Synthesis and characteristics of chiral polymers with camphanediol moieties

Optically active exo,exo-2,3-camphanediol (CPO) was synthesized from (+)-camphor. The chiral polymers poly(CPO-co-TDI) and poly(CPO-co-IPDI) were synthesized by step polymerization of chiral compound CPO with toluene-2,4-diisocyanate (TDI) and isophorone diisocyanate (IPDI). Effects of solvents, reaction time and temperature on the polymerization were investigated. To investigate the stereo structure of the chiral polymers, two kinds of model compounds, exo,exo-2,3-bornylene N,N'-diphenyldicarbamate and exo,exo-2,3-bornylene N,N'-dipropyldicarbamate, related to the prepared polymers were synthesized. Chiroptical characteristics and stereo structures of the chiral polymers were investigated by using a circular dichroic spectrometer. Effects of temperature and solvents on the specific rotation of the chiral polymers were evaluated. The results obtained in this investigation suggest that the synthesized chiral polymers have no one-handed helix conformation.