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Pregled bibliografske jedinice broj: 1226475

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
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

Poveznice na cjeloviti tekst rada:

doi pubs.acs.org

Citiraj ovu publikaciju:

Dokli, Irena; Ožegović, Antonija; Šimanović, Aleksandra; Hromin, Matija; Knežević, Anamarija; Višnjevac, Aleksandar; Lesac, Andreja
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)
Dokli, I., Ožegović, A., Šimanović, A., Hromin, M., Knežević, A., Višnjevac, A. & Lesac, A. (2022) Enantioselective Synthesis of 3-Aryl-3- hydroxypropanoic Esters as Subunits for Chiral Liquid Crystals. The Journal of Organic Chemistry, 87 (21), 14045-14057 doi:10.1021/acs.joc.2c01662.
@article{article, author = {Dokli, Irena and O\v{z}egovi\'{c}, Antonija and \v{S}imanovi\'{c}, Aleksandra and Hromin, Matija and Kne\v{z}evi\'{c}, Anamarija and Vi\v{s}njevac, Aleksandar and Lesac, Andreja}, year = {2022}, pages = {14045-14057}, DOI = {10.1021/acs.joc.2c01662}, keywords = {Enantioselective Synthesis, Liquid crystals, chiral building block}, journal = {The Journal of Organic Chemistry}, doi = {10.1021/acs.joc.2c01662}, volume = {87}, number = {21}, issn = {0022-3263}, title = {Enantioselective Synthesis of 3-Aryl-3- hydroxypropanoic Esters as Subunits for Chiral Liquid Crystals}, keyword = {Enantioselective Synthesis, Liquid crystals, chiral building block} }
@article{article, author = {Dokli, Irena and O\v{z}egovi\'{c}, Antonija and \v{S}imanovi\'{c}, Aleksandra and Hromin, Matija and Kne\v{z}evi\'{c}, Anamarija and Vi\v{s}njevac, Aleksandar and Lesac, Andreja}, year = {2022}, pages = {14045-14057}, DOI = {10.1021/acs.joc.2c01662}, keywords = {Enantioselective Synthesis, Liquid crystals, chiral building block}, journal = {The Journal of Organic Chemistry}, doi = {10.1021/acs.joc.2c01662}, volume = {87}, number = {21}, issn = {0022-3263}, title = {Enantioselective Synthesis of 3-Aryl-3- hydroxypropanoic Esters as Subunits for Chiral Liquid Crystals}, keyword = {Enantioselective Synthesis, Liquid crystals, chiral building block} }

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


Citati:





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