Abstract
Iron and copper complexes with anionic phenolate-bis(pyridyl)amine ligands were synthesized and examined as catalysts for atom transfer radical polymerization (ATRP) of methyl (meth)acrylate and styrene. With copper complexes, polymers with narrow molecular weight distributions, M w /M n ~1.2, were prepared. The catalytic performance of copper catalysts was affected by nature of halogen species and by the steric and electronic effects. In iron-mediated ATRP procedures, the number-average molecular weights of the polymers increased with monomer conversion, however, the molecular weight distributions of the resulting polymers were relatively broad M w /M n ~1.7, due to slow deactivation processes.
Similar content being viewed by others
References
K. Matyjaszewski, S. Gaynor, D. Greszta, D. Mardare, and T. Shigemoto, J. Phys. Org. Chem., 8, 306 (1995).
K. Matyjaszewski, J. Phys. Org. Chem., 8, 197 (1995).
N. V. Tsarevsky and K. Matyjaszewski, Chem. Rev., 107, 2270 (2007).
K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001).
K. Matyjaszewski, Controlled Radical Polymerization: State-of-the-Art in 2014, American Chemical Society, Washington DC, 2015.
K. Matyjaszewski, Macromolecules, 45, 4015 (2012).
K. Matyjaszewski and N. V. Tsarevsky, J. Am. Chem. Soc., 136, 6513 (2014).
F. di Lena and K. Matyjaszewski, Prog. Polym. Sci., 35, 959 (2010).
M. Ouchi, T. Terashima, and M. Sawamoto, Chem. Rev., 109, 4963 (2009).
Z. Xue, D. He, and X. Xie, Polym. Chem., 6, 1660 (2015).
W. A. Braunecker, Y. Itami, and K. Matyjaszewski, Macromolecules, 38, 9402 (2005).
R. Poli, L. E. N. Allan, and M. P. Shaver, Prog. Polym. Sci., 39, 1827 (2014).
P. Krys and K. Matyjaszewski, Eur. Polym. J., 89, 482 (2017).
J. Qiu, B. Charleux, and K. Matyjaszewski, Prog. Polym. Sci., 26, 2083 (2001).
X. Pan, M. A. Tasdelen, J. Laun, T. Junkers, Y. Yagci, and K. Matyjaszewski, Prog. Polym. Sci., 62, 73 (2016).
J. K. Oh, R. Drumright, D. J. Siegwart, and K. Matyjaszewski, Prog. Polym. Sci., 33, 448 (2008).
K. Matyjaszewski, Prog. Polym. Sci., 30, 858 (2005).
V. Coessens, T. Pintauer, and K. Matyjaszewski, Prog. Polym. Sci., 26, 337 (2001).
D. J. Siegwart, J. K. Oh, and K. Matyjaszewski, Prog. Polym. Sci., 37, 18 (2012).
S. S. Sheiko, B. S. Sumerlin, and K. Matyjaszewski, Prog. Polym. Sci., 33, 759 (2008).
H.-I. Lee, J. Pietrasik, S. S. Sheiko, and K. Matyjaszewski, Prog. Polym. Sci., 35, 24 (2010).
H. Gao and K. Matyjaszewski, Prog. Polym. Sci., 34, 317 (2009).
K. Matyjaszewski, Science, 333, 1104 (2011).
J. Qiu and K. Matyjaszewski, Macromolecules, 30, 5643 (1997).
H. Shinoda and K. Matyjaszewski, Macromolecules, 34, 6243 (2001).
K. A. Davis, B. Charleux, and K. Matyjaszewski, J. Polym. Sci., Part A: Polym. Chem., 38, 2274 (2000).
K. Matyjaszewski, D. A. Shipp, G. P. McMurtry, S. G. Gaynor, and T. Pakula, J. Polym. Sci., Part A: Polym. Chem., 38, 2023 (2000).
