Pregled bibliografske jedinice broj: 1226475
Enantioselective Synthesis of 3-Aryl-3- hydroxypropanoic Esters as Subunits for Chiral Liquid Crystals
Enantioselective Synthesis of 3-Aryl-3- hydroxypropanoic Esters as Subunits for Chiral Liquid Crystals // The Journal of Organic Chemistry, 87 (2022), 21; 14045-14057 doi:10.1021/acs.joc.2c01662 (međunarodna recenzija, članak, znanstveni)
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Naslov
Enantioselective Synthesis of 3-Aryl-3-
hydroxypropanoic Esters as Subunits for Chiral
Liquid Crystals
Autori
Dokli, Irena ; Ožegović, Antonija ; Šimanović, Aleksandra ; Hromin, Matija ; Knežević, Anamarija ; Višnjevac, Aleksandar ; Lesac, Andreja
Izvornik
The Journal of Organic Chemistry (0022-3263) 87
(2022), 21;
14045-14057
Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni
Ključne riječi
Enantioselective Synthesis ; Liquid crystals ; chiral building block
Sažetak
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.
Izvorni jezik
Engleski
Znanstvena područja
Kemija
POVEZANOST RADA
Projekti:
HRZZ-IP-2019-04-7978 - Strukturna kiralnost vs molekulska kiralnost (SMChiral) (Lesac, Andreja, HRZZ - 2019-04) ( CroRIS)
Ustanove:
Institut "Ruđer Bošković", Zagreb
Profili:
Aleksandar Višnjevac
(autor)
Andreja Lesac
(autor)
Antonija Ožegović
(autor)
Irena Dokli
(autor)
Anamarija Knežević
(autor)
Aleksandra Šimanović
(autor)
Citiraj ovu publikaciju:
Časopis indeksira:
- Current Contents Connect (CCC)
- Web of Science Core Collection (WoSCC)
- Science Citation Index Expanded (SCI-EXP)
- SCI-EXP, SSCI i/ili A&HCI
- Scopus
- MEDLINE