Abstract
According to the molecular design, a main chain-type polyrotaxane (B) was synthesized by the initial threading of sec-ammonium axle 5 into poly(crown ether) 3 to polypseudorotaxane 7 followed by end-capping of the axle terminal with a bulky aromatic isocyanate. The pseudorotaxane formation using poly(crown ether) 3 was studied in detail from viewpoints of effects of solvent, temperature, concentration, feed ratio, and so on. The complete pseudorotaxanation (>99%) was achieved, while the incorporation ratio of the axle moiety was finely controllable, by changing the feed ratio of 3 and 5. The corresponding polyrotaxane 8 was obtained in a high yield and in a high rotaxanated ratio by the end-capping of 7 with 3,5-dimethylphenyl isocyanate. N-Acetylation of 8 with acetic anhydride afforded neutral polyrotaxane 9 of which molecular weights could be estimated by GPC. Polypseudorotaxane 7 was utilized for the preparation of a new type of polyrotaxane network: the reaction of 7 with 4,4′-methylenebis(phenyl isocyanate) (MDI) which combined terminal OH group of the axle of 7 yielded a gelled materials 10. The gel was swollen in polar solvents such as dimethyl sulfoxide (DMSO, 9800%) to give transparent material. 1H NMR spectrum of 10 indicated the formation of the rotaxane structure as crosslinking point, although the degree of crosslink was low.
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References
A. Harada, J. Li, and M. Kamachi, Nature, 356, 325 (1992).
A. Harada, J. Li, and M. Kamachi, J. Am. Chem. Soc., 116, 3192 (1994).
“Molecular Catenanes, Rotaxanes and Knots,” J. P. Sauvage and C. Dietrich-Buchecker, Ed., Willy-VCH, Weinheim, 1999, p 277.
