Abstract
Polymerization of methyl methacrylate (MMA) with a radical initiator covalently immobilized 4,4′-azobis(4-cyanopetanoyl) (ACP) group on the inside wall of MCM-41 (ACP-MCM-41) was investigated. The polymerization of MMA with ACP-MCM-41 proceeded to give high-molecular weight polymers. The relationship between the Mn of the resulting polymer and the polymer yield gave a straight line, and the line passed through the origin, which is in contrast to that such relationship was not observed in the polymerization of MMA with dimethyl 2,2′-azobis(2-methyl propionate) (MAIB) even in the cavity of MCM-41. The results demonstrates that the termination reactions of the propagating radicals were extremely suppressed by movement restriction of the polymer chains covalently immobilized on the inside wall of MCM-41 in the polymerization of MMA. The presence of super long-lived propagating radical on the inside wall of MCM-41 was confirmed by ESR measurement and post-polymerization.
Similar content being viewed by others
Article PDF
References
A. P. Wight and M. E. Davis, Chem. Rev., 102, 3589 (2002).
C. T. Kresge, M. E. Leonowicz, W. J. Roth, J. C. Vartuli, and J. S. Beck, Nature, 359, 710 (1992).
J. S. Beck, J. C. Vartuli, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K. D. Schmitt, C. T.-W. Chu, D. H. Olson, E. W. Sheppard, S. B. McCullen, J. B. Higgins, and J. L. Schlenker, J. Am. Chem. Soc., 114, 10834 (1992).
T. Yanagisawa, T. Shimizu, K. Kuroda, and D. Kato, Bull. Chem. Soc. Jpn., 63, 988 (1990).
T. Maschmeyer, F. Rey, G. Ssnker, and J. M. Thomas, Nature, 378, 159 (1995).
X. Feng, G. E. Fryxell, L.-Q. Wang, A. Y. Kim, J. Liu, and K. M. Kemner, Science, 276, 923 (1997).
N. Liu, Z. Chen, D. R. Dunphy, Y. B. Jiang, R. A. Assink, and C. J. Brinker, Angew. Chem., Int. Ed., 42, 1731 (2003).
N. Liu, D. R. Dunphy, P. Atanassov, S. D. Bunge, Z. Chen, G. P. Lopez, T. J. Boyle, and C. J. Brinker, Nano Lett., 4, 551 (2004).
N. K. Mai, M. Fujiwara, and Y. Tanaka, Nature, 421, 350 (2003).
K. Inumaru, J. Kiyoto, and S. Yamanaka, Chem. Commun., 903 (2000).
K. Inumaru, Y. Inoue, S. Kakii, T. Nakano, and S. Yamanaka, Chem. Lett., 32, 1110 (2003).
K. Kageyama, J. Tamazawa, and T. Aida, Science, 285, 2113 (1999).
Y. S. Ko, T. K. Han, J. W. Park, and S. I. Woo, Macromol. Rapid Commun., 17, 749 (1996).
J. Tudor and D. O'Hare, Chem. Commun., 603 (1997).
S. O'Brien, J. Tudor, T. Maschmeyer, and D. O'Hare, Chem. Commun., 1905 (1997).
C. J. Miller and D. O'Hare, Chem. Commun., 1710 (2004).
L. K. Van Looveren, D. F. Geysen, K. A. Vercruysse, B. H. Wouters, P. Grobet, and P. A. Jacobs, Angew. Chem., Int. Ed., 37, 517 (1998).
M. Kwanten, B. A. M. Carrière, P. J. Grobet, and P. A. Jacobs, Chem. Commun., 1508 (2003).
R. R. Rao, B. M. Weckhuysen, and R. A. Schoonheydt, Chem. Commun., 445 (1999).
B. M. Weckhuysen, R. R. Rao, J. Pelgrims, R. A. Schoonheydt, P. Bodart, G. Debras, O. Collait, P. V. D. Voort, and E. F. Vansant, Chem. Eur. J., 6, 2960 (2000).
M. Pillinger, I. S. Gonçalves, P. Ferreira, J. Rocha, M. Schäfer, D. Schön, O. Nuyken, and F. E. Kühn, Macromol. Rapid Commun., 22, 1302 (2001).
