Abstract
The subject of this review is to introduce a novel iterative methodology based on living anionic polymerization using specially designed 1,1-diphenylethylene (DPE) derivatives recently developed for the synthesis of well-defined many armed star-branched polymers with same or chemically different arm segments. The methodology basically involves only two sets of the following reaction conditions for the entire iterative synthetic sequence: (a) a linking reaction of a living anionic polymer with a DPE-chain-functionalized polymer, and (b) an in situ reaction of a DPE-functionalized agent with the anion generated by the linking reaction to reintroduce the DPE functionality usable for the next reaction. The number of arms to be linked by each stage of the iteration depends on the starting core and DPE-functionalized agents and can dramatically increase by the agent of choice. New functional asymmetric star-branched polymers involving conductive and rigid rod-like poly(acetylene) segment(s) have been synthesized by the methodology using the intermediate polymer anions produced by the linking reaction as macroinitiators to polymerize 4-methylphenyl vinyl sulfoxide, followed by thermal treatment of the resulting star-branched polymers.
Similar content being viewed by others
Article PDF
References
B. J. Bauer and L. J. Fetters, Rubber Chem. Technol., 51, 406 (1978).
S. Bywater, Adv. Polym. Sci., 30, 89 (1979).
J. Roovers, “Encyclopedia of Polymer Science and Engineering” 2nd ed., J. I. Kroschwitz, Ed., Wiley-Interscience, New York, 1985, Suppl. vol. 2, pp 478–499.
P. Rempp and J. E. Herz, “Encyclopedia of Polymer Science and Engineering” 2nd ed., J. I. Kroschwitz, Ed., Wiley-Interscience, New York, 1989, Suppl., pp 493–510.
L. J. Fetters and E. L. Thomas, “Material Science and Technology” VCH Verlangesellschaft, Weinheim, Germany, 1993, vol. 12, pp 1–31.
H. L. Hsieh and R. P. Quirk, “Anionic Polymerization: Principles and Applications” Marcel Dekker, New York, 1996, pp 333–368.
G. S. Grest, L. J. Fetters, and J. S. Huang, Adv. Chem. Phys., XCIV, 67 (1996).
P. J. Lutz and D. Rein, in “Star and Hyperbranched Polymers” M. K. Mishra and S. Kobayashi, Ed., Marcel Dekker, New York, 1999, pp 27–57.
N. Hadjichristidis, J. Polym. Sci., Part A: Polym. Chem., 37, 857 (1999).
N. Hadjichristidis, M. Pitsikalis, H. Iatrou, and C. Vlahos, Adv. Polym. Sci., 142, 72 (1999).
N. Hadjichristidis, M. Pitsikalis, S. Pispas, and H. Iatrou, Chem. Rev., 101, 3747 (2001).
N. Hadjichristidis, M. Pitsikalis, H. Iatrou, and S. Pispas, Macromol. Rapid Commun., 24, 979 (2003).
A. Hirao, M. Hayashi, Y. Tokuda, N. Haraguchi, T. Higashihara, and S.-W. Ryu, Polym. J., 34, 633 (2002).
A. Hirao, M. Hayashi, S. Lokulnant, K. Sugiyama, S.-W. Ryu, N. Haraguchi, A. Matsuo, and T. Higashihara, Prog. Polym. Sci., 30, 111 (2005).
S. T. Milner, Macromolecules, 27, 2333 (1994).
S. Okamoto, H. Hasegawa, T. Hashimoto, T. Fujimoto, H. Zhang, T. Kazama, A. Takano, and Y. Isono, Polymer, 38, 5275 (1997).
S. Sioula, N. Hadjichristidis, and E. L. Thomas, Macromolecules, 31, 5272 (1998).
N. Hadjichristidis, H. Iatrou, S. K. Behal, J. J. Chludznski, M. M. Disko, R. T. Garner, K. S. Liang, D. J. Lohse, and S. T. Milner, Macromolecules, 31, 5812 (1993).
