Optically active helical poly(α,β-unsaturated ketone) from anionic polymerization of (S)-3-acrylyl-2,2′- bis(methoxymethoxy)-1,1′-binaphthyl

Abstract

(S)-3-acrylyl-2,2′-bis(methoxymethoxy)-1,1′-binaphthyl (3a) was synthesized and anionically polymerized using n-BuLi as an initiator. The polymer derived from 3a had a tremendous specific optical rotation [Formula: see text] = −304.2, while that of the monomer 3a is −68.7. Poly-3a was confirmed to exist in the form of a one-handed helical structure in solution by means of comparing the specific optical rotation, the circular dichroism, and UV-vis spectra with that of 3a and the model compounds such as (S)-3-propionyl-2,2′-bis(methoxymethoxy)-1,1′-binaphthyl (3b) and (S)-3-heptanoyl-2,2′-bis(methoxymethoxy)-1,1′-binaphthyl (3c). This conclusion was also confirmed by the fact that the g value of poly-3a is about 15 times of that of the monomer 3a.