Abstract
The formation of a thermotropic smectic phase in 3,5-diamino-1-dodecyl-1,2,4-triazole was revealed by polarizing microscopy and DSC. Depending on heating and cooling conditions, transitions between different types of layered packings occur, which was evidenced by dielectric measurements. Quantum-chemical simulation established that the mesomorphism of 1,2,4-triazole derivatives is associated with the formation of supramolecules with a higher polarizability anisotropy. The calculation results confirmed the possibility of lateral hydrogen bonding which favors layered smectic packing.
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References
Lehn, J.-M., Supramolecular Chemistry. Concepts and Perspectives, Weinheim: VCH, 1995.
Kapustin, A.P. and Bykova, N.T., Kristallografiya, 1968, vol. 13, p. 345.
Paleos, C.M. and Tsiourvas, D., Liq. Cryst., 2001, vol. 28, no. 8, p. 1127. https://doi.org/10.1080/02678290110039516
Kajitani, T., J. Mater. Chem., 2004, vol. 14, p. 3449. https://doi.org/10.1039/B408672D
Kato, T., Kubota, Y., Nakano, M., and Uryu, T., Chem. Lett., 1995, vol. 24, no. 12, p. 1127. https://doi.org/10.1246/cl.1995.1127
Burmistrov, V.A., Aleksandriyskii, V.V., and Koifman, O.I.,, Vodorodnaya svyaz’ v termotropnykh zhidkikh kristallakh (Hydrogen Bond in Thermotropic Liquid Crystals), Moscow: KRASAND, 2013.
Kohmoto, S., Yamamoto, M., Kishikawa, K., and Kajitani, T., Mol. Cryst. Liq. Cryst., 2005, vol. 439, no. 1, p. 2039. https://doi.org/10.1080/15421400590954380
Danilova, E.A., Ivolin, A.A., Vorontsova, A.A., Islyaykin, M.K., Anan’yeva, G.A., Zharnikova, N.V., Bykova, VV, and Usol’tseva, N.V., Zhidk. Krist. Prakt. Ispol’z., 2011, no. 3, p. 17.
Moskvin, D.O., Sotsky, V.V., Danilova, E.A., Kudayarova, T. V., Smirnova, A.I., and Usol’tseva, N.V., Acta Phys. Polon. A, 2015, vol. 127, no. 4, p. 950. https://doi.org/10.12693/APhysPolA.127.950
Islyaykin, M.K., Danilova, E.A., and Kudrik, E.V.,, Uspekhi khimii porfirinov (Advances in Porphyrin Chemistry), Golubchikov, O.A., Ed., St. Peterburg: Nauch. Issled. Khimii Sankt-Peterb. Gos. Univ., 1999, vol. 2, p. 300.
Granik, G.V. and Grigor’ev, N.B., Oksid azota (NO): Novyi put’ k poisku lekarstv [Nitorgen Oxide (NO): New Way to Drug Design], Moscow: Vuzovskaya Kniga, 2004.
Granovskii, A.A., PC GAMESS, Version 7.0. http://classic.chem.msu.su/gran/gamess/index.html.
Parr, R.G. and Yang, W., Density Functional Theory of Atoms and Molecules, New York: Oxford Univ. Press, 1989.
Becke, A.D., J. Chem. Phys, 1993, vol. 98, p. 5648. https://doi.org/10.1063/1.464913
Andrienko, G.A., Chemcraft, vol. 1.8. http://www.chemcraftprog.com.
Aleksandriyskii, V.V, Novikov, I.V, and Burmistrov, V.A., Zh. Fiz. Khim., 1997, vol. 71, no. 6, p. 1133.
Funding
The work was funded by the Ministry for Education and Science of the Russian Federation in the framework of the State order (project no. 4. 1929.2017/4.6; for quantum-chemical calculations, project no. 4.3232.2017/4.6).
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Russian Text © The Authors(s), 2017, published in Rossiiskii Khimicheskii Zhurnal, 2017, Vol. 61, No. 2, pp. 68–74.
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Novikov, I.V., Aleksandriiskii, V.V., Kudayarova, T.V. et al. Mesomorphic and Dielectric Properties of Supramolecular 3,5-Diamino-1-dodecyl-1,2,4-triazole. Russ J Gen Chem 89, 1946–1951 (2019). https://doi.org/10.1134/S1070363219090342
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DOI: https://doi.org/10.1134/S1070363219090342