S. Sioula, N. Hadjichristidis, and E. L. Thomas, Macromolecules, 31, 8429 (1998).
H. Hückstädt, A. Göpfert, and V. Abetz, Macromol. Chem. Phys., 201, 296 (2000).
Y. Bohbot-Raviv and Z.-G. Wang, Phys. Rev. Lett., 85, 3428 (2000).
X. He, L. Huang, and C. Pan, J. Chem. Phys., 116, 10508 (2002).
T. Gemma, A. Hatano, and T. Dotera, Macromolecules, 35, 3225 (2002).
K. Yamauchi, K. Takahashi, H. Hasegawa, H. Iatrou, N. Hadjichristidis, T. Kaneko, Y. Nishikawa, H. Jinnai, T. Matsui, H. Nishioka, M. Shimizu, and H. Furukawa, Macromolecules, 36, 6962 (2003).
X. He, L. Huang, H. Liang, and C. Pan, J. Chem. Phys., 118, 9861 (2003).
T. Lu, X. He, and H. Liang, J. Chem. Phys., 121, 9702 (2004).
T. M. Birshtein, A. A. Polotsky, and V. Abetz, Macromol. Theory Simul., 13, 512 (2004).
P. Tang, F. Qiu, H. Zhang, and Y. Yang, J. Phys. Chem. B, 108, 8434 (2004).
A. Takano, S. Wada, S. Sato, T. Araki, K. Hirahara, T. Kazama, S. Kawahara, Y. Isono, A. Ohono, N. Tanaka, and Y. Matsushita, Macromolecules, 37, 9941 (2004).
A. Takano, W. Kawashima, A. Noro, Y. Isono, N. Tanaka, T. Dotera, and Y. Matsushita, J. Polym. Sci., Part B: Polym. Phys., 43, 2427 (2005).
K. Yamauchi, S. Akasaka, H. Hasegawa, H. Iatrou, and N. Hadjichristidis, Macromolecules, 38, 8022 (2005).
Z. Li, M. A. Hillmyer, and T. P. Lodge, Macromolecules, 39, 765 (2006).
K. Hayashida, W. Kawashima, A. Takano, Y. Shinohara, Y. Amemiya, Y. Nozue, and Y. Matsushita, Macromolecules, 39, 4869 (2006).
K. Hayashida, A. Takano, S. Arai, Y. Shinohara, Y. Amemiya, and Y. Matsushita, Macromolecules, 39, 9402 (2006).
K. Hayashida, N. Saito, S. Arai, A. Takano, N. Tanaka, and Y. Matsushita, Macromolecules, 40, 3695 (2007).
N. Hadjichristidis, A. Guyot, and L. J. Fetters, Macromolecules, 11, 668 (1978).
N. Hadjichristidis and L. J. Fetters, Macromolecules, 13, 191 (1980).
J. Roovers, N. Hadjichristidis, and L. J. Fetters, Macromolecules, 16, 214 (1983).
P. M. Toporowski and J. Roovers, J. Polym. Sci., Polym. Phys. Ed., 24, 3009 (1986).
L.-L. Zhou, N. Hadjichristidis, P. M. Toporowski, and J. Roovers, Rubberr Chem. Technol., 65, 303 (1992).
J. Roovers, L.-L. Zhou, P. M. Toporowski, M. van der Zwan, H. Iatrou, and N. Hadjichristidis, Macromolecules, 26, 4324 (1993).
M. Pitsikalis, N. Hadjichristidis, G. Di Silvestro, and P. Sozzani, Macromol. Chem. Phys., 196, 2767 (1995).
J. Allgaier, K. Martin, H. J. Räder, and K. Müllen, Macromolecules, 32, 3190 (1999).
H. L. Hsieh and R. P. Quirk, “Anionic Polymerization: Principles and Applications” Marcel Dekker, New York, 1996, pp 335–347.
