ХИРАЛЬНЫЙ БИС(КАМФОРОЛИДЕН)ЭТИЛЕНДИАМИН КАК ИНДУКТОР СПИРАЛЬНОЙ МЕЗОФАЗЫ В СМЕСИ АЛКОКСИЦИАНОБИФЕНИЛОВ
Аннотация
Исследованы мезоморфные, оптические и диэлектрические свойства нематиче-ской смеси 4-пентилокси и 4-гептилокси-4'-цианобифенилов допированной оптически ак-тивным бис(камфоролиден)этилендиамином. Методом поляризационной микроскопии измерены температуры просветления смесей. Проведена оценка степени дестабилизации мезофазы при введении допанта. Измерен шаг спирали индуцированной хиральной нема-тики в смесях. Изучено влияние хирального допанта на анизотропные характеристики мезофазы.
Литература
Money T. Camphor: A Chiral Starting Material in Natural Product Synthesis. Nat. Prod. Rep. 1985. V. 2. P. 253289.
Anjaneyulu B., Sangeeta, Saini N. A Study on Camphor Deriva-tives and Its Applications. 2021. V. 25(12). P.1404–1428. DOI: 10.2174/1385272825666210608115750.
Sokolova A.S., Yarovaya O.I., Shernyukov A.V., Pokrovsky M.A., Pokrovsky A.G., Lavrinenko V.A., Zarubaev V.V., Tre-tiak T.S., Anfimov P.M., Kiselev, O.I. New quaternary ammo-nium camphor derivatives and their antiviral activity, geno-toxic effects and cytotoxicity. Bioorg. Med. Chem. 2013. 21. P. 6690–6698. DOI: 10.1016/j.bmc.2013.08.014.
Caselli A., Giovenzana G.B., Palmisano G., Sistic M., Pilati T. Synthesis of C2-symmetrical diamine based on (1R)-(+)-camphor and application to oxidative aryl coupling of naph-thols Tetrahedron: Asymmetry. 2003. V. 14. P. 1451–1454. DOI: 10.1016/S0957-4166(03)00221-0.
Burmistrov V.A., Novikov I.V., Aleksandriiskii V.V. Appear-ance of induced chiral nematic phase in solutions of 4-n-al-kyloxy-4‘- cyanobyphenyles with symmetric camphorsubsti-tuted hemiporphyrazines. J. Mol. Liq. 2019. V. 287. P. 110961. DOI: 10.1016/j.molliq.2019.110961.
Burmistrov V.A., Novikov I.V., Aleksandriiskii V.V. Intermo-lecular interactions and chiral induction in nematic liquid crystal phase by camphorsubstituted 2,3-dicyanopyrazine. J. Mol. Liq. 2017. 244. P. 398404. DOI: 10.1016/j.mol-liq.2017.08.124.
Kelly S.M., O’Neill M. Liquid Crystals for Electro-Optic Ap-plications. Handbook of Advanced Electronic and Photonic Materials and Devices / Ed. by H.S. Nalwa. N.Y. etc.: Aca-demic Press, 2000. 7. P. 1–66.
Onuchak L.A., Arutunov J.I., Kuraeva J.G., et.al Russian pa-tent RU 2528126. Method for analysis of structural and opti-cal isomers. 10.09. 2014.
Matt B., Pondman K.M., Asshoff S.J., ten Haken B., Fleury B., Katsonis N. Soft Magnets from the Self-Organization of Magnetic Nanoparticles in Twisted Liquid Crystals. An-gew. Chem. Int. Ed. 2014. 53. P. 12446–12450. DOI: 10.1002/anie.201404312.
Eelkema R. Photo-responsive doped cholesteric liquid crystals. Liq. Cryst. 2011. 38. P. 1641–1652. DOI: 10.1080/02678292.2011.600779
Popov N., Honaker L.W., Popova M., Usol’tseva N., Mann E.K., Jákli A., Popov P. Thermotropic Liquid Crystal-As-sisted Chemical and Biological Sensors. Materials. 2018. 11. P. 20. DOI: 10.3390/ma11010020.
Yoshizawa A. Nanostructured assemblies of liquid-crystalline supermolecules: from display to medicine. Liq. Cryst. 2019. 46. P. 19501972. DOI: 10.1080/02678292.2019.1611966.