M. Pillinger, I. S. Gonçalves, A. D. Lopes, P. Ferreira, J. Rocha, G. Zhang, M. Schäfer, O. Nuyken, and F. E. Kühn, Phys. Chem. Chem. Phys., 4, 696 (2002).
H. Balcar, J. Sedláček, J. Čejka, and J. Vohlídal, Macromol. Rapid Commun., 23, 32 (2002).
Z. Ye, H. Alayouri, S. Zhu, and Y. S. Lin, Polymer, 44, 969 (2003).
D. J. Cardin, S. P. Constantine, A. Gilbert, A. K. Lay, M. Alvaro, M. S. Galletero, H. Garcia, and F. Marquez, J. Am. Chem. Soc., 123, 3141 (2001).
K. Moller, T. Bein, and R. X. Fischer, Chem. Mater., 10, 1841 (1998).
P. L. Llewellyn, U. Ciesla, H. Becher, R. Stadler, F. Schüth, and K. K. Unger, Stud. Surf. Sci. Catal., 84, 2013 (1994).
M. Choi, F. Kleitz, D. Liu, H. Y. Lee, W. Ahn, and R. Ryoo, J. Am. Chem. Soc., 127, 1924 (2005).
W. C. Molenkamp, M. Watanabe, H. Miyata, and S. H. Tolbert, J. Am. Chem. Soc., 126, 4476 (2004).
E. J. Acosta, C. S. Carr, E. E. Simanek, and D. F. Shantz, Adv. Mater., 16, 985 (2004).
O. Prucker and J. Rühe, Macromolecules, 31, 592 (1998).
B. Zhao and W. J. Brittain, Prog. Polym. Sci., 25, 677 (2000).
M. Ejaz, Y. Tsujii, and T. Fukuda, Polymer, 42, 6811 (2001).
G. Carrot, S. Diamanti, M. Manuszak, B. Charleux, and J.-P. Vairon, J. Polym. Sci., Part A: Polym. Chem., 39, 4294 (2001).
T. von Werne and T. E. Patten, J. Am. Chem. Soc., 123, 7497 (2001).
K. Ohno, T. Morinaga, K. Koh, Y. Tsujii, and T. Fukuda, Macromolecules, 38, 2137 (2005).
M. Save, G. Granvorka, J. Bernard, B. Charleux, C. Boissière, D. Grosso, and C. Sanchez, Macromol. Rapid Commun., 27, 393 (2006).
S. Blomberg, S. Ostberg, E. Harth, A. W. Bosman, B. Van Horn, and C. J. Hawker, J. Polym. Sci., Part A: Polym. Chem., 40, 1309 (2002).
Q. Fu, G. V. R. Rao, L. K. Ista, Y. Wu, B. P. Andrzejewski, L. A. Sklar, T. L. Ward, and G. P. López, Adv. Mater., 15, 1262 (2003).
M. Kruk, B. Dufour, E. B. Celer, T. Kowalewski, M. Jaroniec, and K. Matyjaszewski, J. Phys. Chem. B, 109, 9216 (2005).
S. M. Ng, S. Ogino, and T. Aida, Macromol. Rapid. Commun., 18, 991 (1997).
T. R. Pauly, V. Petkov, Y. Liu, S. J. L. Billinge, and T. J. Pinnavaia, J. Am. Chem. Soc., 124, 97 (2002).
S. Spange, A. Gräser, H. Müller, Y. Zimmermann, P. Rehak, C. Jäger, H. Fuess, and C. Baehtz, Chem. Mater., 13, 3698 (2001).
D. A. Smith, Makromol. Chem., 103, 301 (1967).
M. Kato, M. Kamigaito, M. Sawamoto, and T. Higashimura, Macromolecules, 28, 1721 (1995).
J.-S. Wang and K. Matyjaszewski, J. Am. Chem. Soc., 117, 5614 (1995).
M. K. Georges, R. P. N. Veregin, P. M. Kazmaier, and G. K. Hamer, Macromolecules, 26, 2987 (1993).
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).
M. Kamachi, M. Kohno, D. J. Liaw, and S. Katsuki, Polym. J., 10, 69 (1978).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ikeda, K., Kida, M. & Endo, K. Polymerization of Methyl Methacrylate with Radical Initiator Immobilized on the Inside Wall of Mesoporous Silica. Polym J 41, 672–678 (2009). https://doi.org/10.1295/polymj.PJ2008332
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.PJ2008332