Optically active helical vinyl polymers via helix-sense-selective anionic polymerization of (S)-3-vinyl-2,2′-bis(methoxymethoxy)-1,1′-binaphthyl

A novel vinyl monomer, (S)-3-vinyl-2,2′-bis(methoxymethoxy)-1,1′-binaphthyl 2, was synthesized and underwent helix-sense-selective anionic polymerization to obtain helical polymers with an excess screw sense. The polymer ( [ α ] 365 25  = −1610.0°) exhibited optical rotation as large as fourfold that of the monomer ( [ α ] 365 25  = −356.0°). Poly-2 was confirmed to keep a prevailing helicity of backbone in solution by means of comparing the specific optical rotation, the CD and UV–vis spectra with that of monomer 2 and the model compound such as (S)-3-ethyl-2,2′-bis(methoxymethoxy)-1,1′-binaphthyl 3. The helical conformation of poly-2 was stable and insensitive to temperature variation. The excess value of one-handed helicity of poly-2 decreased with the increase of polymerization temperature.