SYNTHESIS AND MESOMORPHIC PROPERTIES OF NEW ROD-LIKE HETEROCYCLIC LIQUID CRYSTALS

Authors

  • Foo KOK-LEEI Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia. Corresponding author: hast@utar.edu.my.
  • Ha SIE-TIONG Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, 31900 Kampar, Perak, Malaysia. Corresponding author: hast@utar.edu.my.
  • Guan-Yeow YEAP Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Penang, Malaysia. Corresponding author: hast@utar.edu.my. https://orcid.org/0000-0002-5115-9594
  • Hong-Cheu LIN Department of Materials Science & Engineering, National Chiao Tung University, Taiwan, ROC. Corresponding author: hast@utar.edu.my. https://orcid.org/0000-0001-8699-9641

DOI:

https://doi.org/10.24193/subbchem.2020.4.11

Keywords:

benzothiazole, Schiff base, nematic, smectic A

Abstract

Structure-property relationship is one of the most important research areas in the liquid crystals. Therefore, in the present work, we studied a new series of rod-like heterocyclic liquid crystals, 6-methyl-2-[4-(4-alkoxybenzoyloxy)benzylideneamino]benzothiazoles. The rod-like molecules having heterocyclic and two phenyl rings as core system, imine and ester as linking units, long alkoxy chain at the terminal position. There are six members in the series with different length of alkoxy chain (CnH2n+1O-, where n = 6, 8, 10, 12, 14, 16). The structures of the compounds were elucidated using spectroscopic techniques. Their mesomorphic behaviours were determined by differential scanning calorimetry, polarizing optical microscopic and powder X-ray diffraction techniques. Members with shorter alkoxy chain (n = 6, 8, 10) exhibited single mesophase (nematic). As the alkoxy chain increased to n = 12, 14, 16, the nematic phase appeared together with an additional mesophase (smectic). The phase width was dependent on the alkoxy chain length. The incorporation of the methyl substituent at the sixth position (lateral) of the benzothiazole able to increase the clearing point and widen the mesophase width of the compounds.

References

K.C. Zhao; J.Q. Du; H.F. Wang; K.Q. Zhao; P. Hu; B.Q. Wang; H. Monobe; B. Heinrich; B. Donnio; Chem. Asian J., 2019, 14(3), 462-470.

W. Zhang; T. Sakurai; M. Aotani; G. Watanabe; H. Yoshida; V.S. Padalkar; Y. Tsutsui; D. Sakamaki; M. Ozaki; S. Seki; Adv. Opt. Mater.; 2019, article number 1801349.

B.B. Chakraborty; S. Anwar; S. Das; S.B. Paul; G. Mohiuddin; J. De; S. Choudhury; Liq. Cryst.; 2018, 45(11), 1644-1653.

F.N. da Silva; A.S. da Silva; I.H. Bechtold; E. Zapp; A.A. Vieira; Liq. Cryst., 2019, 46(11), 1707-1717.

A.J. Seed; P. Sampson; Liq. Cryst., 2017, 44(12-13), 1894-1910.

E. Girotto, I.H. Bechtold, H. Gallardo; Liq. Cryst., 2016, 43(12), 1768-1777.

D. Shi, K. Hu; P. Chen; W. Du; A. Gao; R. Chen; X. Chen; Z. An; Liq. Cryst., 2016, 43(10), 1397-1407.

L.L. Lai; C.H. Wang; W.P. Hsien; H.C. Lin; Mol. Cryst. Liq. Cryst., 1996, 287, 177-181.

B.B. Chakraborthy; S. Anwar; S. Das; S.B. Paul; G. Mohiuddin; J. De; S. Choudhury; Liq. Cryst.; 2018, 45, 1644-1653.

M.L. Parra; E.Y. Qlgueta; J.A. Ulloa; J.M. Vergara; Al. Sanchez; Liq. Cryst., 2012, 39(8), 917-925.

J. Seltmann; M. Lehmann; Liq. Cryst., 2011, 38(4), 407-422.

W.L. Chia; C.W. Lin; Liq. Cryst., 2013, 40, 922–931.

M.Z. Shafikov, A.M. Prokhorov; D.W. Bruce; Liq. Cryst., 2017, 44(4), 705-712.

M. Hagar; H. Ahmed; O. Alhaddad; Liq. Cryst., 2019, 46(9), 1440-1451.

P.J. Collings; M. Hird M; Introduction to Liquid Crystals: Chemistry and Physics, Taylor & Francis Ltd., UK, 1998.

