Abstract
A dinuclear manganese complex [Mn2(CO)10] induced the controlled/living radical polymerization of various conjugated and unconjugated vinyl monomers including vinyl acetate, methyl acrylate, and styrene in conjunction with dithiocarbonyl compounds [R-SC(S)Z] under weak visible light at 40 °C. The obtained polymers had controlled molecular weights, narrow molecular weight distributions, and well-defined chain-end groups originating from R-SC(S)Z, as indicated by SEC, 1H NMR, and MALDI-TOF-MS analyses. The polymerization most probably proceeds via the reversible activation of the C-SC(S)Z bond by ·Mn(CO)5 via the metal-catalyzed process and/or by the carbon-centered radical species via the addition-fragmentation chain transfer (RAFT) process.
Similar content being viewed by others
Article PDF
References
C. J. Hawker, J. Am. Chem. Soc., 116, 11185 (1994).
C. J. Hawker, A. W. Bosman, and E. Harth, Chem. Rev., 101, 3661 (2001).
A. Studer and T. Schulte, Chem. Rec., 5, 27 (2005).
M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995).
M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rev., 101, 3689 (2001).
M. Kamigaito, T. Ando, and M. Sawamoto, Chem. Rec., 4, 159 (2004).
M. Ouchi, T. Terashima, and M. Sawamoto, Ace Chem. Res., 41, 1120 (2008).
J.-S Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
K. Matyjaszewski and J. Xia, Chem. Rev., 101, 2921 (2001).
N. V. Tsarevsky and K. Matyjaszewski, Chem. Rev., 107, 2270 (2007).
W. A. Braunecker and K. Matyjaszewski, Prog. Polym. Scl., 32, 93 (2007).
V. Percec and B. Barboiu, Macromolecules., 28, 7970 (1995).
C. Granel, Ph. Dubois, R. Jérôme, and Ph. Teyssié, Macromolecules, 29, 8576 (1996).
D. M. Haddleton, C. B. Jasieczek, M. J. Hannon, and A. J. Shooer, Macromolecules., 30, 2190 (1997).
T. Ando, M. Kamigaito, and M. Sawamoto, Macromolecules., 30, 4507 (1997).
Y. Kotani, M. Kamigaito, and M. Sawamoto, Macromolecules., 32, 6877 (1999).
Y. Kotani, M. Kamigaito, and M. Sawamoto, Macromolecules., 33, 3543 (2000).
M. Kamigaito, I. Onishi, S. Kimura, and M. Sawamoto, Chem. Commun., 2694 (2002).
K. Matyjaszewski, M. Wei, J. Xia, and N. E. McDermott, Macromolecules, 30, 8161 (1997).
M. Teodorescu, S. G. Gaynor, and K. Matyjaszewski, Macromolecules., 33, 2335 (2000).
J. Louie and R. H. Grubbs, Chem. Commun., 1479 (2000).
S. Zhu, D. Yan, G. Zhang, and M. Li, Macromol. Chem. Phys., 201, 2666 (2000).
V. C. Gibson, R. K. O'Reilly, W. Reed, D. F. Wass, A. J. P. 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).
R. K. O'Reilly, V. C. Gibson, A. J. P. White, and D. J. Williams, Polyhedron., 23, 2921 (2004).
S. Niibayashi, H. Hayakawa, R.-H. Jina, and H. Nagashima, Chem. Commun., 1855 (2007).
H. Uegaki, Y. Kotani, M. Kamigaito, and M. Sawamoto, Macromolecules., 30, 2249 (1997).
H. Uegaki, Y. Kotani, M. Kamigaito, and M. Sawamoto, Macromolecules., 31, 6756 (1998).
H. Uegaki, M. Kamigaito, and M. Sawamoto, J. Polym. Sei, Part A: Polym. Chem., 37, 3003 (1999).
P. Li and K. Y. Qiu, Polymer., 43, 5873 (2002).
R. K. O'Reilly, M. P. Shaver, and V. C. Gibson, Inorg. Chim. Acta., 359, 4417 (2006).
V. Percec, B. Barboiu, A. Neumann, J. C. Ronda, and M. Zhao, Macromolecules., 29, 3665 (1996).
G. Moineau, C. Granel, Ph. Dubois, R. Jerome, and Ph. Teyssié, Macromolecules, 31, 542 (1998).
M. G. L. Petrucci, A.-M. Lebuis, and A. K. Kakkar, Organo-metallics., 17, 4966 (1998).
Ph. Lecomte, I. Drapier, Ph. Dubois, R. Jérôme, and Ph. Teyssié, Macromolecules., 30, 7631 (1997).