F. M. Raymo and J. F. Stoddart, “Supramolecular Polymers,” A. Cifferi, Ed., Marcel Dekker, 2000, p 323.
T. Takata, N. Kihara, and Y. Furusho, Adv. Polym. Sci., 171, 1 (2004).
F. Huang and H. W. Gibson, Prog. Polym. Sci., 30, 982 (2005).
F. Huang and H. W. Gibson, Prog. Polym. Sci., 30, 982 (2005).
G. Wenz, B. Han, and A. Müller, Chem. Rev., 106, 782 (2006).
T. Takata, Polym. J., 38, 1 (2006).
C. Gong, T. E. Glass, and H. W. Gibson, Macromolecules, 31, 308 (1998).
K. Nagapudi, J. Hunt, C. Shepherd, J. Baker, and H. W. Beckham, Macromol. Chem. Phys., 200, 2541 (1999).
H. W. Gibson, P. T. Engen, and S. Lee, Polymer, 40, 1823 (1999).
I. Yamaguchi, K. Miya, K. Osakada, and T. Yamamoto, Polym. Bull., 44, 247 (2000).
N. Kihara, K. Hinoue, and T. Takata, Macromolecules, 38, 223 (2005).
X. Wang, H. Kim, Y. Fujita, A. Sudo, H. Nishida, and T. Endo, Macromolecules, 39, 1046 (2006).
R. Liu, A. Harada, and T. Takata, Polym. J., 39, 21 (2007).
R. Liu, N. Kihara, A. Harada, and T. Takata, J. Polym. Sci., Polym. Chem., 45, 1571 (2007).
H. Hirose, H. Sano, G. Mizutani, M. Eguchi, T. Ooya, and N. Yui, Polym. J., 30, 1093 (2006).
J. Jeromin and H. Ritter, Macromolecules, 32, 5236 (1999).
T. Takata, H. Kawasaki, S. Asai, N. Kihara, and Y. Furusho, Chem. Lett., 111 (1999).
I. Yamaguchi, K. Osakada, and T. Yamamoto, Macromolecules, 33, 2315 (2000).
I. Yamaguchi, K. Osakada, and T. Yamamoto, Macromolecules, 33, 2315 (2000).
T. Takata, H. Kawasaki, N. Kihara, and Y. Furusho, Macromolecures, 34, 5499 (2001).
T. Oku, Y. Furusho, and T. Takata, J. Polym. Sci. Polym. Chemm., 41, 119 (2003).
Y. Sohgawa, H. Fujimori, Y. Furusho, N. Kihara, and T. Takata, Chem. Lett., 774 (2001).
J. Cantrill, G. J. Youn, and J. F. Stoddart, J. Org. Chem., 66, 6857 (2001).
T. Arai and T. Takata, Chem. Lett., 36, 418 (2007).
M. Kidowaki, C. Zhao, T. Kataoka, and K. Ito, Chem. Commun., 4102 (2006).
T. Kataoka, M. Kidowaki, C. Zhao, H. Minamikawa, T. Shimizu, and K. Ito, J. Phys. Chem. B, 110, 24377 (2006).
Y. Okumura and K. Ito, Adv, Mater., 13, 485 (2001).
K. Ito, Polym. J., 39, 489 (2007).
T. Karino, Y. Okuyama, K. Ito, and M. Shibayama, Macromolecules, 37, 6177 (2004).
T. Karino, Y. Okumura, C. Zhao, T. Kataoka, K. Ito, and M. Shibayama, Macromolecules, 38, 6161 (2005).
C. Zhao, Y. Domon, Y. Okuyama, S. Okabe, M. Shibayama, and K. Ito, J. Phys: Condes. Matter, 17, s2841 (2005).
C. Gong and H. W. Gibson, Angew. Chem., Int. Ed., 37, 310 (1998).
C. Gong and H. W. Gibson, J. Am. Chem. Soc., 119, 8585 (1997).
T. Oku, Y. Furusho, and T. Takata, Angew. Chem., Int. Ed., 43, 966 (2004).
T. Takata and H. Otsuka, Yuki Gosei Kagaku Kyoukaishi (J. Syn. Org. Chem., Jpn.), 64, 194 (2006).
T. Takata, Y. Kohsaka, and G. Konishi, Chem. Lett., 36, 292 (2007).
Y. Furusho, H. Sasabe, D. Natsui, K. Murakawa, T. Takata, and T. Harada, Bull. Chem. Soc. Jpn., 77, 179 (2004).
Y. Tachibana, N. Kihara, and T. Takata, J. Am. Chem. Soc., 126, 3438 (2004).
N. Kihara and T. Takata, Yuki Gosei Kagaku Kyoukaishi (J. Syn. Org. Chem., Jpn.), 59, 206 (2001).
Similar figure to Figure 3 has already been reported in the previous paper. 17 Since the quality of the spectra (iii) and (v) had not been sufficiently high, we again showed these spectra in the present Figure 3 to contribute to easy understanding.
H. Kawasaki, N. Kihara, and T. Takata, Chem. Lett., 28, 1015 (1999).
Y. Furusho, T. Oku, T. Hasegawa, A. Tsuboi, N. Kihara, and T. Takata, Chem. Eur. J., 9, 2895 (2003).
Y. Tachibana, H. Kawasaki, N. Kihara, and T. Takata, J. Org. Chem., 71, 5093 (2006).
T. Endo, T. Suzuki, F. Sanda, and T. Takata, Macromolecules, 29, 3315 (1996).
H. K. Kim, X. S. Wang, Y. Fujita, A. Sudo, H. Nishida, M. Fujii, and T. Endo, Macromol. Rapid Commun., 26, 1032 (2005).
H. J. Kwon, Y. Osada, and J. P. Gong, Polym. J., 38, 1211 (2006).
H. Okamura, K. Shin, and M. Shirai, Polym. J., 38, 1237 (2006).
T. Kimura, Y. Nakamoto, and G. Konishi, Polym. J., 38, 606 (2006).
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Kohsaka, Y., Konishi, Gi. & Takata, T. Synthesis of A Main Chain-Type Polyrotaxane Consisting of Poly(crown ether) and sec-Ammonium Salt Axle and Its Application to Polyrotaxane Network. Polym J 39, 861–873 (2007). https://doi.org/10.1295/polymj.PJ2007030
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DOI: https://doi.org/10.1295/polymj.PJ2007030
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