Ferrarini A., Pieraccini S., Masiero S., Spada G.P. Chiral amplification in a cyanobiphenyl nematic liquid crystal doped with helicene-like derivatives. Beilstein J. of Org. Chem. 2009. 5. (50). P. 1–8. DOI: 10.3762/bjoc.5.50.
Burmistrov V.A., Aleksandriiskii V.V., Novikov I.V., Koifman O.I. Mechanisms of chiral transfer in optically active dopant – nematic liquid crystal systems. Жидк. крист. и их практич. ис-польз. / Liq. Cryst. and their Appl. 2020. 20 (4). P. 6–26. DOI: 10.18083/LCAppl.2020.4.6.
Burmistrov V.A., Novikov I.V., Aleksandriiskii V.V., Belykh D.V., Startseva O.M., Koifman O.I. Chirality transfer from chlorin e6 13(N)-methylamide-15,17-dimethyl ester and its nickel complex to nematic liquid crystals. Journal of Molec-ular Liquids. 2022. 347. P118330. DOI: 10.1016/j.mol-liq.2021.118330.
Sokolova A.S., Yarovaya O.I., Korchagina D.V., Zarubaev V.V., Tretiak T.S., Anfimov P.M., Kiselev O.I., Salakhutdinov N.F. Camphor-based symmetric diimines as inhibitors of influenza virus reproduction. Bioorganic & Medicinal Chemistry. 2014. 22. P. 2141–2148. DOI: 10.1016/j.bmc.2014.02.038.
Raza Z., Đaković S., Vinković V., Šunjić V. Structural Properties of Some C2-Symmetric Schiff Bases and Stereoselectivity in Cyclopropanation of Styrene by Their Cu(I) Complexes Croatica Chemica Acta. 1996. V. 69. N 4. P. 15451559. https://hrcak.srce.hr/135990.
Pieraccini S., Ferrarini A., Spada G.P. Chiral Doping of Ne-matic Phases and Its Application to the Determination of Ab-solute Configuration. Chirality. 2008. 20. P. 749–759. DOI: 10.1002/chir.20482.
Burmistrov V.A., Alexandrijskiy V.V., Koifman O.I. Orienta-tion properties of complexes with hydrogen bond non-meso-morphic component - liquid crystal. nematic solutions of n-ni-troaniline. Journal of Physical Chemistry (Rus.). 1991. V. 65. №3. P. 694–698.
Burmistrov V.A., Alexandrijskiy V.V., Koifman O.I. "Hydro-gen bonding in thermotropic liquid crystals" M.: KRASAND, 2013. 352 p. (in Russia).
Gottarelli G., Spada G.P. Induced Cholesteric Mesophases: Origin and Application, Mol. Cryst. Liq. Cryst. 1985. 123(1). P. 377388. DOI: 10.1080/00268948508074792.
Eelkema R., Feringa B.L. Amplification of chirality in liquid crystals. Org. Biomol. Chem. 2006. 4. Р. 3729–3745. DOI: 10.1039/b608749c.
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Scalman G., Barone V., Men-nucci B., Petersson G.A. Gaussian 09, Rev A.1; Gaussian Inc.: Wallingford, CT, USA, 2009.
Parr R.G., Yang W. Density-Functional Theory of Atoms and Molecules. – N. Y. Oxford University Press, 1989. 333 p.
Becke A.D. J. Chem. Phys. 1993. 98. P. 5648–5652. DOI:10.1063/1.464913.
Zhurko G.A., Aleksandriyskiy V.V., Burmistrov V.A. The use of quantum-chemical calculations to study the molecular structure of some nematic schif bases. Liq. Cryst. and their Appl. 2005. N 1-2. P. 13–23.
Andrienko G.A. Chemcraft, v. 1.8. http://www.chem-craftprog.com.
Dunmur D.A., Fukuda A., Luckhurst G.R. Physical proper-ties of liquid crystals: nematics. INSPEC, London, United Kingdom. 2001.
Blinov L.M. Structure and Properties of Liquid Crystals, Springer. 2011. XVIII. 439 p. http://www.springer.com/978-90-481-8828-4.