J. A. M. Brandts, P. van de Geijn, E. E. van Faassen, J. Boersma, and G. van Koten, J. Organomet. Chem., 584, 246 (1999).
E. Le Grognec, J. Claverie, and R. Poli, J. Am. Chem. Soc., 123, 9513 (2001).
F. Stoffelbach, D. M. Haddleton, and R. Poli, Eur. Polym. J., 39, 2099 (2003).
J. A. Mata, S. Maria, J.-C. Daran, and R. Poli, Eur. J. Inorg. Chem., 2624 (2006).
B. Wang, Y. Zhuang, X. Luo, S. Xu, and X. Zhou, Macromolecules., 36, 9684 (2003).
M.-S. Weiser and R. Miiljaupt, J. Polym. Sel, Part A: Polym. Chem., 43, 3804 (2005).
K. Matsubara and M. Matsumoto, J. Polym. Sel, Part A: Polym. Chem., 44, 4222 (2006).
Y. Kotani, M. Kamigaito, and M. Sawamoto, Macromolecules., 32, 2420 (1999).
S. Komiya, T. Chigira, T. Suzuki, and M. Hirano, Chem. Lett., 28, 347 (1999).
J. Chiefari, Y. K. Chong, F. Ercole, J. Krstina, J. Jeffery, T. P. T. Le, R. T. A. Mayadunne, G. F. Meijs, C. L. Moad, G. Moad, E. Rizzardo, and S. H. Thang, Macromolecules., 31, 5559 (1998).
G. Moad, E. Rizzardo, and S. H. Thang, Aust. J. Chem., 58, 379 (2005).
G. Moad, E. Rizzard, and S. H. Thang, Polymer., 49, 1079 (2008).
G. Moad, E. Rizzardo, and S. H. Thang, Ace Chem. Res., 41, 1133 (2008).
M. Destarac, C. Brochon, J.-M. Catala, A. Wilczewska, and S. Z. Zard, Macromol. Chem. Phys., 203, 2281 (2002).
K. A. Davis and K. Matyjaszewski, J. Macromol. Sei., Part A: Pure Appl. Chem., 41, 449 (2004).
W. Tang and K. Matyjaszewski, Macromolecules., 40, 1858 (2007).
E. Rizzardo, J. Chiefari, R. T. A. Mayadunne, G. Moad, and S. H. Thang, “ACS Symposium Series”, 768, American Chemical Society Publication, 2000, p 278.
D. Charmot, P. Corpart, H. Adam, S. Zard, T. Biadatti, and G. Bouhadir, Macromol. Symp., 150, 23 (2000).
M. Destarac, D. Charmot, X. Frank, and S. Z. Zard, Macromol. Rapid Commun., 21, 1035 (2000).
M. H. Stenzel, L. Cummins, G. E. Roberts, T. P. Davis, P. Vana, and C. Barner-Kowollik, Macromol. Chem. Phys., 204, 1160 (2003).
M. L. Coote and L. Radom, Macromolecules., 37, 590 (2004).
A. Favier, C. Barner-Kowollik, T. Davis, and M. H. Stenzel, Macromol. Chem. Phys., 205, 925 (2004).
R. W. Simms, T. P. Davis, and M. F. Cunningham, Macromol. Rapid Commun., 26, 592 (2005).
D. Boschmann and P. Vana, Polym. Bull., 53, 231 (2005).
J. P. Russum, N. D. Barbre, C. W. Jones, and F. J. Schork, J. Polym. Sel, Part A: Polym. Chem., 43, 2188 (2005).
F. Chen, Z. Cheng, J. Zhu, W. Zhang, and X. Zhu, Eur. Polym. J., 44, 1789 (2008).
Y. K. Chong, J. Krstina, T. P. T. Le, G. Moad, A. Postma, E. Rizzardo, and S. H. Thang, Macromolecules., 36, 2256 (2003).
