hrvatski jezikClear Cookie - decide language by browser settings

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

[img] PDF - Accepted Version - article
Download (1MB)


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
Project titleProject leaderProject codeProject type
Strukturna kiralnost vs molekulska kiralnost-SMChiralAndreja LesacIP-2019-04-7978HRZZ
Depositing User: Irena Dokli
Date Deposited: 15 Feb 2024 13:47
DOI: 10.1021/acs.joc.2c01662

Actions (login required)

View Item View Item


Downloads per month over past year

Increase Font
Decrease Font
Dyslexic Font