Citation: Teck-Ming Koh, Sie-Tiong Ha, Guan-Yeow Yeap, Hong-Cheu Lin. New mesomorphic benzothiazol derivatives：Synthesis and characterization[J]. Chinese Chemical Letters, ;2013, 24(10): 926-928. shu

New mesomorphic benzothiazol derivatives：Synthesis and characterization

1.
a Faculty of Engineering & Science, Universiti Tunku Abdul Rahman, Jln Genting Klang, Setapak, Kuala Lumpur 53300, Malaysia;
2.
b Faculty of Science, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, Kampar 31900, Malaysia;
3.
c Centre for Biodiversity Research, Universiti Tunku Abdul Rahman, Jln Universiti, Bandar Barat, Kampar 31900, Malaysia;
4.
d Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Malaysia;
5.
e Department of Materials Science & Engineering, National Chiao Tung University, Hsinchu 300, Taiwan, China

Corresponding author: Sie-Tiong Ha,
Received Date: 12 April 2013
Available Online: 29 May 2013

In this paper, the synthesis of new mesomorphic benzothiazolyl derivatives, 6-ethoxy-2-[4-(4-alkyloxybenzoyloxy)benzylidenamino]benzothiazoles, is presented. The structures of the title compounds were elucidated using spectroscopic techniques, such as FT-IR, NMR (¹H and ¹³C), elemental analysis and EI-MS. The mesomorphic behaviours of these compounds were determined by differential scanning calorimetric and polarizing optical microscopic techniques. Compounds exhibited nematic and tilted smectic phases upon heating from crystal phase. An obvious odd-even effect was observed in this homologous series.
- Benzothiazole,
- Nematic,
- Smectic C,
- Mesomorphic
1. [1]
  [1] D. Adam, F. Closs, T. Frey, et al., Transient photoconductivity in a discotic liquid crystal, Phys. Rev. Lett. 70 (1993) 457-460.
2. [2]
  [2] M.R. Huang, X.G. Li, J. Wang, Liquid crystalline polyaniline and its derivatives, Tongji Daxue Xuebao 31 (2003) 848-852 (in Chinese).
3. [3]
  [3] X.G. Li, M.R. Huang, W. Duan, Y.L. Yang, Novel multifunctional polymers from aromatic diamines by oxidative polymerizations, Chem. Rev. 102 (2002) 2925-3030.
4. [4]
  [4] X.G. Li, Q.F. Lu, M.R. Huang, Self-stabilized nanoparticles of intrinsically conducting co-polymers from 5-sulfonic-2-anisidine, Small 4 (2008) 1201-1209.
5. [5]
  [5] X.G. Li, M.R. Huang, Facile optimal synthesis of inherently electroconductive polythiophene nanoparticles, Chem. Eur. J. 15 (2009) 6446-6455.
6. [6]
  [6] W. Pisula, M. Zorn, J.Y. Chang, K. Mullen, R. Zentel, Liquid crystalline ordering and charge transport in semiconducting materials, Macromol. Rapid Commun. 30 (2009) 1179-1202.
7. [7]
  [7] B.P. Chandra, N. Periasamy, J.N. Das, Triboluminescence, a new tool to investigate fracture-initiation time of crystals under stress, Pramana 8 (1977) 395-401.
8. [8]
  [8] M. Funahashi, J. Hanna, Fast hole transport in a new calamitic liquid crystal of 2-(40-heptyloxyphenyl)-6-dodecylthiobenzothiazole, Phys. Rev. Lett. 78 (1997) 2184-2187.
9. [9]
  [9] A. Ohno, A. Haruyama, K. Kurotaki, J. Hanna, Charge-carrier transport in smectic mesophases of biphenyls, J. Appl. Phys. 102 (2007) 083711.
10. [10]
  [10] S.T. Ha, T.M. Koh, G.Y. Yeap, et al., Synthesis and mesomorphic properties of 2-(4-alkyloxyphenyl)benzothiazoles, Mol. Cryst. Liq. Cryst. 506 (2009) 56-70.
11. [11]
  [11] S.T. Ha, T.M. Koh, H.C. Lin, et al., Heterocyclic benzothiazole-based liquid crystals: synthesis and mesomorphic, Liq. Cryst. 36 (2009) 917-925.
12. [12]
  [12] S.T. Ha, T.M. Koh, S.T. Ong, Y. Sivasothy, Synthesis and mesomorphic behavior of benzothiazole-based liquid crystals having terminal methoxyl group, Chin. Chem. Lett. 20 (2009) 1449-1452.
