| Abstract: | The synthesis of chiral side chain liquid crystalline polyacrylates with a two-stereogenic centre from L-alpha-aminoacid is described. The chiral tail is 2-chloroalcohol obtained from L-isoleucine and the spacer group has either four or eleven methylene units. The mesogenic moiety is derived from phenyl benzoate. The stereochemistry of the key intermediate (2 S ,3 S )-(+)-4- [1-(2-chloro-3-methyl)pentyloxy]phenyl benzoate ( 6 ) obtained by a Mitsunobu reaction was established by single crystal X-ray analysis. This result indicates that the nucleophilic displacement of chiral diazonium salts proceeds with overall retention of configuration. The liquid crystalline behaviour of polyacrylates P 13 and P 14 was investigated by DSC, optical microscopy, small angle X-ray scattering and depolarized light scattering. The polyacrylate P 13 , with eleven methylene units in the spacer, exhibits a chiral smectic A phase whereas the polyacrylate P 14 , with a spacer containing four methylene units, displays a chiral nematic phase. |
