Preparation of aromatic polyamides from newly separated optically pure phenylindanedicarboxylic acid and their application to enantioseparation

Abstract

An optically pure isomer of 1,l,3.-trimethyl-3-phenylindane-4',5-dicarboxylic acid (PIDA) was obtained by introduction of racemric PIDA to a diester of the optically pure alcohol. D-(-)-pantolactone, followed by hydrolysis of the separated stereoisomer of the diester. Optically active aromatic polyamides (aramids) were synthesized by the reaction of the optically pure PIDA with various aromatic diamines. The specific rotations of these aramids ranged from + 284 to +4416. The aramids were soluble in organic solvents such as N,N-dimethylacetamide, pyridine and m-cresol. These materials had glass transition temperatures over 290 'C, and did not decompose below 380 C. The solubility and thermal behaviour were almost the same as those of the racemic aramids. The optically active aramids were examined as a stationary phase for chromatographic enantioseparation. When the aramid derived from p-phenylenediamine was used for this purpose, the stereoisomers of l-phenylethylamine could be easily separated.