Abstract
1-(3-Pyridyl)dibenzosuberyl methacrylate was synthesized and polymerized using the complexes of N,N′-diphenylethylenediamine monolithium amide with (+)-1-(2-pyrrolidinylmethyl)pyrrolidine, (+)-2,3-dimethoxy-1,4-bis(dimethylamino)butane, and (−)-sparteine in toluene at −78°C. The polymers obtained by the helix-sense-selective anionic polymerization were highly isotactic and exhibited large dextrorotation based on single-handed helical conformation. Free-radical polymerization in toluene with (iso-PrOCOO)2 at 40°C and with α,α′-azobisisobutyronitrile at 60°C gave nearly perfectly isotactic polymers. The optically active polymer exhibited chiral recognition ability toward trans-stilbene oxide and Tröger’s base as revealed by chiral adsorption experiments.
Similar content being viewed by others
Article PDF
References
Y. Okamoto, K. Suzuki, K. Ohta, K. Hatada, and H. Yuki, J. Am. Chem. Soc., 101, 4763 (1979).
T. Nakano, Y. Okamoto, and K. Hatada, J. Am. Chem. Soc., 114, 1318 (1992).
Y. Okamoto, H. Mohri, and K. Hatada, Chem. Lett., 1879 (1988).
Y. Okarnoto, H. Mohri, T. Nakano, and K. Hatada, Chirality, 3, 277 (1991).
Y. Okamoto and T. Nakano, Chem. Rev., 94, 349 (1994).
T. Nakano and Y. Okamoto, in “Catalysis in Precision Polymerization,” S. Kobayashi, Ed., Wiley, New York, N.Y., 1997, pp 293–309.
Y. Okamoto, CHEMTECH, 1987, 144.
Y. Okamoto and K. Hatada, J. Liq. Chromatogr., 9, 369 (1986).
T. Nakano, M. Mori, and Y. Okamoto, Macromolecules, 26, 867 (1993).
T. Nakano, A. Matsuda, M. Mori, and Y. Okamoto, Polym. J., 28, 330 (1996).
T. Nakano, Y. Shikisai, and Y. Okamoto, Polym. J., 28, 51 (1996).
T. Nakano, A. Matsuda, and Y. Okamoto, Polym. J., 28, 556 (1996).
T. Nakano, K. Taniguchi, and Y. Okamoto, Polym. J., 29, 540 (1997).
Y. Okamoto, H. Mohri, and K. Hatada, Polym. J., 21, 439 (1989).
T. Nakano, A. Matsuda, and Y. Okamoto, manuscript in preparation.
Y. Okamoto, H. Mohri, T. Nakano, and K. Hatada, J. Am. Chem. Soc., 111, 5952 (1989).
Sample concentration was originally determined based on the sample volume at room temp 25°C but the concentration at 60°C has been corrected using a calculated volume increment of chloroform (4.8 %) with respect to the volume at 25°C. For the method of calculation, see: “Landolt Börnstein Zahlenwerte und Funktionen aus Physik, Chemie, Astronomie, Geophysik und Technik,” 6 Aufl., II Band, 1 Teil, Springer Verlag, 1971, S. 378–718.
Y. Okamoto, T. Nakano, Y. Shikisai, and M. Mori, Makromol. Chem. Symp., 89, 479 (1995).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nakano, T., Satoh, Y. & Okamoto, Y. Asymmetric Polymerization of 1-(3-Pyridyl)dibenzosuberyl Methacrylate and Chiral Recognition by the Obtained Optically Active Polymer Having Single-Handed Helical Conformation. Polym J 30, 635–640 (1998). https://doi.org/10.1295/polymj.30.635
Issue Date:
DOI: https://doi.org/10.1295/polymj.30.635