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

Dokli, Irena; Ožegović, Antonija; Šimanović, Aleksandra; Hromin, Matija; Knežević, Anamarija; Višnjevac, Aleksandar; Lesac, Andreja (2022) Enantioselective Synthesis of 3-Aryl-3- hydroxypropanoic Esters as Subunits for Chiral Liquid Crystals. The Journal of Organic Chemistry, 87 (21). pp. 14045-14057. ISSN 0022-3263

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Official URL: https://pubs.acs.org/doi/10.1021/acs.joc.2c01662

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 aromatic part were obtained through asymmetric transfer hydrogenation using Ru(II) complexes in 98 - >99% ee. Chiral LC compounds of diverse topologies were further prepared without deterioration of the ee during the synthesis. 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 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 corresponding racemic forms. This paves the way for the study of self-organization and the structure-property relationship in chiral soft materials.

Item Type:

Article

Uncontrolled Keywords:

Enantioselective Synthesis ; Liquid crystals ; chiral building block

Subjects:

NATURAL SCIENCES > Chemistry > Organic Chemistry

Divisions:

Division of Organic Chemistry and Biochemistry

Projects: