Perylene as an organic photocatalyst for the radical polymerization of functionalized vinyl monomers through oxidative quenching with alkyl bromides and visible light

Macromolecules

Volumn 47, Issue 23, 2014, Pages 8255-8261

  Miyake, Garret M ^a,b   Theriot, Jordan C ^a  

^a UNIVERSITY OF COLORADO   (United States)

^b California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC MONOMERS; ATOM TRANSFER RADICAL POLYMERIZATION; BLOCK COPOLYMERS; CARBON; ESTERS; LIGHT; MONOMERS; NATURAL POLYMERS; POLYCYCLIC AROMATIC HYDROCARBONS; POLYMERIZATION; QUENCHING;

ALKYL BROMIDES; CARBON-CARBON BOND FORMATION; CARBON-CENTERED RADICALS; FUNCTIONALIZED; NATURAL SUNLIGHT; POLYMERIZATION OF METHYL METHACRYLATE; VINYL MONOMERS; VISIBLE-LIGHT PHOTOCATALYSTS;

POLYMERS;

EID: 84916620212     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma502044f     Document Type: Article

References (64)

1. Fouassier, J.-F.; Lalevée, J. Photoinitiators for Polymer Synthesis; Wiley-VCH: Weinheim, Germany, 2012.
2. Yagci, Y.; Jockusch, S.; Turro, N. J. Macromolecules 2010, 43, 6245-6260
3. Chatani, S.; Kloxin, C. J.; Bowman, C. N. Polym. Chem. 2014, 5, 2187-2201
4. Monroe, B. M.; Weed, G. C. Chem. Rev. 1993, 93, 435-448
5. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176
6. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363
7. Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355-360
8. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102-113
9. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527-532
10. Albini, A.; Fagnoni, M. ChemSusChem 2008, 1, 63-66
11. Fagnoni, M.; Dondi, D.; Ravelli, D.; Albini, A. Chem. Rev. 2007, 107, 2725-2756
12. Xu, J.; Jung, K.; Atme, A.; Shanmugam, S.; Boyer, C. J. Am. Chem. Soc. 2014, 136, 5508-5519
13. Weitekamp, R. A.; Atwater, H. A.; Grubbs, R. H. J. Am. Chem. Soc. 2013, 135, 16817-16820
14. Yamago, S.; Nakamura, Y. Polymer 2013, 54, 981-994
15. Ohtsuki, A.; Goto, A.; Kaji, H. Macromolecules 2013, 46, 96-102
16. Yamago, S.; Nakamura, Y. Polymer 2013, 54, 981-994
17. Yamago, S.; Ukai, Y.; Matsumoto, A.; Nakamura, Y. J. Am. Chem. Soc. 2009, 131, 2100-2101
18. Koumura, K.; Satoh, K.; Kamigaito, M. Macromolecules 2008, 41, 7359-7367
19. Matyjaszewski, K.; Tsarevsky, N. V. J. Am. Chem. Soc. 2014, 136, 6513-6533
20. Matyjaszewski, K. Macromolecules 2012, 45, 4015
21. di Lena, F.; Matyjaszewski, K. Prog. Polym. Sci. 2010, 35, 959-1021
22. Ouchi, M.; Terashima, T.; Sawamoto, M. Chem. Rev. 2009, 109, 4963-5050
23. Matyjaszewski, K.; Tsarevsky, N. V. Nat. Chem. 2009, 1, 276-288
24. Ouchi, M.; Terashima, T.; Sawamoto, M. Acc. Chem. Res. 2008, 41, 1120-1132
25. Braunecker, W. A.; Matyjaszewski, K. Prog. Polym. Sci. 2007, 32, 93-146
26. Matyjaszewski, K.; Xia, J. Chem. Rev. 2001, 101, 2921-2990
27. Ribelli, T. G.; Konkolewicz, D.; Bernhard, S.; Matyjaszewski, K. J. Am. Chem. Soc. 2014, 136, 13303-13312
28. Anastasaki, A.; Nikolaou, V.; Zhang, Z.; 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
29. Konkolewicz, D.; Schröder, K.; Buback, J.; Bernhard, S.; Matyjaszewski, K. ACS Macro Lett. 2012, 1, 1219-1223
30. Mosnáček, J.; Ilčiková, M. Macromolecules 2012, 45, 5859-5865
31. Tasdelen, M. A.; Uygun, M.; Yagci, Y. Macromol. Rapid Commun. 2011, 32, 58-62
