SYNTHESIS AND OPTICAL-PROPERTIES OF ASYMMETRIC POLYAMIDES DERIVED FROM CYCLOPROPYL DIACIDS AND DIAMINES

In the reported experiments, the asymmetric polyamides were prepared from the dicarbonyl chloride of ( plus ) (S)- or ( minus ) (R)-trans-1,2-cyclopropanedicarboxylic acid (C3A) with either the dihydrochloride salt of ( plus ) (S)- or ( minus ) (R)-trans-1,2-diaminocyclopropane (C3B) or the dihydrobromide salt of ( plus ) (S)- or ( minus ) (R)-trans-1,2-bis(methylamino)cyclopropane (C3MB) by interfacial polycondensation. Several diamide model compounds composed of these monomers were also synthesized. Polyamides obtained were characterized by spectroscopy, viscosity measurement and optical properties determination. The polyamides and diamides derived from enantiomers exhibit mirror image spectra. Poly( plus )C3A( plus )C3B and poly( plus )C3A( plus )C3MB in every solvent studied exhibit a marked enhancement of the rotatory strength of ORD and CD with respect to the corresponding diamide models.