Chem. Soc. 2015, 137, 9174-9185 10.1021/jacs.5b05274
59. Shanmugam, S.; Xu, J.; Boyer, C. Chem. Sci. 2015, 6, 1341-1349 10.1039/C4SC03342F
60. Xu, J.; Shanmugam, S.; Duong, H. T.; Boyer, C. Polym. Chem. 2015, 6, 5615-5624 10.1039/C4PY01317D
61. Shanmugam, S.; Boyer, C. J. Am. Chem. Soc. 2015, 137, 9988-9999 10.1021/jacs.5b05903
62. Yeow, J.; Xu, J.; Boyer, C. ACS Macro Lett. 2015, 4, 984-990 10.1021/acsmacrolett.5b00523
63. Chen, M.; MacLeod, M. J.; Johnson, J. A. ACS Macro Lett. 2015, 4, 566-569 10.1021/acsmacrolett.5b00241
64. 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
65. 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
66. 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
67. Pan, X.; Lamson, M.; Yan, J.; Matyjaszewski, K. ACS Macro Lett. 2015, 4, 192-196 10.1021/mz500834g
68. Kaur, A.; Ribelli, T. G.; Schröder, K.; Matyjaszewski, K.; Pintauer, T. Inorg. Chem. 2015, 54, 1474-1486 10.1021/ic502484s
69. Lin, C. Y.; Coote, M. L.; Gennaro, A.; Matyjaszewski, K. J. Am. Chem. Soc. 2008, 130, 12762-12774 10.1021/ja8038823
70. Isse, A. A.; Bortolamei, N.; De Paoli, P.; Gennaro, A. Electrochim. Acta 2013, 110, 655-662 10.1016/j.electacta.2013.04.132
71. Marcus, R. A. J. Chem. Phys. 1956, 24, 966-978 10.1063/1.1742723
72. Pause, L.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2000, 122, 9829-9835 10.1021/ja001258s
73. Saveant, J. M. J. Am. Chem. Soc. 1987, 109, 6788-6795 10.1021/ja00256a037
74. Saveant, J. M. J. Am. Chem. Soc. 1992, 114, 10595-10602 10.1021/ja00052a065
75. Isse, A. A.; Gennaro, A.; Lin, C. Y.; Hodgson, J. L.; Coote, M. L.; Guliashvili, T. J. Am. Chem. Soc. 2011, 133, 6254-6264 10.1021/ja110538b
76. Flamigni, L.; Barbieri, A.; Sabatini, C.; Ventura, B.; Barigelletti, F. In Photochemistry and Photophysics of Coordination Compounds II; Balzani, V.; Campagna, S., Eds.; Springer: Berlin Heidelberg, 2007; Topics in Current Chemistry, Vol. 281.
77. Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875-8884 10.1021/ja300798k
78. Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160-4163 10.1021/ja108560e
79. Lin, C. Y.; Coote, M. L.; Petit, A.; Richard, P.; Poli, R.; Matyjaszewski, K. Macromolecules 2007, 40, 5985-5994 10.1021/ma070911u
80. Nanda, A. K.; Matyjaszewski, K. Macromolecules 2003, 36, 8222-8224 10.1021/ma035219n
81. Pérez-Prieto, J.; Miranda, M. A. In Encyclopedia of Radicals in Chemistry, Biology and Materials; John Wiley & Sons, Ltd: Hoboken, NJ, 2012.
82. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27-50 10.1039/C0SC00331J
83. Crivello, J. V. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3820-3829 10.1002/pola.22731
84. Tehfe, M.-A.; Lalevée, J.; Morlet-Savary, F.; Graff, B.; Blanchard, N.; Fouassier, J.-P. ACS Macro Lett. 2012, 1, 198-203 10.1021/mz200140y
85. Kolosov, D.; Adamovich, V.; Djurovich, P.; Thompson, M. E.; Adachi, C. J. Am. Chem. Soc. 2002, 124, 9945-9954 10.1021/ja0263588
86. Lifetime of Ph-PTZ∗ is 2.3 ns, measured in MeCN, see: Discekici, E. H.; Treat, N. J.; Poelma, S. O.; Mattson, K. M.; Hudson, Z. M.; Luo, Y.; Hawker, C. J.; de Alaniz, J. R. Chem. Commun. 2015, 51, 11705 10.1039/C5CC04677G
87. Isse, A. A.; Sandonà, G.; Durante, C.; Gennaro, A. Electrochim. Acta 2009, 54, 3235-3243 10.1016/j.electacta.2008.12.034
88. Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2003, 125, 10729-10739 10.1021/ja036141t
89. Isse, A. A.; Gennaro, A. J. Phys. Chem. A 2004, 108, 4180-4186 10.1021/jp036782a
90. Cardinale, A.; Isse, A. A.; Gennaro, A.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2002, 124, 13533-13539 10.1021/ja0275212
91. Andrieux, C. P.; Le Gorande, A.; Saveant, J. M. J. Am. Chem. Soc. 1992, 114, 6892-6904 10.1021/ja00043a039
92. Andrieux, C. P.; Gallardo, I.; Savaent, J. M.; Su, K. B. J. Am. Chem. Soc. 1986, 108, 638-647 10.1021/ja00264a013
93. Pause, L.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2001, 123, 4886-4895 10.1021/ja004234u
94. Isse, A. A.; Lin, C. Y.; Coote, M. L.; Gennaro, A. J. Phys. Chem. B 2011, 115, 678-684 10.1021/jp109613t
95. Saucin, M.; Van de Vorst, A. Radiat. Environ. Biophys. 1980, 17, 159-168 10.1007/BF02027852
96. Jung, S. O.; Kim, Y.-H.; Kim, H.-S.; Kwon, S.-K.; Oh, H.-Y. Mol. Cryst. Liq. Cryst. 2006, 444, 95-101 10.1080/15421400500365243
97. Rehm, D.; Weller, A. Isr. J. Chem. 1970, 8, 259-271 10.1002/ijch.197000029
98. Konkolewicz, D.; Krys, P.; Góis, J. R.; Mendonça, P. V.; Zhong, M.; Wang, Y.; Gennaro, A.; Isse, A. A.; Fantin, M.; Matyjaszewski, K. Macromolecules 2014, 47, 560-570 10.1021/ma4022983
99. Lorandi, F.; Fantin, M.; Isse, A. A.; Gennaro, A. Polymer 2015, 72, 238-245 10.1016/j.polymer.2015.04.007
100. Fantin, M.; Isse, A. A.; Gennaro, A.; Matyjaszewski, K. Macromolecules 2015, 48, 6862-6875 10.1021/acs.macromol.5b01454
101. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Herndon, VA, 1978.
102. Bortolamei, N.; Isse, A. A.; Gennaro, A. Electrochim. Acta 2010, 55, 8312-8318 10.1016/j.electacta.2010.02.099
103. Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C. J. Am. Chem. Soc. 2015, 137, 4896-4899 10.1021/ja513079r
104. Demissie, T. B.; Ruud, K.; Hansen, J. H. Organometallics 2015, 34, 4218-4228 10.1021/acs.organomet.5b00582
105. Pan, D.; Phillips, D. L. J. Phys. Chem. A 1999, 103, 4737-4743 10.1021/jp990399h
106. Okamoto, T.; Kuratsu, M.; Kozaki, M.; Hirotsu, K.; Ichimura, A.; Matsushita, T.; Okada, K. Org. Lett. 2004, 6, 3493-3496 10.1021/ol048698z
107. Savéant, J.-M. J. Electroanal. Chem. 2000, 485, 86-88 10.1016/S0022-0728(00)00078-4
108. Shine, H. J.; Silber, J. J.; Bussey, R. J.; Okuyama, T. J. Org. Chem. 1972, 37, 2691-2697 10.1021/jo00982a014
109. Tolman, R. C. Statistical Mechanics; Chemical Catalog Co.: New York, 1927; p 247.
110. Partington, J. R. An Advanced Treatise on Physical Chemistry; Longmans: London, 1967; Vol. 1, p 292.
111. Moore, J.W.; Pearson, R. N. Kinetics and Mechanism; Wiley: New York, 1981; Vol. 131, p 130.
112. Matyjaszewski, K.; Paik, H.-j.; Zhou, P.; Diamanti, S. J. Macromolecules 2001, 34, 5125-5131 10.1021/ma010185+
113. Tang, W.; Kwak, Y.; Braunecker, W.; Tsarevsky, N. V.; Coote, M. L.; Matyjaszewski, K. J. Am. Chem. Soc. 2008, 130, 10702-10713 10.1021/ja802290a
114. Zerk, T. J.; Bernhardt, P. V. Inorg. Chem. 2014, 53, 11351-11353 10.1021/ic5022005