501
Views
0
CrossRef citations to date
0
Altmetric
Research Article

Oxazoline derivatives exhibiting chiral liquid crystalline mesophases

ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon show all
Pages 2360-2370 | Received 22 May 2023, Accepted 23 Aug 2023, Published online: 03 Sep 2023

References

  • Goodby JWG, editor. Ferroelectric liquid crystals: principles, properties, and applications. Philadelphia: Gordon and Breach Science Publishers; 1991.
  • Kitzerow H-S, Bahr C, editors. Chirality in liquid crystals. New York: Springer; 2001. doi: 10.1007/b97374
  • Wu S, Hsu H. Synthesis and mesomorphic properties of fluoro‐substituted chiral liquid crystals derived from (S)‐lactic acid with alkoxyethanols. Liq Cryst. 2007;34:1159–1165. doi: 10.1080/02678290701663845
  • Wu S‐L, Lai F‐S. Synthesis and ferroelectric properties of new chiral liquid crystals derived from (S)‐lactic acid with alkoxyethanols. Liq Cryst. 2005;32:1243–1249. doi: 10.1080/02678290500139799
  • Brombach F, Neudörfl JM, Blunk D. The chiral pool as valuable natural source: new chiral mesogens made from lactic acid. Mol Cryst Liq Cryst. 2011;542(1):62/[584]–74/[596]. doi: 10.1080/15421406.2011.569689
  • Ocak H, Canli NY, Eran BB. Synthesis, mesomorphic and dielectric properties of new bent-core liquid crystal with a terminal lactate group. J Mol Liquids. 2021;1223:128975. doi: 10.1016/j.molstruc.2020.128975
  • Wang F, Liu W, Li Y, et al. A “core determination” phenomenon in four dichiral liquid crystals containing two lactate groups. Mol Cryst Liq Cryst. 2023;756(1):1–10. doi: 10.1080/15421406.2022.2112494
  • Wu X, Wu L, Guo Y, et al. Chirality driven mesomorphic behaviour difference: dichiral compounds containing two lactate groups. Liq Cryst. 2020;47(4):471–476. doi: 10.1080/02678292.2019.1672820
  • Senthil S, Srividhya D, Manjunathan S, et al. Synthesis and mesomorphic properties of chiral liquid crystal dimers containing lactate units. J Mol Struct. 2008;877(1–3):50–55. doi: 10.1016/j.molstruc.2007.07.022
  • Kašpar M, Bílková P, Bubnov A, et al. New chlorine‐substituted liquid crystals possessing frustrated TGB a and SmQ phases. Liq Cryst. 2008;35(5):641–651. doi: 10.1080/02678290802056212
  • Novotná V, Kašpar M, Hamplová V, et al. Synthesis and mesomorphic properties of new compounds exhibiting TGBA and TGBC liquid crystalline phases. Liq Cryst. 2008;35(3):287–298. doi: 10.1080/02678290701862215
  • Novotná V, Kašpar M, Hamplová V, et al. Ferroelectric, antiferroelectric and TGB phases in lactic acid derivatives. Liq Cryst. 2012;39(4):477–486. doi: 10.1080/02678292.2011.653411
  • Podoliak N, Novotná V, Kašpar M, et al. Anomalous phase sequence in new chiral liquid crystalline materials. Liq Cryst. 2014;41(2):176–183. doi: 10.1080/02678292.2013.846424
  • Novotná V, Stulov S, Hamplová V, et al. The cholesteric and TGB phases under the applied electric field. Liq Cryst. 2021;48(9):1283–1294. doi: 10.1080/02678292.2020.1858513
  • Novotná V, Hamplová V, Glogarová M, et al. Effect of the applied electric field on new cholesterics with extremely short pitch. Liq Cryst. 2018;45(4):634–640. doi: 10.1080/02678292.2017.1376126
  • Smekhova A, Novotná V, Fekete L, et al. Ultra-short helix pitch and spiral ordering in cholesteric liquid crystal revealed by resonant soft X-ray scattering. Soft Matter. 2022;18(1):89–96. doi: 10.1039/D1SM01543E