D. M. Knauss, H. A. Al-Muallem, T. Huang, and D. T. Wu, Macromolecules, 33, 3557 (2000).
H. Iatrou and N. Hadjichristidis, Macromolecules, 26, 2479 (1993).
T. Higashihara and Hirao, J. Polym. Sci., Part A: Polym. Chem., 42, 4535 (2004).
T. Higashihara, M. Nagura, K. Inoue, N. Haraguchi, and A. Hirao, Macromolecules, 38, 4577 (2005).
A. Mavroudis and N. Hadjichristidis, Macromolecules, 39, 535 (2006).
X. Wang, J. He, and Y. Yang, J. Polym. Sci., Part A: Polym. Chem., 45, 4818 (2007).
O. Altintas, G. Hizal, and U. Tunca, J. Polym. Sci., Part A: Polym. Chem., 46, 1218 (2008).
A. Hirao, S. Loykulnant, and T. Ishizone, Prog. Polym. Sci., 27, 1399 (2002).
A. Hirao, K. Kawasaki, and T. Higashihara, Sci. Tech. Adv. Mater., 5, 469 (2004).
A. Hirao, K. Kawasaki, and T. Higashihara, Macromolecules, 37, 5179 (2004).
Y. Zhao, T. Higashihara, K. Sugiyama, and A. Hirao, J. Am. Chem. Soc., 127, 14158 (2005).
T. Higashihara, K. Inoue, M. Nagura, and A. Hirao, Macromol. Res., 14, 287 (2006).
J. F. Douglas, J. Roovers, and K. F. Freed, Macromolecules, 23, 4168 (1990).
A. Hirao, K. Yamaguchi, K. Takenaka, K. Suzuki, S. Nakahama, and N. Yamazaki, Makromol. Chem., Rapid Commun., 3, 941 (1982).
A. Hirao, K. Kitamura, K. Takenaka, and S. Nakahama, Macromolecules, 26, 4995 (1993).
A. Hirao, M. Hayashi, and T. Higashihara, Macromol. Chem. Phys., 202, 3165 (2001).
A. Hirao and T. Higashihara, Macromolecules, 35, 7238 (2002).
A. Hirao, T. Higashihara, M. Nagura, and T. Sakurai, Macromolecules, 39, 6081 (2006).
In addition, small peaks corresponding to dimmers of the original (PSLi)s were always observed between two peaks. They may be formed by the elimination of LiH from PSLi, followed by the addition reaction of another PSLi to the resulting styryl terminus. Such a dimmer formation is usually observed by allowing PSLi to stand longer times of 24 h or more times.
J. Roovers, in “Star and Hyperbranched Polymers” M. K. Mishra and S. Kobayashi, Ed., Marcel Dekker, New York, 1999, pp 285–341.
T. Fujimoto, H. Zhang, T. Kazama, Y. Isono, H. Hasegawa, and T. Hashimoto, Polymer, 33, 2208 (1992).
H. Hückstädt, V. Abetz, and R. Stadler, Macromol. Rapid Commun., 17, 599 (1996).
S. Sioula, Y. Tselikas, and N. Hadjichristidis, Macromolecules, 30, 1518 (1997).
R. P. Quirk, T. Yoo, Y. Lee, J. Kim, and B. Lee, Adv. Polym. Sci., 153, 67 (2000).
A. Zioga, S. Sioula, and N. Hadjichristidis, Macromol. Symp., 157, 239 (2000).
S. Reutenauer, G. Hurtrez, and P. Dumas, Macromolecules, 34, 755 (2001).
M. Nasser-Eddine, S. Reutenauer, C. Delaite, G. Hurtrez, and P. Dumas, J. Polym. Sci., Part A: Polym. Chem. Ed., 42, 1745 (2004).
R. S. Kanga, T. E. Hogen-Esch, E. Randrianalimanana, A. Soum, and M. Fontanille, Macromolecules, 23, 4235 (1990).
R. S. Kanga, T. E. Hogen-Esch, E. Randrianalimanana, A. Soum, and M. Fontanille, Macromolecules, 23, 4241 (1990).
D. Reibel, R. Nuffer, and C. Mathis, Macromolecules, 25, 7090 (1992).
Y. Zhao, T. Higashihara, K. Sugiyama, and A. Hirao, Macromolecules, 40, 228 (2007).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hirao, A., Inoue, K., Higashihara, T. et al. Successive Synthesis of Well-Defined Star-Branched Polymers by Iterative Methodology Based on Living Anionic Polymerization. Polym J 40, 923–941 (2008). https://doi.org/10.1295/polymj.PJ2008064
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1295/polymj.PJ2008064
Keywords
This article is cited by
-
Precise Synthesis of Novel Ferrocene-Based Star-Branched Polymers by Using Specially Designed 1,1-Diphenylethylene Derivatives in Conjunction with Living Anionic Polymerization
Journal of Inorganic and Organometallic Polymers and Materials (2010)