13. [13]
  [13] S.T. Ha, T.M. Koh, G.Y. Yeap, et al., Mesogenic Schiff base esters with benzothiazole core: synthesis and phase transition studies, Phase Transitions 83 (2010) 195-204.
14. [14]
  [14] L.L. Lai, C.H. Wang, W.P. Hsien, H.C. Lin, Synthesis and characterization of liquid crystalline molecules containing the quinoline unit, Mol. Cryst. Liq. Cryst. 287 (1996) 177-181.
15. [15]
  [15] O.N. Kadkin, H. Han, Y.G. Galyametdinov, Synthesis, computational modelling and liquid crystalline properties of some [3]ferrocenophane-containing Schiff's bases and β-aminovinylketone: molecular geometry-phase behaviour relationship, J. Organomet. Chem. 692 (2007) 5571-5582.
16. [16]
  [16] G.Y. Yeap, S.T. Ha, P.L. Boey, et al., Synthesis and mesomorphic properties of Schiff base esters ortho-hydroxy-para-alkyloxybenzylidene-para-substituted anilines, Mol. Cryst. Liq. Cryst. 452 (2006) 73-84.
17. [17]
  [17] Analytical and spectroscopic data for the representative compound C₂H₅O-9BSPEP: EI-MS m/z (rel. int. %): 544 (22) [M⁺], 247 (100), IR v_max (KBr, cm^-1): v 3056 (C-H aromatic); 2922, 2851 (C-H aliphatic); 1740 (C5O ester); 1609 (C5N thiazole), 1273 (C-O, aromatic ether) ¹H NMR (400 MHz, CDCl₃): d 0.9 (t, 3H, J = 6.6 Hz, CH₃-), 1.3 (m, 10H, CH₃-(CH₂)₅-(CH₂)₃-O-), 1.4 (t, 3H, J = 6.8 Hz, CH₃-CH₂-O-), 1.5 (p, 2H, J = 6.1 Hz,-CH₂-CH₂-CH₂-O-), 1.8 (p, 2H, J = 7.1 Hz,-CH₂-CH₂-O-), 4.0 (t, 2H, J = 6.6 Hz,-CH₂-O-), 4.1 (t, 2H, J = 7.1 Hz, CH₃-CH₂-O-), 7.0 (d, 2H, J = 8.8 Hz, Ar-H), 7.1 (d, 1H, J = 9.0 Hz, Ar-H), 7.3 (s, 1H, Ar-H), 7.4 (d, 2H, J = 8.6 Hz, Ar-H), 7.9 (d, 1H, J = 8.8 Hz, Ar-H), 8.1 (d, 2H, J = 8.6 Hz, Ar-H), 8.2 (d, 2H, J = 8.8 Hz, Ar-H), 9.0 (s, 1H,-N₅CH-); ¹³C NMR (100 MHz, CDCl₃): δ 14.23 (CH₃-), 14.94 (CH₃-CH₂O-), 15.01, 22.77, 26.07, 29.17, 29.35, 29.46, 29.61, 31.97 for methylene carbons (CH₃-(CH₂)₈-), 64.18 (-CH₂O-), 68.47 (CH₃-CH₂O-), 105.14, 114.50, 116.22, 121.06, 122.70, 123.85, 131.44, 132.50, 133.98, 135.93, 146.06, 154.91, 156.04, 157.18 for aromatic carbons, 163.88 (N=CH, Schiff base), 164.47 (N=C, thiazole), 169.20 (-COO-). Anal. calcd. for C₃₂H₃₆N₂O₄S: C, 70.56, H, 6.66, N, 5.14; Found: C, 70.48, H, 6.74, N, 5.03.
18. [18]
  [18] D. Demus, L. Richter, Textures of Liquid Crystals, Verlag Chemie, New York, 1978.
19. [19]
  [19] I. Dierking, Textures of Liquid Crystals, Wiley-VCH, Weinheim, 2003.
20. [20]
  [20] Q. Wei, L. Shi, H. Cao, L.P. Wang, H. Yang, Synthesis and mesomorphic properties of two series of new azine-type liquid crystals, Liq. Cryst. 35 (2008) 581-585.
21. [21]
  [21] M.A. Guillevic, M.E. Light, S.J. Coles, et al., Synthesis of dinuclear complexes of rhenium(I) as potential metallomesogens, J. Chem. Soc. Dalton Trans. 9 (2000) 1437-1445.
22. [22]
  [22] P.A. Henderson, R.T. Inkster, J.M. Seddon, C.T. Imrie, Highly non-linear liquid crystal tetramers, J. Mater. Chem. 11 (2001) 2722-2731.
23. [23]
  [23] G.Y. Yeap, T.C. Hng, D. Takeuchi, et al., Non-symmetric liquid crystal dimers: high thermal stability in nematic phases enhanced by thiophene-2-carboxylate moieties, Mol. Cryst. Liq. Cryst. 506 (2009) 134-149.
24. [24]
  [24] A.K. Prajapati, N.L. Bonde, Mesogenic benzothiazole derivatives with methoxy substituents, J. Chem. Sci. 118 (2006) 203-210.
25. [25]
  [25] A.K. Prajapati, N.L. Bonde, Mesogenic benzothiazole derivatives with a polar nitro substituent, Mol. Cryst. Liq. Cryst. 501 (2009) 72-85.
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1.
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