Six-Armed Structures Based on Benzene Ring, Synthesis and Characterization via Sonogashira Coupling

Mohammed Hadi Ali Al-Jumaili; Ahmed Solaiman Hamed; Nihat Akkurt; Lokman Torun

doi:10.22146/ijc.49419

Six-Armed Structures Based on Benzene Ring, Synthesis and Characterization via Sonogashira Coupling

https://doi.org/10.22146/ijc.49419

Mohammed Hadi Ali Al-Jumaili^(1*), Ahmed Solaiman Hamed⁽²⁾, Nihat Akkurt⁽³⁾, Lokman Torun⁽⁴⁾

(1) Department of Chemistry, Faculty of Science and Arts, Yildiz Technical University, İstanbul, Turkey; College of Dentistry, Al Turath University College, Baghdad, Iraq
(2) Department of Chemistry, College of Applied Science, University of Fallujah, Al-Anbar, Iraq
(3) Department of Chemistry, Faculty of Science and Art, Kirklareli University, Kirklareli, Turkey
(4) TORKIM ARGE Inc. Yildiz Technical University, Technology Developing Zone, Incubation Center, 34220 Esenler, İstanbul, Turkey
(*) Corresponding Author

Abstract

A new six-armed compounds consist of benzene ring as a central core substituted with aromatic ring and three rod-like armed of 2-chloro-4,6-bis(dodecyloxy)-1,3,5-triazine as the peripheral arms unit which obtained by sequential nucleophilic substitution of chlorine atoms in cyanuric chloride. The substitution took place at the acetylenic periphery on the central benzene ring by Sonogashira coupling. Equimolar mixtures of the six-armed compounds based on the benzene core with the complementary 4-dodecyloxybenzoic acid, which already possessed liquid crystal property, resulted in an organic salt. The organic salts and structures were investigated by differential scanning calorimetry (DSC), and confirmed by spectroscopic methods (¹H-NMR, ¹³C-NMR and Mass spectroscopy)

Keywords

Triazine, liquid crystals, hydrogen bonding, benzene core derivatives, synthesis and characterization.

Full Text:

Full Text PDF

References

[1] He, X.H., Han, L., Meng, F.B., Tian, M., and Zhang, B.Y., 2012, The effect of different arms on the properties of chiral branched-arm liquid crystals based on isosorbide as the chiral core, Liq. Cryst., 39 (6), 779–787.

[2] Wang, X., Bai, L., Kong, S., Song, Y., and Meng, F., 2019, Star-shaped supramolecular ionic liquid crystals based on pyridinium salts, Liq. Cryst., 46 (4), 512–522.

[3] Novotná, V., Bobrovsky, A., Shibaev, V., Pociecha, D., Kašpar, M., and Hamplová, V., 2016, Synthesis, phase behavior and photo-optical properties of bent-core methacrylate with azobenzene group and corresponding side-chain polymethacrylate, RSC Adv., 6 (70), 65747–65755.

[4] He, W.L., Huang, Q., Yang, Z., Cao, H., Wang, D., and Yang, H., 2015, Effect of bent-shape and calamitic-shape of hydrogen-bonded mesogens on the liquid crystalline properties, Liq. Cryst., 42 (8), 1191–1200.

[5] Doganci, E., and Davarci, D., 2019, Synthesized and mesomorphic properties of cholesterol end-capped poly (ε-caprolactone) polymers, J. Polym. Res., 26 (7), 165.

[6] Zhang, B.Y., Yao, D.S., Meng, F.B., and Li, Y.H., 2005, Structure and properties of novel three-armed star-shaped liquid crystals, J. Mol. Struct., 741 (1-3), 135–140.

[7] Judele, R., Laschat, S., Baro, A., and Nimtz, M., 2006, Gallic esters of 4,5-dinitrocatechol as potential building blocks for thermotropic liquid crystals, Tetrahedron, 62 (41), 9681–9687.

[8] Salisu, A.A., 2016, Synthesis and characterization of three-arm star-shaped glassy liquid crystal containing biphenyl esters, ChemSearch J., 7 (1), 37–42.

[9] Caminade, A.M., and Majoral, J.P., 2018, Engineering CNDP’s of dendrimers containing phosphorous interior compositions to produce new emerging properties, J. Nanopart. Res., 20 (3), 74.

[10] Imrie, C.T., Henderson, P.A., and Yeap, G.Y., 2009, Liquid crystal oligomers: going beyond dimers, Liq. Cryst., 36 (6-7), 755–777.

[11] Iftime, M.M., Cozan, V., Airinei, A., Varganici, C., Ailiesei, G., Timpu, D., and Sava, I., 2019, Asymmetric azomethine amines with azobenzene moieties–liquid crystalline and optical properties, Liq. Cryst., 46 (10), 1584–1594.

[12] Osman, F., Yeap, G.Y., Maeta, N., Ito, M.M., Lin, C.M., and Lin, H.C., 2017, Liquid crystalline non-linear S-shaped oligomers consisting of azobenzene and biphenylene units: Synthesis, characterisation and influence of central spacer, Liq. Cryst., 44 (14-15), 2355–2365.

[13] Wang, Y.J., Sheu, H.S., and Lai, C.K., 2007, New star-shaped triarylamines: Synthesis, mesomorphic behavior, and photophysical properties, Tetrahedron, 63 (7), 1695–1705.

[14] Bao, R., Pan, M., Qiu, J.J., and Liu, C.M., 2010, Synthesis and characterization of six-arm star-shaped liquid crystalline cyclotriphosphazenes, Chin. Chem. Lett., 21 (6), 682–685.