X. Zhang and K. Matyjaszewski, Macromolecules, 32, 1763 (1999).
H. Shinoda, P. J. Miller, and K. Matyjaszewski, Macromolecules, 34, 3186 (2001).
J. Pyun, K. Matyjaszewski, T. Kowalewski, D. Savin, G. Patterson, G. Kickelbick, and N. Huesing, J. Am. Chem. Soc., 123, 9445 (2001).
B. S. Sumerlin, D. Neugebauer, and K. Matyjaszewski, Macromolecules, 38, 702 (2005).
S. V. Arehart and K. Matyjaszewski, Macromolecules, 32, 2221 (1999).
K. Matyjaszewski, Y. Nakagawa, and S.G. Gaynor, Macromol. Rapid Commun., 18, 1057 (1997).
S. H. Qin, K. Matyjaszewski, H. Xu, and S. S. Sheiko, Macromolecules, 36, 605 (2003).
X. K. D. Hillewaere and F. E. Du Prez, Prog. Polym. Sci., 49-50, 121 (2015).
T. N. Hoheisel, K. Hur, and U. B. Wiesner, Prog. Polym. Sci., 40, 3 (2015).
E. Mastan, X. Li, and S. Zhu, Prog. Polym. Sci., 45, 71 (2015).
B. Sarkar and P. Alexandridis, Prog. Polym. Sci., 40, 33 (2015).
M. W. Urban, Prog. Polym. Sci., 49-50, 1 (2015).
W. Wu, W. Wang, and J. Li, Prog. Polym. Sci., 46, 55 (2015).
M. J. Derry, L. A. Fielding, and S. P. Armes, Prog. Polym. Sci., 52, 1 (2016).
K. Kim, W. C. W. Chen, Y. Heo, and Y. Wang, Prog. Polym. Sci., 60, 18 (2016).
M. A. Tasdelen, B. Kiskan, and Y. Yagci, Prog. Polym. Sci., 52, 19 (2016).
Y.-J. Wang, M. Larsson, W.-T. Huang, S.-H. Chiou, S.J. Nicholls, J.-I. Chao, and D.-M. Liu, Prog. Polym. Sci., 57, 153 (2016).
S. G. Roos, A. H. E. Mueller, and K. Matyjaszewski, Macromolecules, 32, 8331 (1999).
M. J. Ziegler and K. Matyjaszewski, Macromolecules, 34, 415 (2001).
S. Coca, H.-J. Paik, and K. Matyjaszewski, Macromolecules, 30, 6513 (1997).
S. Coca and K. Matyjaszewski, Macromolecules, 30, 2808 (1997).
W. Tang, Y. Kwak, W. Braunecker, N. V. Tsarevsky, M. L. Coote, and K. Matyjaszewski, J. Am. Chem. Soc., 130, 10702 (2008).
W. Tang and K. Matyjaszewski, Macromolecules, 40, 1858 (2007).
W. Tang and K. Matyjaszewski, Macromolecules, 39, 4953 (2006).
L. Mueller and K. Matyjaszewski, Macromol. React. Eng., 4, 180 (2010).
V. A. Williams, T. G. Ribelli, P. Chmielarz, S. Park, and K. Matyjaszewski, J. Am. Chem. Soc., 137, 1428 (2015).
X. Pan, N. Malhotra, A. Simakova, Z. Wang, D. Konkolewicz, and K. Matyjaszewski, J. Am. Chem. Soc., 137, 15430 (2015).
A. Kaur, T.G. Ribelli, K. Schroder, K. Matyjaszewski, and T. Pintauer, Inorg. Chem., 54, 1474 (2015).
K. Schröder, R.T. Mathers, J. Buback, D. Konkolewicz, A. J. D. Magenau, and K. Matyjaszewski, ACS Macro Lett., 1, 1037 (2012).
J. Xia and K. Matyjaszewski, Macromolecules, 32, 2434 (1999).
W. Jakubowski, K. Min, and K. Matyjaszewski, Macromolecules, 39, 39 (2006).
K. Matyjaszewski, W. Jakubowski, K. Min, W. Tang, J. Y. Huang, W. A. Braunecker, and N. V. Tsarevsky, Proc. Natl. Acad. Sci. U.S.A., 103, 15309 (2006).