J. F. Quinn, E. Rizzardo, and T. P. Davis, Chem. Commun., 1044 (2001).
K. Koumura, K. Satoh, and M. Kamigaito, Macromolecules., 41, 7359 (2008).
E. W. Abel and F. G. A. Stone, Q. Rev., Chem. Soc., 23, 325 (1969).
M. Wrighton, Chem. Rev., 74, 401 (1974).
T. J. Meyer and J. V. Caspar, Chem. Rev., 85, 187 (1985).
A. E. Stiegman and D. R. Tyler, Coord. Chem. Rev., 63, 217 (1985).
B. C. Gilbert and A. F. Parsons, J. Chem. Soc, Perkin Trans. 2, 367 (2002).
T. E. Bitterwolf, J. Organomet. Chem., 689, 3939 (2004).
S. A. Hallock and A. Wojcicki, J. Organomet. Chem., 54, C27 (1973).
M. S. Wrighton and D. S. Ginley, J. Am. Chem. Soc., 97, 2065 (1975).
S. B. McCullen and T. L. Brown, Inorg. Chem., 20, 3528 (1981).
T. Kondo, Y. Sone, Y. Tsuji, and Y. Watanabe, J. Organomet. Chem., 473, 163 (1994).
B. C. Gilbert, W. Kalz, C. I. Lindsay, P. T. McGrail, A. F. Parsons, and D. T. E. Whittaker, Tetrahedron Lett., 40, 6095 (1999).
N. Huther, P. T. McGrail, and A. F. Parsons, Tetrahedron Lett., 43, 2535 (2002).
N. Huther, P. T. McGrail, and A. F. Parsons, Eur. J. Org. Chem., 1740 (2004).
M. Nishimura, M. Kamigaito, and M. Sawamoto, The 218th ACS National Meeting, Polymer Preprints, New Orleans, LA, USA, 470 (1999).
D.-Q. Qin, S.-H. Qin, and K.-Y. Qiu, J. Polym. Sci., Part A: Polym Chem., 39, 3464 (2001).
P. Li and K.-Y. Qiu, J. Polym. Sci., Part A: Polym. Chem., 40, 2093 (2002).
P. Li, S.-H. Qin, D.-Q. Qin, and K.-Y. Qiu, Polym. Int., 53, 756 (2004).
W. Zhang, N. Zhou, J. Zhu, B. Sun, and X. Zhu, J. Polym. Sci., Part A: Polym. Chem., 44, 510 (2006).
W. Zhang, X. Zhu, Z. Cheng, and J. Zhu, J. Appl. Polym. Sci., 106, 230 (2007).
Y. Kwak and K. Matyjaszewski, Macromolecules., 41, 6627 (2008).
R. Nicolaÿ, Y. Kwak, and K. Matyjaszewski, Macromolecules., 41, 4585 (2008).
Y. Kwak, R. Nicolaÿ, and K. Matyjaszewski, Macromolecules., 41, 6602 (2008).
M. Wakioka, K.-Y. Baek, T. Ando, M. Kamigaito, and M. Sawamoto, Macromolecules., 35, 330 (2002).
D. W. Ovenall, Macromolecules., 17, 1458 (1984).
R. L. Adelman and R. C. Ferguson, J. Polym. Sci., Polym. Chem. Ed., 13, 891 (1975).
F. F. Vercauteren and W. A. B. Donners, Polymer., 27, 993 (1986).
S. Amiya and M. Uetsuki, Macromolecules., 15, 166 (1982).
S. Amiya and M. Uetsuki, Anal. Sci., 1, 91 (1985).
N. Ueda, M. Kamigaito, and M. Sawamoto, The 37th IUPAC International Symposium on Macromolecules, Preprints, Gold Coast, Australia, 237 (1998).
N. Ueda, JP Patents 10 060 021 (1996).
N. Ueda, JP Patents 11 147 914 (1997).
N. Ueda, JP Patents 11 171 926 (1997).
M. C. Iovu and K. Matyjaszewski, Macromolecules., 36, 9346 (2003).
K. Koumura, K. Satoh, M. Kamigaito, and Y. Okamoto, Macromolecules, 39, 4054 (2006).
M. Destarac, W. Bzducha, D. Taton, I. Gauthier-Gillaizeau, and S. Z. Zard, Macromol. Rapid Commun., 23, 1049 (2002).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Koumura, K., Satoh, K. & Kamigaito, M. Mn2(CO)10-Induced RAFT Polymerization of Vinyl Acetate, Methyl Acrylate, and Styrene. Polym J 41, 595–603 (2009). https://doi.org/10.1295/polymj.PJ2009070
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.PJ2009070
Keywords
This article is cited by
-
A novel solid state photocatalyst for living radical polymerization under UV irradiation
Scientific Reports (2016)
-
Recent developments in metal-catalyzed living radical polymerization
Polymer Journal (2011)