SYNTHESIS AND CHIROPTICAL PROPERTIES OF OPTICALLY-ACTIVE POLYAMIDES HAVING ANTI HEAD-TO-HEAD UMBELLIFERONE DIMER AS A COMPONENT

Optically active polyamides having 2,4-dihydroxyphenyl groups in the side chain were synthesized by the ring-opening polyaddition reaction of (-)-anti head-to-head umbelliferone dimer with diamines, such as 1, 6-hexanediamine, 1,4-phenylenediamine, m-xylene-alpha,alpha'-diamine, and piperazine. Chiroptical properties of the polyamides were elucidated on the basis of their circular dichroism (CD) spectra in solution and in the film state. The polyamide having a 1,4-phenylene moiety in the diamine component existed in an ordered conformation even in a neutral DMAc solution. Moreover, the polyamides having 1,4-phenylenediamine or piperazine as a component existed in an ordered conformation in the film state. The steric repulsion and/or hydrogen bonding of the para-hydroxyl group on the phenyl group in the side chain was found to play a significant role to reveal the ordered conformations.