Abstract
Asymmetric anionic polymerization of 1-phenyldibenzosuberyl acrylate (PDBSA) was performed in toluene using complexes of N,N′-diphenylethylenediamine monolithium amide (DPEDA-Li) or 9-fluorenyllithium with chiral ligands, (+)-(S)-1-(2-pyrrolidinylmethyl)pyrrolidine, (−)-(S)-1,2-bis(2-methoxymethylpyrrolidin-1-yl)ethane, (−)-sparteine, and (+)-(2S,3S)-2,3-dimethoxy-1,4-bis(dimethylamino)butane ((+)-DDB). The (+)-DDB-DPEDA-Li system afforded 25 the polymer of the highest specific rotation ([α]36525=−129° in CHCl3) and isotacticity (m=0.62). Optical rotation of the polymerization system with the (+)-DDB-DPEDA-Li complex at −78°C increased with time. The CD spectral pattern of the polymer was quite similar to that of the one-handed helical, optically active poly(triphenylmethyl methacrylate) (PTrMA). These results suggest that optical activity may be attributed to chiral conformation of the polymer chain produced through polymerization.
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Tanaka, T., Habaue, S. & Okamoto, Y. Asymmetric Anionic Polymerization of 1-Phenyldibenzosuberyl Acrylate Affording Optically Active Polymer with Helical Conformation. Polym J 27, 1202–1207 (1995). https://doi.org/10.1295/polymj.27.1202
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DOI: https://doi.org/10.1295/polymj.27.1202