K. Matyjaszewski, S. Coca, S. G. Gaynor, M. L. Wei, and B. E. Woodworth, Macromolecules, 30, 7348 (1997).
A. Nese, Y. C. Li, S. S. Sheiko, and K. Matyjaszewski, ACS Macro Lett., 1, 991 (2012).
D. Konkolewicz, Y. Wang, M. Zhong, P. Krys, A. A. Isse, A. Gennaro, and K. Matyjaszewski, Macromolecules, 46, 8749 (2013).
D. Konkolewicz, P. Krys, J. R. Góis, P.V. Mendonça, M. Zhong, Y. Wang, A. Gennaro, A. A. Isse, M. Fantin, and K. Matyjaszewski, Macromolecules, 47, 560 (2014).
D. Konkolewicz, Y. Wang, P. Krys, M. Zhong, A. A. Isse, A. Gennaro, and K. Matyjaszewski, Polym. Chem., 5, 4396 (2014).
A. J. D. Magenau, N. C. Strandwitz, A. Gennaro, and K. Matyjaszewski, Science, 332, 81 (2011).
P. Chmielarz, M. Fantin, S. Park, A. A. Isse, A. Gennaro, A. J. D. Magenau, A. Sobkowiak, and K. Matyjaszewski, Prog. Polym. Sci., 69, 47 (2017).
M. Fantin, P. Chmielarz, Y. Wang, F. Lorandi, A. A. Isse, A. Gennaro, and K. Matyjaszewski, Macromolecules, 50, 3726 (2017).
M. Fantin, S. Park, Y. Wang, and K. Matyjaszewski, Macromolecules, 49, 8838 (2016).
Z. Wang, X. Pan, J. Yan, S. Dadashi-Silab, G. Xie, J. Zhang, Z. Wang, H. Xia, and K. Matyjaszewski, ACS Macro Lett., 6, 546 (2017).