[15] Ge, L.N., Xian, S.W., Huang, Y., Min, Y., Lv, J.M., Tian, M., and Yao, D.S., 2018, Synthesis and mesomorphism of novel multi-arm liquid crystals with cholic acid as chiral centre linking Schiff base moieties as mesogens, Liq. Cryst., 45 (7), 1055–1067.

[16] Barberá, J., Bardají, M., Jiménez, J., Laguna, A., Martínez, M.P., Oriol, L., Serrano, J.L., and, and Zaragozano, I., 2005, Columnar mesomorphic organizations in cyclotriphosphazenes, J. Am. Chem. Soc., 127 (25), 8994–9002.

[17] Kanibolotsky, A.L., Perepichka, I.F., and Skabara, P.J., 2010, Star-shaped π-conjugated oligomers and their applications in organic electronics and photonics, Chem. Soc. Rev., 39 (7), 2695–2728.

[18] Tuzimoto, P., Santos, D.M.P.O., Moreira, T.S., Cristiano, R., Bechtold, I.H., and Gallardo, H., 2014, Luminescent liquid crystals containing a sulphur-based heterocyclic core, Liq. Cryst., 41 (8), 1097–1108.

[19] Gallardo, H., and Westphal, E., 2015, Importance of organic synthesis in the development of liquid crystals, Curr. Org. Synth., 12 (6), 806–821.

[20] Sarhan, A.A.O., and Izumi, T., 2003, Design and synthesis of new functional compounds related to ferrocene bearing heterocyclic moieties: A new approach towards electron donor organic materials, J. Organomet. Chem., 675 (1-2), 1–12.

[21] Salisu, A.A., and Kogo, A.A., 2010, New Liquid crystals in the series of 1,3,5-triazine compounds containing azobenzene at the peripheral arms, Bayero J. Pure Appl. Sci., 3 (1), 54–58.

[22] Didehban, K., Namazi, H., and Entezami, A.A., 2009, Triazine-based dendrimers as liquid crystals: synthesis and characterization, Iran. Polym. J., 18 (9), 731–741.

[23] Tan, L.S., Dalton, M., and Kannan, R., 2012, Two-photon absorbing cross-linked polyurethanes containing delphenylamino-dialkyffluorene-1,3,5-triazine units, U.S. Patent 8,318,888.

[24] Bhagavath, P., Shetty, R., and Sunil, D., 2019, 1,3,5-Triazine-based liquid crystals: An up-to-date appraisal of their synthetic design and mesogenic properties, Crit. Rev. Solid State Mater. Sci., 1-32.

[25] Meier, H., Holst, H.C., and Oehlhof, A., 2003, Star‐shaped compounds having 1,3,5‐triazine cores, Eur. J. Org. Chem., 2003 (21), 4173–4180.

[26] Lee, C.H., and Yamamoto, T., 2002, Synthesis of liquid-crystalline, highly luminescent π-conjugated 1,3,5-triazine derivatives by palladium-catalyzed cross-coupling reaction, Mol. Cryst. Liq. Cryst., 378 (1), 13–21.

[27] Beltrán, E., Serrano, J.L., Sierra, T., and Giménez, R., 2012, Functional star-shaped tris(triazolyl)triazines: Columnar liquid crystal, fluorescent, solvatofluorochromic and electrochemical properties, J. Mater. Chem., 22 (16), 7797–7805.

[28] Sundaram, S., Subhasri, P., Rajasekaran, T.R., Jayaprakasam, R., Senthil, T.S., and Vijayakumar, V.N., 2017, Observation of induced new smectic phase in supramolecular hydrogen bonded liquid crystals between mesogenic and non-mesogenic aliphatic compounds, Ferroelectrics, 510 (1), 103–120.

[29] Ambrožič, G., and Zigon, M., 2005, Hydrogen bonded liquid-crystalline polyurethane complexes with 4-dodecyloxybenzoic acid, Acta Chim. Slov., 52, 207–214.

[30] Nishihara, Y., Ikegashira, K., Hirabayashi, K., Ando, J., Mori, A., and, Hiyama, T., 2000, Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes, J. Org. Chem., 65 (6), 1780–1787.

[31] Kumar, C.R.S., Jha, A., and and Sastry, S.S., 2010, Induced crystal G phase of liquid crystalline amide through inter molecular hydrogen bonding, J. Non-Cryst. Solids, 356 (6-8), 334–339.

[32] Sıdır, Y.G., Sıdır, İ., and Demiray, F., 2017, Dipole moment and solvatochromism of benzoic acid liquid crystals: Tuning the dipole moment and molecular orbital energies by substituted Au under external electric field, J. Mol. Struct., 1137, 440–452.

[33] Stackhouse, P.J., Wilson, A., Lacey, D., and Hird, M., 2010, Synthesis and properties of novel columnar liquid crystals based on symmetrical and non-symmetrical 1,3,5-trisubstituted benzene derivatives, Liq. Cryst., 37 (9), 1191–1203.

[34] Akkurt, N., Al-Jumaili, M.H.A., Eran, B.B., Ocak, H., and Torun, L., 2019, Acetylene-bridged triazine π-conjugated structures: synthesis and liquid crystalline properties, Turk. J. Chem., 43, 1436–1444.

[35] Yang, R., Ding, L., Chen, W., Zhang, X., and Li, J., 2019, Molecular-weight dependence of phase structure and viscosity in a liquid crystalline polyester with strong π–π interaction, Liq. Cryst., 46 (3), 422-429.

DOI: https://doi.org/10.22146/ijc.49419