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.
1. [1]
  Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
2. [2]
  Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp³) and C(sp)-C(sp²) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
3. [3]
  Weimei Zeng , Youai Qiu . Electrochemical C-H carboxylation of benzylamines. Chinese Chemical Letters, 2026, 37(1): 111679-. doi: 10.1016/j.cclet.2025.111679
4. [4]
  Jiao Li , Chenyang Zhang , Chuhan Wu , Yan Liu , Xuejian Zhang , Xiao Li , Yongtao Li , Jing Sun , Zhongmin Su . Defined organic-octamolybdate crystalline superstructures derived Mo₂C@C as efficient hydrogen evolution electrocatalysts. Chinese Chemical Letters, 2024, 35(6): 108782-. doi: 10.1016/j.cclet.2023.108782
5. [5]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
6. [6]
  Junyou Ding , Xiaotong Li , Hongmin Lin , Bochao Ye , Xing Zhou , Feihu Cui , Yingming Pan , Haitao Tang . Highly regioselective hydrogermylation of unsaturated C-C bonds over ligand-control single atom palladium catalysts. Chinese Chemical Letters, 2025, 36(11): 111286-. doi: 10.1016/j.cclet.2025.111286
7. [7]
  Tian-Zhang Wang , Le-Yu Tang , Yu-Qiu Guan , Lingfei Hu , Gang Lu , Yu-Feng Liang . Nickel-catalyzed reductive alkynylation of ketoimines via unstrained C–C bond activation. Chinese Chemical Letters, 2025, 36(11): 111050-. doi: 10.1016/j.cclet.2025.111050
8. [8]
  Yuwei Liang , Jianwei Huang , Zhiqiang Zhang , Qinghong Yang , Aiwen Lei , Hong Yi . Electrochemical Mn-catalyzed nitrogenation of alkynes to nitriles via C≡C bonds cleavage. Chinese Chemical Letters, 2026, 37(4): 111166-. doi: 10.1016/j.cclet.2025.111166
9. [9]
  Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
10. [10]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
11. [11]
  Chen Li , Ziyuan Zhao , Shouyun Yu . Photoredox-catalyzed C-glycosylation of peptides with glycosyl bromides. Chinese Chemical Letters, 2024, 35(6): 109128-. doi: 10.1016/j.cclet.2023.109128
12. [12]
  Hongjin Shi , Guoyin Yin , Xi Lu , Yangyang Li . Stereoselective synthesis of 2-deoxy-α-C-glycosides from glycals. Chinese Chemical Letters, 2024, 35(12): 109674-. doi: 10.1016/j.cclet.2024.109674
13. [13]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
14. [14]
  Yunzhe Du , Siliu Cheng , Shuyi Li , Junping Niu , Yuan Gou , Ligang Yan , Tian-Xing Zhang , Ruijun Xie , Limin Han , Tiezheng Jia , Ning Zhu . C2-Transformation of calcium carbide trigered by hydrogen sulfide. Chinese Chemical Letters, 2025, 36(12): 111233-. doi: 10.1016/j.cclet.2025.111233
15. [15]
  Qianwei Chen , Yuan Xi , Zhuangzhi Shi . Germanium-directed C–H borylation by iridium catalysis. Chinese Chemical Letters, 2026, 37(8): 112107-. doi: 10.1016/j.cclet.2025.112107
16. [16]
  Qing Tang , Kai Zhao , Hui-Hui Zhu , Qiang Lin , Hai-Yue Zhao , Wei-Xuan Zheng , Zhong-Nan Wu , Hao Wang , Guo-Cai Wang , Yu-Bo Zhang . Pecanthines A–C, unprecedented dimeric β-carboline alkaloids from the seeds of Peganum harmala. Chinese Chemical Letters, 2026, 37(10): 112172-. doi: 10.1016/j.cclet.2025.112172
17. [17]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
18. [18]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
19. [19]
  Yi Liu , Zhe-Hao Wang , Guan-Hua Xue , Lin Chen , Li-Hua Yuan , Yi-Wen Li , Da-Gang Yu , Jian-Heng Ye . Photocatalytic dicarboxylation of strained C–C bonds with CO₂ via consecutive visible-light-induced electron transfer. Chinese Chemical Letters, 2024, 35(6): 109138-. doi: 10.1016/j.cclet.2023.109138
20. [20]
  Jiajun Wang , Guolin Yi , Shengling Guo , Jianing Wang , Shujuan Li , Ke Xu , Weiyi Wang , Shulai Lei . Computational design of bimetallic TM₂@g-C₉N₄ electrocatalysts for enhanced CO reduction toward C₂ products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1803)
HTML views(36)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142