J. Mosnacek and M. Ilcikova, Macromolecules, 45, 5859 (2012).
D. Konkolewicz, K. Schroder, J. Buback, S. Bernhard, and K. Matyjaszewski, ACS Macro Lett., 1, 1219 (2012).
M. Fantin, A. A. Isse, N. Bortolamei, K. Matyjaszewski, and A. Gennaro, Electrochim. Acta, 222, 393 (2016).
J. Qiu, K. Matyjaszewski, L. Thouin, and C. Amatore, Macromol. Chem. Phys., 201, 1625 (2000).
T. Pintauer and K. Matyjaszewski, Coord. Chem. Rev., 249, 1155 (2005).
T. Pintauer and K. Matyjaszewski, Chem. Soc. Rev., 37, 1087 (2008).
K. Schroder, D. Konkolewicz, R. Poli, and K. Matyjaszewski, Organometallics, 31, 7994 (2012).
Y. Inoue and K. Matyjaszewski, Macromolecules, 36, 7432 (2003).
Y. Inoue and K. Matyjaszewski, Macromolecules, 37, 4014 (2004).
T. Sarbu and K. Matyjaszewski, Macromol. Chem. Phys., 202, 3379 (2001).
Y. Wang and K. Matyjaszewski, Macromolecules, 43, 4003 (2010).
Z. G. Xue, B. W. Lee, S. K. Noh, and W. S. Lyoo, Polymer, 48, 4704 (2007).
K. Satoh, H. Aoshima, and M. Kamigaito, J. Polym. Sci., Part A: Polym. Chem., 46, 6358 (2008).
C. Uchiike, M. Ouchi, T. Ando, M. Kamigaito, and M. Sawamoto, J. Polym. Sci., Part A: Polym. Chem., 46, 6819 (2008).
D. He, Z. Xue, M. Y. Khan, S. K. Noh, and W. S. Lyoo, J. Polym. Sci., Part A: Polym. Chem., 48, 144 (2010).
G. H. Zhu, L. F. Zhang, Z. B. Zhang, J. Zhu, Y. F. Tu, Z. P. Cheng, and X. L. Zhu, Macromolecules, 44, 3233 (2011).
Y. Wang, Y. Kwak, and K. Matyjaszewski, Macromolecules, 45, 5911 (2012).
K. Nishizawa, M. Ouchi, and M. Sawamoto, Macromolecules, 46, 3342 (2013).
Y. Kotani, M. Kamigaito, and M. Sawamoto, Macromolecules, 32, 6877 (1999).
I. Onishi, K.-Y. Baek, Y. Kotani, M. Kamigaito, and M. Sawamoto, J. Polym. Sci., Part A: Polym. Chem., 40, 2033 (2002).
Y. Fuji, T. Ando, M. Kamigaito, and M. Sawamoto, Macromolecules, 35, 2949 (2002).
M. Wakioka, K.Y. Baek, T. Ando, M. Kamigaito, and M. Sawamoto, Macromolecules, 35, 330 (2002).
M. Ishio, T. Terashima, M. Ouchi, and M. Sawamoto, Polym. J., 42, 17 (2010).
K. Matyjaszewski, M. Wei, J. Xia, and N. E. McDermott, Macromolecules, 30, 8161 (1997).
K. Ibrahim, K. Yliheikkila, A. Abu-Surrah, B. Lofgren, K. Lappalainen, M. Leskela, T. Repo, and J. Seppala, Eur. Polym. J., 40, 1095 (2004).
S. Niibayashi, H. Hayakawa, R. H. Jin, and H. Nagashima, Chem. Commun., 1855 (2007).
R. Luo and A. Sen, Macromolecules, 41, 4514 (2008).
L. Zhang, Z. Cheng, Y. Lu, and X. Zhu, Macromol. Rapid Commun., 30, 543 (2009).
H. Aoshima, K. Satoh, T. Umemura, and M. Kamigaito, Polym. Chem., 4, 3554 (2013).
G.-X. Wang, M. Lu, L.-C. Liu, H. Wu, and M. Zhong, J. Appl. Polym. Sci., 128, 3077 (2013).
Y. Sunada, H. Tsutsumi, K. Shigeta, R. Yoshida, T. Hashimoto, and H. Nagashima, Dalton Trans., 42, 16687 (2013).
V. C. Gibson, R. K. O'Reilly, W. Reed, D. F. Wass, A. J. White, and D. J. Williams, Chem. Commun., 1850 (2002).
R. K. O'Reilly, V. C. Gibson, A. J. P. White, and D. J. Williams, J. Am. Chem. Soc., 125, 8450 (2003).
L. E. N. Allan, M. P. Shaver, A. J. P. White, and V. C. Gibson, Inorg. Chem., 46, 8963 (2007).
M. P. Shaver, L. E. N. Allan, and V. C. Gibson, Organometallics, 26, 4725 (2007).
R. Ferro, S. Milione, L. Erra, and A. Grassi, Inorg. Chem. Commun., 11, 535 (2008).
J. A. Akkara, J. Z. Wang, D. P. Yang, and K. E. Gonsalves, Macromolecules, 33, 2377 (2000).
R. M. Islamova, S. V. Nazarova, and O. I. Koifman, Macroheterocycles, 4, 97 (2011).
K. Yamashita, K. Yamamoto, and J. Kadokawa, Polymer, 54, 1775 (2013).
A. Simakova, M. Mackenzie, S. E. Averick, S. Park, and K. Matyjaszewski, Angew. Chem. Int. Ed. Engl., 52, 12148 (2013).
S.-H. Qin, D.-Q. Qin, and K.-Y. Qiu, New J. Chem., 25, 893 (2001).
D. Q. Qin, S. H. Qin, and K. Y. Qiu, J. Polym. Sci., Part A: Polym. Chem., 39, 3464 (2001).
J. Cao, L. Zhang, X. Jiang, C. Tian, X. Zhao, Q. Ke, X. Pan, Z. Cheng, and X. Zhu, Macromol. Rapid Commun., 34, 1747 (2013).