G. Karanlik; H. Ocak; B. Bilgin Eran; J. Mol. Liq., 2019, 275, 567-577.

M. Hagar; H.A. Ahmed; G.R. Saad; Liq. Cryst., 2018, 45(9), 1324-1332.

H.A. Ahmed; M. Hagar; T.H. El-Sayed; R.B. Alnoman; Liq. Cryst., 2019, 46(7), 1156-1166.

M. Hagar; H.A. Ahmed; G.R. Saad; J. Mol. Liq., 2019, 273, 266-273.

V.S. Sharma; R.B. Patel; Mol. Cryst. Liq. Cryst., 2017, 648(1), 53-65.

C. Selvarasu; P. Kannan; Mol. Cryst. Liq Cryst., 2017, 648(1), 77-87.

C. Selvarasu; P. Kannan; J. Mol Liq., 2016, 1125, 234-240.

B.T. Thaker; D.B. Solanki; B.S. Patel; N.B. Patel; Liq. Cryst., 2013, 40(9), 1296-1309.

V.S. Sharma; R.B. Patel; Mol. Cryst. Liq. Cryst., 2017, 643(1), 141-158.

T.M. Koh; S.T. Ha; G.Y. Yeap; H.C. Lin; Chin. Chem. Lett., 2013, 24, 926-928.

K.L. Foo; S.T. Ha; G.Y. Yeap; H.C. Lin; Phase Trans., 2019, 92(1), 87-99.

S.T. Ha; T.M. Koh; H.C. Lin; G.Y. Yeap; Y.F. Win; S.T. Ong; Y. Sivasothy; L.K. Ong; Liq. Cryst., 2009, 36(9), 917-925.

G.Y. Yeap; T.C. Hng; D. Takeuchi; K. Osakada; W.A.K. Mahmood; M.M. Ito; Mol. Cryst. Liq. Cryst., 2009, 506, 134-149.

G.M. Paterno; V. Robbiano; K.J. Fraser; C. Frost; V. Garcia Sakai; F. Cacialli; Sci. Rep., 2017, 7, 41013.

D. Demus; L. Richter; Textures of Liquid Crystals, Verlag Chemie, New York, 1978.

I. Dierking, Textures of Liquid Crystals, Wiley-VCH, Weinheim, 2003.

B.Y. Zhang; Y.G. Jia; D.S. Yao; X.W. Dong; Liq. Cryst., 2004, 31, 339-345.

D. Pociecha; D. Kardas; E. Gorecka; J. Szydlowska; J. Mieczkowski; D. Guillon; J. Mater. Chem., 2003, 13, 34-37.

R.A. Reddy; B.K. Sadashiva; J. Mater. Chem., 2004, 14, 310-319.

K.C. Majumdar; S. Mondal; N. Pal; P.K. Sinha; Tetrahedron Lett., 2009, 50, 1992-1995.

Q. Wei; L. Shi; H. Cao; L.P. Wang; H. Yang; Y.B. Wang; Liq. Cryst., 2008, 35, 581-585.

G.W. Gray; Molecular Structure and the Properties of Liquid Crystals, Academic Press, London, 1962.

P. Berdague; J.P. Bayle; M.S. Ho; B.M. Fung; Liq. Cryst., 1993, 14, 667-674.

P.J. Collings; M. Hird; Introduction to Liquid Crystals: Chemistry and Physics, Taylor & Francis Ltd., UK, 1998.

G.Y. Yeap; S.T. Ha; P.L. Lim; P.L. Boey; M.M. Ito; S. Sanehisa; Y. Youhei; Liq. Cryst., 2006, 33(2), 205-211.

K.L. Foo; S.T. Ha; F.W. Yip; G.Y. Yeap; H.C. Lin; S.S. Sastry; Liq. Cryst., 2014, 41(11), 1516-1525.

S.T. Ha; T.M. Koh; F.W. Yip; S.S. Sastry; Liq. Cryst., 2013, 40(8), 1016-1023.

O.N. Kadkin; H. Han; Y.G. Galyametdinov; J. Organomet. Chem., 2007, 692, 5571-5582.

A.B. Lutjen, M.A. Quirk, A.M. Barbera, E.M. Kolonko; Bioorg. Med. Chem., 2018, 26, 5291-5298.

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Published

2020-12-30

How to Cite

KOK-LEEI, F. ., SIE-TIONG , H. ., YEAP, G.-Y. ., & LIN, H.-C. . (2020). SYNTHESIS AND MESOMORPHIC PROPERTIES OF NEW ROD-LIKE HETEROCYCLIC LIQUID CRYSTALS. Studia Universitatis Babeș-Bolyai Chemia, 65(4), 135–150. https://doi.org/10.24193/subbchem.2020.4.11

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