  • Hamplová V, Novotná V, Kašpar M. Lactic acid derivatives with three-phenyl ring molecular core: design and mesomorphic properties. Ferroelectrics. 2014;468(1):18–27. doi: 10.1080/00150193.2014.932655
  • Podoliak N, Novotná V, Hamplová V, et al. Structural optimisation of lactic acid derivatives to obtain enhanced ferroelectric properties in smectic phases. Liq Cryst. 2023;50(1):149–156. doi: 10.1080/02678292.2022.2131917
  • Vojtylová T, Kašpar M, Hamplová V, et al. Chiral HPLC for a study of the optical purity of new liquid crystalline materials derived from lactic acid. Phase Transit. 2014;87(8):758–769. doi: 10.1080/01411594.2014.893344
  • Kuball H-G, Brüning H, Müller T, et al. Helical twisting power of chiral mono- and bis-aminoanthraquinones. Intramolecular and intermolecular chirality transfer in liquid-crystal phases. J Mater Chem. 1995;5(12):2167–2174. doi: 10.1039/JM9950502167
  • Kuball H-G, Brüning H. Helical twisting power and circular dichroism as chirality observations: The intramolecular and intermolecular chirality transfer. Chirality. 1997;9:407–423. doi: 10.1002/(SICI)1520-636X(1997)9:5/6<407:AID-CHIR3>3.0.CO;2-2
  • Kelly S, Buchecker R, inventors; F. Hoffmann-La Roche AG, assignee. Chiral oxazolines as dopants for liquid crystals mixtures. European Patent EP0534258. 1993 Mar 31.
  • Shoshi M, inventor; Ricoh Company, Ltd., assignee. Optically active oxazoline compounds, liquid crystal composition containing the same and optical switching method using the same. United States patent US-5159084-A. 1992 Oct 27.
  • Serrano JL, Sierra T, Gonzalez Y, et al. Improving FLC properties. Simplicity, planarity, and rigidity in new chiral oxazoline derivatives. J Am Chem Soc. 1995;117(32):8312–8321. doi: 10.1021/ja00137a003
  • Maiti M, Gao L-J, Huang C, et al. Bifunctional aryloxyphosphoramidate prodrugs of 2′-C-Me uridine: synthesis and anti-HCV activity. Org Biomol Chem. 2016;14:8743–8757. doi: 10.1039/C6OB01189F
  • Li L-B, Dan W-J, Tan F-F, et al. Synthesis and antibacterial activities of yanglingmycin analogues. Chem Pharm Bull. 2015;63(1):33–37. doi: 10.1248/cpb.c14-00578
  • Pomeisl K, Vaňkátová P, Hamplová V. Enantioselective high‐performance liquid chromatography of aryl‐substituted oxazolines as an efficient tool for determination of chiral purity of serine medicinal components. J Sep Sci. 2022;45(13):2217–2227. doi: 10.1002/jssc.202100958
  • Vaňkátová P, Folprechtová D, Kalíková K, et al. Enantiorecognition ability of different chiral selectors for separation of liquid crystals in supercritical fluid chromatography; critical evaluation. J Chromatogr A. 2020;1622:461138. doi: 10.1016/j.chroma.2020.461138
  • Vaňkátová P, Kubíčková A, Kalíková K. Enantioseparation of liquid crystals and their utilization as enantiodiscrimination materials. J Chromatogr A. 2022;1673:463074. doi: 10.1016/j.chroma.2022.463074
  • Firefly version 8 [Internet]. Moscow: Granovsky AA; [cited 2023 May 17]. Available from: http://classic.chem.msu.su/gran/firefly/index.html
  • Schmidt MW, Baldridge KK, Boatz JA, et al. General atomic and molecular electronic structure system. J Comput Chem. 1993;14(11):1347–1363. doi: 10.1002/jcc.540141112