K. Radley et N. Mclay, AN INVERSION IN THE CHIRALITY IN AN AMPHIPHILIC CHOLESTERIC LIQUID-CRYSTAL WHERE THE CHIRAL DOPANT IS THE CHLORIDE OF THE DECYL ESTER OF L-PROLINE, Journal of physical chemistry, 98(12), 1994, pp. 3071-3072
The chloride of the decyl ester of L-proline has been used as a chiral
dopant where the achiral host detergent was tetradecyltrimethylammoni
um bromide. The twist and the sense of the helix were measured as a fu
nction of the chiral dopant concentration, using the fingerprint textu
re and Grandjean planes observed under a polarizing microscope. The ma
gnitude of the twist as a function of the chiral dopant concentration
initially rose and fell, while the sense of helix was positive. At abo
ut 10% the twist magnitude passed through zero, and then with increasi
ng amounts of the chiral dopant the sense of the helix became negative
. This inversion in the twist sense is thought to be due to a concentr
ation-dependent distribution of the cis and trans molecular rotamers d
erived from rotation around the >CH-CO2- bond. The existence of cis an
d trans rotamers is confirmed using C-13 NMR.