Optical Activity of Homochiral Polyamides in Solution and Solid State: Structural Function for Chiral Induction.

Abstract

In this work, we have explored a simple and facile approach to prepare optically active helical polyamides. The hydroxyl groups of l-TA and d-TA were protected by O-alkoyl ester, and the resulting enantiomers, l-2,3-di-O-acetyl-tartaric acid (l-ATA) and d-2,3-di-O-acetyl-tartaric acid (d-ATA) crystals, were obtained. A pair of aliphatic homochiral polyamides of PA-l and PA-d are prepared using l-ATA, d-ATA, and achiral 1,11-undecanediamine as building blocks via interfacial polycondensation. PA-l and PA-d display negative and positive mirror circular dichroism (CD) spectra images in both solution and solid state. Moreover, the polyamides in solid state display different CD signals and stronger optical activity compared to those in ethanol and even the related chiral monomers in solid state, which was due to the helical conformation of the polyamides in solid state. Scanning electron microscopy results indicated that the aggregations of PA-l express left-handed helical sense, whereas those of PA-d express right-handed helix. In addition, the induced CD signals from the chiral conformation of the backbone become weaker when increasing the temperature from 0 to 60 °C in dilute solution. Either of the polyamides displays relatively stable CD images in solid state when elevating the temperature from 0 to 90 °C.