Abstract
Asymmetric polymerization of acrylic monomers and an isocyanate derivative leading to a helical conformation is described. 1-Phenyldibenzosuberyl methacrylate, triphenylmethyl acrylate, and N,N-diphenylacrylamide were polymerized using the complexes of diphenylethylenediamine monolithium amide with (-)-sparteine, (S,S)-(+)-2,3-dimethoxy-1,4-bis(dimethylamino)butane, and (S)-(+)-1-(2-pyrrolidinylmethyl)pyrrolidine. The methacrylate gave a purely one-handed helical, optically active polymer ([α]365 +1670° ~ +1780°) having a perfect isotactic structure; the polymer exhibited chiral recognition ability to some racemic compounds. This monomer gave optically active polymers also by radical mechanism. The acrylate also gave an optically active, helical polymer ([α]365 +102°) having a dyad isotacticity of 70% using the pyrrolidine complex. The poly(methyl acrylate) derived from the polyacrylate showed a specific rotation which appears to be based on configurational chirality of the main chain. The acrylamide gave an optically active polymer ([α]365-429°) which may have a helical structure by asymmetric anionic polymerization; the polymer had a dyad isotacticity of 86%. m-Methylphenyl isocyanate was polymerized using optically active lithium alkoxides and amides to produce a polymer having a chiral group at the α-end. A prevailing one-handed helical structure was induced for the main chain due to the chiral end group.
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© 1996 Springer-Verlag Berlin Heidelberg
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Okamoto, Y., Nakano, T., Habaue, S. (1996). Helical Polymers: Synthesis, Conformation, and Function. In: Kamachi, M., Nakamura, A. (eds) New Macromolecular Architecture and Functions. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-80289-8_10
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DOI: https://doi.org/10.1007/978-3-642-80289-8_10
Publisher Name: Springer, Berlin, Heidelberg
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