Abstract
Vinyl-functionalized cubic silsesquioxanes were prepared from octakis(dimethylsiloxy)octasilsesquioxane via hydrosilylation with 6, 5, and 4 equiv. of allylbenzene followed by the reaction with excess 1,5-hexadiene. The content of hexenyl groups in the silsesquioxanes was determined by 1H NMR and MALDI-TOF MS. Polyaddition by hydrosilylation of these compounds with bis(dimethylsilyl)benzene afforded polymers with moderate molecular weight soluble in common organic solvents. Chemical structure and thermal stability of the polymers were characterized by NMR, IR, and TGA.
Similar content being viewed by others
Article PDF
References
P. G. Harrison, J. Organomet. Chem., 542, 141 (1997).
D. Hoebbel, K. Endres, T. Reinert, and I. Pitsch, J. Non-Cryst. Solids, 176, 179 (1994).
P. G. Harrison and R. Kannengiesser, Chem. Commun, 1996, 415.
G. Z. Li, L. Wang, H. Toghiani, T. L. Daulton, K. Koyama, and C. U. Pittman, Jr., Macromolecules, 34, 8686 (2001).
C. Zhang, F. Babonneau, C. Bonhomme, R. M. Laine, C. L. Soles, H. A. Hristov, and A. F. Yee, J. Am. Chem. Soc., 120, 8380 (1998).
C. Zhang and R. M. Laine, J. Am. Chem. Soc., 122, 6979 (2000).
J. Choi, J. Harcup, A. F. Yee, Q. Zhu, and R. M. Laine, J. Am. Chem. Soc, 123, 11420 (2001).
R. Tamaki, Y. Tanaka, M. Z. Asuncion, J. Choi, and R. M. Laine, J. Am. Chem. Soc., 123, 12416 (2001).
A. Sellinger and R. M. Laine, Macromolecules, 29, 2327 (1996).
R. O. R. Costa, W. L. Vasconcelos, R. Tamaki, and R. M. Laine, Macromolecules, 34, 5398 (2001).
A. Sellinger and R. M. Laine, Chem. Mater., 8, 1592 (1996).
R. Tamaki, J. Choi, and R. M. Laine, Chem. Mater., 15, 793 (2003).
R. M. Laine, C. Zhang, A. Sellinger, and L. Viculis, Appl. Organometal. Chem., 12, 715 (1998).
J. V. Crivello and R. Malik, J. Polym. Sci., Part A: Polym. Chem., 35, 407 (1997).
D. Neumann, M. Fisher, L. Tran, and J. G. Matisons, J. Am. Chem. Soc., 124, 13998 (2002).
J. D. Lichtenhan, Y. A. Otonari, and M. J. Carr, Macromolecules, 28, 8435 (1995).
T. S. Haddad and J. D. Lichtenhan, Macromolecules, 29, 7302 (1996).
A. Tsuchida, C. Bolln, F. G. Sernetz, H. Frey, and R. Mülhaupt, Macromolecules, 30, 2818 (1997).
P. T. Mather, H. G. Jeon, A. Romo-Uribe, T. S. Haddad, and J. D. Lichtenhan, Macromolesules, 32, 1194 (1999).
J. Pyun and K. Matyjaszewski, Macromolecules, 33, 217 (2000).
L. Zheng, R. J. Farris, and E. B. Coughlin, Macermolecules, 34, 8034 (2001).
L. Zheng, A. J. Waddon, R. J. Farris, and E. B. Coughlin, Macromolecules, 35, 2375 (2002).
H. Xu, S. Kuo, J. Lee, and F. Chang, Macromolecules, 35, 8788 (2002).
W. Zhang, B. X. Fu, Y. Seo, E. Schrag, B. Hsiao, P. T. Mather, N. Yang, D. Xu, H. Ade, M. Rafailovich, and J. Sokolov, Macromolecules, 35, 8029 (2002).
M. J. Abad, L. Barral, D. P. Fasce, and R. J. J. Williams, Macromolecules, 36, 3128 (2003).
J. B. Carroll, A. J. Waddon, H. Nakade, and V. M. Rotello, Macromolecules, 36, 6289 (2003).
B. X. Fu, B. S. Hsiao, S. Pagola, P. Stephens, H. White, M. Rafailovich, J. Sokolov, R. T. Mather, H. G. Jeon, S. Phillips, J. Lichtenhan, and J. Schwab, Polymer, 42, 599 (2001).
C. Leu, Y. Chang, and K. Wei, Chem. Mater., 15, 3721 (2003).
B. Kim and P. T. Mather, Macromolecules, 35, 8378 (2002).
K. Kim, D. Keum, and Y. Chujo, Maceomolecules, 36, 867 (2003).
C. Leu, G. M. Reddy, K. Wei, and C. Shu, Chem. Mater., 15, 2261 (2003).
J. D. Lichtenhan, N. Q. Vu, J. A. Carter, J. W. Gilman, and F. J. Feher, Macromolecules, 26, 2141 (1993).
R. A. Mantz, P. F. Jones, K. P. Chaffee, J. D. Lichtenhan, and J. W. Gilman, Chem. Mater., 8, 1250 (1996).
M. E. Wright, D. A. Schorzman, F. J. Feher, and R. Jin, Chem. Mater., 15, 264 (2003).
T. Kobayashi, T. Hayashi, and M. Tanaka, Chem. Lett., 1998, 763.
T. S. Haddad and J. D. Lichtenhan, J. Inorg. Organomet. Polym., 5, 237 (1995).
R. E. Tecklenburg, W. E. Wallace, and H. Chen, Rapid Commun. Mass Spectrom., 15, 2176 (2001).
D. P. Fasce, R. J. J. Williams, R. Erra-Balsells, Y. Ishikawa, and H. Nonami, Macromolecules, 34, 3534 (2001).
B. Dereese, P. Smet, F. Verpoort, L. Verdonck, and J. Van Beeumen, Rapid Commun. Mass Spectrom., 12, 1204 (1998).
I. E. dell’ Erba, D. P. Fasce, R. J. J. Williams, R. Erra-Balsells, Y. Fukuyama, and H. Nonami, J. Organomet. Chem., 686, 42 (2003).
D. R. Bujalski, H. Chen, R. E. Tecklenburg, E. S. Moyer, G. A. Zank, and K. Su, Macromolecules, 36, 180 (2003).
P. Eisenberg, R. Erra-Balsells, Y. Ishikawa, J. C. Lucas, A. N. Mauri, H. Nonami, C. C. Riccardi, and R. J. J. Williams, Macromolecules, 33, 1940 (2000).
J. Falkenhagen, H. Jancke, R. Krüger, E. Rikowski, and G. Schulz, Rapid Commun. Mass Spectrom., 17, 285 (2003).
R. J. J. Williams, R. Erra-Balsells, Y. Ishikawa, H. Nonami, A. N. Mauri, and C. C. Riccardi, Macromol. Chem. Phys., 202, 2425 (2001).
W. E. Wallace, C. M. Guttman, and J. M. Antonucci, J. Am. Soc. Mass Spectrom., 10, 224 (1999).
P. Eisenberg, R. Erra-Balsells, Y. Ishikawa, J. C. Lucas, H. Nonami, and R. J. J. Williams, Macromolecules, 35, 1160 (2002).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Seino, M., Kawakami, Y. Selective Vinyl Functionalization of Octakis(dimethylsiloxy)octasilsesquioxane with Allylbenzene and 1,5-Hexadiene and Copolymerization of the Products with Bis(dimethylsilyl)benzene. Polym J 36, 422–429 (2004). https://doi.org/10.1295/polymj.36.422
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.36.422