Synthesis and Characterization of Thermotropic Liquid Crystals Consisting Heterocyclic Benzothiazole Core System

Kok-Leei Foo; Sie-Tiong Ha; Siew-Ling Lee

doi:10.14233/ajchem.2014.17135

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Issue Published : November 6, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Characterization of Thermotropic Liquid Crystals Consisting Heterocyclic Benzothiazole Core System

https://doi.org/10.14233/ajchem.2014.17135

Kok-Leei Foo

Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia

Sie-Tiong Ha

Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia

Siew-Ling Lee

Ibnu Sina Institute for Fundamental Science Studies, Universiti Teknologi Malaysia, 81310 UTM Skudai, Johor, Malaysia

Corresponding Author(s) : Sie-Tiong Ha

hast_utar@yahoo.com

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22
Article Published : November 6, 2014

Abstract

A new series of rod-shaped mesomorphic compounds, 6-methyl-2-(4-alkoxybenzylidenamino)benzothiazoles bearing a fused thiazole ring and imine central linkage, were prepared and their molecular structures were confirmed via mass spectrometric, IR and NMR spectroscopic techniques. The mesomorphic properties were identifed using differential scanning calorimetry, polarizing optical microscopy and X-ray diffraction analysis. All compounds showed enantiotropic mesomorphism. Whilst the lower members of the series, butyloxy, hexyloxy and octyloxy derivatives exhibited nematic phase, the medium members (decyloxy derivative) exhibited nematic and smectic A phases. The higher members (C12, C14, C16 and C18 derivatives) displayed smectic A phase only.

Keywords

Imine Benzothiazole Mesomorphic Nematic Smectic

Foo, K.-L., Ha, S.-T., & Lee, S.-L. (2014). Synthesis and Characterization of Thermotropic Liquid Crystals Consisting Heterocyclic Benzothiazole Core System. Asian Journal of Chemistry, 26(22), 7627–7631. https://doi.org/10.14233/ajchem.2014.17135

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References

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S.-T. Ha, T.-M. Koh, H.-C. Lin, G.-Y. Yeap, Y.-F. Win, S.-T. Ong, Y. Sivasothy and L.-K. Ong, Liq. Cryst., 36, 917 (2009); doi:10.1080/02678290903131278.
A.K. Prajapati and V. Modi, Liq. Cryst., 37, 1281 (2010); doi:10.1080/02678292.2010.504861.
K.C. Majumdar, S. Mondal, N. Pal and R.K. Sinha, Tetrahedron Lett., 50, 1992 (2009); doi:10.1016/j.tetlet.2009.02.065.
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M.R. Fisch and S. Kumar, Introduction of Liquid Crystals, In: Liquid Crystal: Experimental Study and Physical Properties and Phase Transition, Cambridge University Press, United Kingdom, pp. 1-26 (2001).
G.Y. Yeap, S.T. Ha, P.L. Lim, P.L. Boey, M.M. Ito, S. Sanehisa and Y. Youhei, Mol. Cryst. Liq. Cryst., 33, 205 (2006).
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References

J.W. Goodby, V. Görtz, S.J. Cowling, G. Mackenzie, P. Martin, D. Plusquellec, T. Benvegnu, P. Boullanger, D. Lafont, Y. Queneau, S. Chambert and J. Fitremann, Chem. Soc. Rev., 36, 1971 (2007); doi:10.1039/b708458g.

C.K. Lai, H.C. Liu, F.J. Li, K.L. Cheng and H.S. Sheu, Liq. Cryst., 32, 85 (2005); doi:10.1080/02678290512331324048.

A. Seed, Chem. Soc. Rev., 36, 2046 (2007); doi:10.1039/b612666a.

S.T. Ha, T.M. Koh, S.T. Ong and Y. Sivasothy, Chin. Chem. Lett., 20, 1449 (2009); doi:10.1016/j.cclet.2009.06.023.

A.K. Prajapati and N.L. Bonde, Mol. Cryst. Liq. Cryst., 501, 72 (2009); doi:10.1080/15421400802697616.

A.I. Pavluchenko, N.I. Smirnova, V.V. Titov, E.I. Kovshev and K.M. Djumaev, Mol. Cryst. Liq. Cryst., 37, 35 (1976); doi:10.1080/15421407608084344.

S.T. Ha, K.L. Foo, H.C. Lin, M.M. Ito, K. Abe, K. Kunbo and S.S. Sastry, Chin. Chem. Lett., 23, 761 (2012); doi:10.1016/j.cclet.2012.04.025.

S.T. Ha, T.M. Koh, S.L. Lee, G.Y. Yeap, H.C. Lin and S.T. Ong, Liq. Cryst, 37, 547 (2010); doi:10.1080/02678291003710425.

S.T. Ha, T.M. Koh, G.Y. Yeap, H.C. Lin, S.L. Lee, Y.F. Win and S.T. Ong, Phase Transit., 83, 195 (2010); doi:10.1080/01411591003600375.

D. Demus and L. Ritcher, Textures of Liquid Crystals, Verlag Chemie, New York (1978).

L. Dierking, Textures of Liquid Crystals, Wiley-VCH, Weinheim (2003).

G.-Y. Yeap, T.-C. Hng, D. Takeuchi, K. Osakada, W.A.K. Mahmood and M.M. Ito, Mol. Cryst. Liq. Cryst., 506, 134 (2009); doi:10.1080/15421400902987248.

S.-T. Ha, T.-M. Koh, H.-C. Lin, G.-Y. Yeap, Y.-F. Win, S.-T. Ong, Y. Sivasothy and L.-K. Ong, Liq. Cryst., 36, 917 (2009); doi:10.1080/02678290903131278.

A.K. Prajapati and V. Modi, Liq. Cryst., 37, 1281 (2010); doi:10.1080/02678292.2010.504861.

K.C. Majumdar, S. Mondal, N. Pal and R.K. Sinha, Tetrahedron Lett., 50, 1992 (2009); doi:10.1016/j.tetlet.2009.02.065.

P.J. Collings and M. Hird, Calamitic Liquid Crystals-Nematic and Smectic Mesophases. In: Introduction to Liquid Crystal Chemistry and Physics, Taylor and Francis Ltd., London, pp. 43-77 (1997).

M.R. Fisch and S. Kumar, Introduction of Liquid Crystals, In: Liquid Crystal: Experimental Study and Physical Properties and Phase Transition, Cambridge University Press, United Kingdom, pp. 1-26 (2001).

G.Y. Yeap, S.T. Ha, P.L. Lim, P.L. Boey, M.M. Ito, S. Sanehisa and Y. Youhei, Mol. Cryst. Liq. Cryst., 33, 205 (2006).

C.C. Liao, C.S. Wang, H.S. Sheu and C.K. Lai, Tetrahedron, 64, 7977 (2008); doi:10.1016/j.tet.2008.06.001.

H.S. Wang, Y.-J. Wang, H.-M. Hu, G.-H. Lee and C.K. Lai, Tetrahedron, 64, 4939 (2008); doi:10.1016/j.tet.2008.03.101.

R.A. Reddy and B.K. Sadashiva, J. Mater. Chem., 14, 310 (2004); doi:10.1039/b309262c.

Issue

Vol. 26 No. 22 (2014): Vol 26 Issue 22

Synthesis and Characterization of Thermotropic Liquid Crystals Consisting Heterocyclic Benzothiazole Core System

Corresponding Author(s) : Sie-Tiong Ha

Abstract

Keywords

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