S. M. Zhu and D. Y. Yan, J. Polym. Sci., Part A: Polym. Chem., 38, 4308 (2000).
G. Zong, H. Chen, C. Wang, D. Liu, and Z. Hao, J. Appl. Polym. Sci., 118, 3673 (2010).
Z. J. Deng, J. N. Guo, L. H. Qiu, C. Yuan, Y. X. Zhou, and F. Yan, J. Polym. Sci., Part A: Polym. Chem., 51, 664 (2013).
J. Ma, H. Chen, G. X. Zong, C. H. Wang, and D. L. Liu, J. Macromol. Sci., Part A: Pure. Appl. Chem., 47, 1075 (2010).
G. Wang, X. L. Zhu, Z. P. Cheng, and I. Zhu, J. Polym. Sci., Part A: Polym. Chem., 44, 2912 (2006).
C. Hou, R. J. Qu, C. N. Ji, C. H. Wang, and C. G. Wang, J. Polym. Sci., Part A: Polym. Chem., 44, 219 (2006).
J. Louie and R. H. Grubbs, Chem. Commun., 1479 (2000).
S. Okada, S. Park, and K. Matyjaszewski, ACS Macro Lett., 3, 944 (2014).
A. Simakova, M. Mackenzie, S. E. Averick, S. Park, and K. Matyjaszewski, Angew. Chem. Int. Ed., 52, 12148 (2013).
M. Teodorescu, S. G. Gaynor, and K. Matyjaszewski, Macromolecules, 33, 2335 (2000).
Y. Wang and K. Matyjaszewski, Macromolecules, 44, 1226 (2011).
Y. Wang, Y.Z. Zhang, B. Parker, and K. Matyjaszewski, Macromolecules, 44, 4022 (2011).
K. Mukumoto, Y. Wang, and K. Matyjaszewski, ACS Macro Lett., 1, 599 (2012).
H. Yu, Z. Zhang, Z. Cheng, J. Zhu, N. Zhou, W. Zhang, and X. Zhu, J. Polym. Sci., Part A: Polym. Chem., 50, 2182 (2012).
L. J. Bai, L. F. Zhang, Z. B. Zhang, Y. F. Tu, N. C. Zhou, Z. P. Cheng, and X. L. Zhu, Macromolecules, 43, 9283 (2010).
M. Ishio, M. Katsube, M. Ouchi, M. Sawamoto, and Y. Inoue, Macromolecules, 42, 188 (2009).
M. Fantin, S. Park, Y. Wang, and K. Matyjaszewski, Macromolecules, 49, 8838 (2016).
L. E. Allan, J. P. MacDonald, A. M. Reckling, C. M. Kozak, and M. P. Shaver, Macromol. Rapid Commun., 33, 414 (2012).
L. E. N. Allan, J. P. MacDonald, G. S. Nichol, and M. P. Shaver, Macromolecules, 47, 1249 (2014).
R. Poli and M. P. Shaver, Inorg. Chem., 53, 7580 (2014).
H. Schroeder, M. Buback, and M. P. Shaver, Macromolecules, 48, 6114 (2015).
H. Schroeder, B. R. M. Lake, S. Demeshko, M. P. Shaver, and M. Buback, Macromolecules, 48, 4329 (2015).
R. Mayilmurugan, K. Visvaganesan, E. Suresh, and M. Palaniandavar, Inorg. Chem., 48, 8771 (2009).
M. J. Zhong and K. Matyjaszewski, Macromolecules, 44, 2668 (2011).
Author information
Authors and Affiliations
Corresponding author
Additional information
Acknowledgments: Support from NSF (CHE 1707490) is gratefully acknowledged.
Rights and permissions
About this article
Cite this article
Nishiura, C., Williams, V. & Matyjaszewski, K. Iron and copper based catalysts containing anionic phenolate ligands for atom transfer radical polymerization. Macromol. Res. 25, 504–512 (2017). https://doi.org/10.1007/s13233-017-5118-5
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13233-017-5118-5