32. Zhang, G.; Song, I. Y.; Ahn, K. H.; Park, T.; Choi, W. Macromolecules 2011, 44, 7594-7599
33. Treat, N. J.; Fors, B. P.; Kramer, J. W.; Christianson, M.; Chiu, C.-Y.; de Alaniz, J. R.; Hawker, C. J. ACS Macro Lett. 2014, 3, 580-584
34. Fors, B. P.; Hawker, C. J. Angew. Chem., Int. Ed. 2012, 51, 8850-8853
35. Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875-8884
36. Nguyen, J. D.; Tucker, J. W.; Konieczynska, M. D.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160-4163
37. Furst, L.; Matsuura, B. S.; Narayanam, J. M. R.; Tucker, J. W.; Stephenson, C. R. J. Org. Lett. 2010, 12, 3104-3107
38. Ravelli, D.; Fagnoni, M.; Albini, A. Chem. Soc. Rev. 2013, 42, 97-113
39. Fukuzumi, S.; Ohkubo, K. Chem. Sci. 2013, 4, 561-574
40. Ravelli, D.; Fagnoni, M. ChemCatChem 2012, 4, 169-171
41. Lalevée, J.; Telitel, S.; Xiao, P.; Lepeltier, M.; Dumur, F.; Morlet-Savary, F.; Gigmes, D.; Fouassier, J.-P. Belstein J. Org. Chem. 2014, 10, 863-876
42. Lalevée, J.; Tehfe, M.-A.; Morlet-Savary, F.; Graff, B.; Dumar, F.; Gigmes, D.; Blanchard, N.; Fouassier, J.-P. Chimia 2012, 55, 439-441
43. Fouassier, J. P.; Allonas, X.; Burget, D. Prog. Org. Coat. 2003, 47, 16-36
44. Broggi, J.; Terme, T.; Vanelle, P. Angew. Chem., Int. Ed. 2014, 53, 384-413
45. Tehfe, M.-A.; Dumur, F.; Contal, E.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Macromol. Chem. Phys. 2013, 214, 2189-2201
46. Nicola, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B. Prog. Polym. Sci. 2013, 38, 63-235
47. Hawker, C. J.; Bosman, A. W.; Harth, E. Chem. Rev. 2001, 101, 3661-3688
48. Moad, G.; Rizzardo, E.; Thang, S. H. Aust. J. Chem. 2009, 62, 1402-1472
49. Moad, G.; Rizzardo, E.; Thang, S. H. Polymer 2008, 49, 1078-1131
50. Moad, G.; Rizzardo, E.; Thang, S. H. Aust. J. Chem. 2006, 59, 669-692
51. Moad, G.; Rizzardo, E.; Thang, S. H. Aust. J. Chem. 2005, 58, 379-410
52. Moad, G.; Rizzardo, E.; Thang, S. H. Acc. Chem. Res. 2008, 41, 1133-1142
53. Tanishima, M.; Goto, A.; Lei, L.; Ohtsuki, A.; Kaji, H.; Nomura, A.; Tsujii, Y.; Yamaguchi, Y.; Komatsu, H.; Miyamoto, M. Polymers 2014, 6, 311-326
54. Goto, A.; Ohtsuki, A.; Ohfuji, H.; Tanishima, M.; Kaji, H. J. Am. Chem. Soc. 2013, 135, 11131-11139
55. Goto, A.; Suzuki, T.; Ohfuji, H.; Tanishima, M.; Fukuda, T.; Tsujii, Y.; Kaji, H. Macromolecules 2011, 44, 8709-8715
56. Goto, A.; Wakada, T.; Fukuda, T.; Tsujii, Y. Macromol. Chem. Phys. 2010, 211, 594-600
57. Goto, A.; Tsujii, T.; Fukuda, T. Polymer 2008, 49, 5177-5185
58. Li, C.; Wonneberger, H. Adv. Mater. 2012, 24, 613-636
59. Weil, T.; Vosch, T.; Hofkens, J.; Peneva, K.; Müllen, K. Angew. Chem., Int. Ed. 2010, 49, 9068-9093
60. Würthner, F. Chem. Commun. 2004, 1564-1579
61. Xiao, P.; Dumur, F.; Frigoli, M.; Graff, B.; Morlet-Savary, F.; Wantz, G.; Bock, H.; Fouassier, J. P.; Gigmes, D.; Lalevée Eur. Polym. J. 2014, 53, 215-222
62. Xia, P.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J. P.; Lalevée, J. Macromol. Rapid Commun. 2013, 34, 1452-1458
63. Tehfe, M.-A.; Dumur, F.; Graff, B.; Gigmes, D.; Fouassier, J.-P.; Lalevée, J. Macromol. Chem. Phys. 2013, 214, 1052-1060
64. Barner-Kowollik, C.; Davis, T. P.; Stenzel, M. H. Polymer 2004, 45, 7791-7805