Enantioselective Synthesis of 3-Aryl-3-hydroxypropanoic Esters as Subunits for Chiral Liquid Crystals.

Abstract

Chiral liquid crystals (LCs) with their unique optical and mechanical properties are perspective functional soft materials for fundamental science and advanced technological applications. Herein, we introduce the chiral 3-aryl-3-hydroxypropanoic ester moiety as a versatile building block for the preparation of LC compounds. Three chiral subunits differing in the aromatic part were obtained through asymmetric transfer hydrogenation using Ru(II) complexes with ee from 98% to >99%. Chiral LC compounds of diverse topologies were further prepared without deterioration of the ee during the synthesis. The mesomorphic behavior of rod-shaped, bent-shaped flexible dimeric, and polycatenar LCs is consistent with their topology─chiral nematic and smectic phases were identified as well as the rarely observed twist grain boundary A and blue phases. The utilization of synthetic chiral building blocks offers the possibility of fine tuning the intermolecular interactions by subtle changes in the molecular structure as well as the preparation of the corresponding racemic forms. This paves the way for the study of self-organization and the structure-property relationship in chiral soft materials.