Citation: Yin Junxia, Wen Yanhao, Mao Zhipeng, Zhang Zhiyong, Guan Jintao, Yan Daoren. Synthesis and Properties of Thiadiazole Bent-Core Liquid Crystal with Difluorooxymethylene-Bridge[J]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 471-477. doi: 10.6023/cjoc201704016 shu

Synthesis and Properties of Thiadiazole Bent-Core Liquid Crystal with Difluorooxymethylene-Bridge

Department of Chemistry and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023

Corresponding author: Zhang Zhiyong, zzy6211@126.com
Received Date: 11 April 2017
Revised Date: 6 July 2017
Available Online: 11 February 2017
Fund Project: Project supported by the National Nutural Science Foundation of China (Nos. 11074054, 11374067)the National Nutural Science Foundation of China 11074054the National Nutural Science Foundation of China 11374067

Figures(6)

Bent-core liquid crystal has attracted much attention because of its unique photoelectric performance. However, the bent-Core liquid crystal has been developed slowly because of its narrow temperature range and high phase transformation temperature. In this paper, a series of novel bent-core liquid crystal compounds were designed and synthesized, which were based on 2, 5-disubstitueted-1, 3, 4-thiadiazole as the central units, difluorooxymethylene (CF₂O) as the linking group and straight alkyl as the terminal chain. The chemical structures of the target compounds were confirmed by IR, ¹H NMR, ¹³C NMR, and ¹⁹F NMR. Then, their transition temperatures and phase textures were investigated by using differential scanning calorimetric (DSC) and polarizing optical microscopy (POM). The result suggested that all the target compounds exhibited nematic phase and existed wide temperature range of nematic phase, and the widest range of nematic phase was 92.74℃. Compared with the structure oxadiazole bend-core liquid crystal, the melting point is slightly higher and liquid crystal phase temperature range is wider, which could provide material and theoretical basis for the further design and synthesis of novel wide-temperature nematic phase bent-core liquid crystal.
- thiadiazole,
- difluorooxymethylene,
- bent-core liquid crystal,
- nematic phase,
- synthesis
1. [1]
  Ros, M. B.; Serrano, J. L.; de La Fuente, M. R. J. Mater. Chem. 2005, 15, 5093. doi: 10.1039/b504384k
2. [2]
  Van Le K.; Dhara, S.; Sadashiva, B. K. Appl. Phys. 2006, 45, 1013.
3. [3]
  Zafiropoulos, N. A.; Lin, W. B.; Samulski, E. T. Liq. Cryst. 2009, 36, 649. doi: 10.1080/02678290902757768
4. [4]
  Madsen, L. A; Dingemans, T. J.; Nakata, M., Samulski, E. T. Phys. Rev. Lett.. 2004, 92, 145505(4).
5. [5]
  Lesac, A.; Nguyen, H. L.; Narančić, S.; Baumeister, U. Liq. Cryst. 2006, 33, 167. doi: 10.1080/02678290500168111
6. [6]
  Copper, L. L.; Samulski, E. T.; Scharrer, E. Cryst. Liq. Cryst. 2009, 511, 203.
7. [7]
  Tschierske, C.; Prehm, M. J. Mater. Chem. 2010, 20, 9658. doi: 10.1039/c0jm01919d
8. [8]
  Gleeson, H. F.; Kaur, S.; G rtz, V. Chem. Phys. 2014, 15, 1251.
9. [9]
  Jens, S.; Matthias, L. Liq. Cryst. 2011, 38, 407. doi: 10.1080/02678292.2010.550070
10. [10]
  Jens, S.; Alberto, M.; Benedetta, M.; Sonal, D. Chem. Mater. 2011, 23, 2630. doi: 10.1021/cm200643u
11. [11]
  Li, S. -Q.; Shen, D. Liq. Cryst. Disp. 2011, 26, 421(in Chinese).
12. [12]
  Du, Q. Master's Thesis, Wuhan Polytechnic University, Wuhan, 2012 (in Chinese).
13. [13]
  Wang, Y.; Du, Q.; Wang, G.; Zhang, Z.; Dai, Z.; Guan, J.; Xiang, Y. Chin. J. Org. Chem. 2013, 33, 2010(in Chinese).
14. [14]
  Mao, Z.; You, H.; Wang, K.; Zhang, Z.; Guan, J.; Dai, Z.; Xiang, Y. Chin. J. Org. Chem. 2015, 35, 2575(in Chinese).
15. [15]
  Deng, M. -M.; Wang, Y. -L.; Zhang, Z. -Y.; Liu, Y.; Wei, B. -L.; Xuan, L. Chin. J. Appl. Chem. 2012, 29, 1093(in Chinese).
16. [16]
  Xie, D. -Y.; Wang, Y.; Wei, H. -W.; Li, X. -M.; Miao, Y. Fin Spec. Chem. 2014, 22, 7(in Chinese).
17. [17]
  Yuan, G. -L.; Zheng, C. -W.; Li, M.; Lv, W. -H.; Zhao, L.; Hua, R. -M. Chem. Reag. 2015, 37, 40(in Chinese).
18. [18]
  Ekke, B. ; Rein, H. ; Hans, K. US 5045229, 1991.
19. [19]
  Shui, M. ; Kazu, M. ; Nori, O. EP 0786509, 1995.
20. [20]
  Kirs, P.; Brem, M.; Taug, A. Angrew. Chem., Int. Ed. 2000, 39, 4216. doi: 10.1002/(ISSN)1521-3773
21. [21]
  Kirsch, P. Modern Fluoroorganic Chemistry-Synthesis, Reactivity, Applications, Wiley-Vch, 2004, pp. 70.
22. [22]
  Zhang, W. -W. Bachelor Thesis, Wuhan Polytechnic University, Wuhan, 2011 (in Chinese).
23. [23]
  Kidwai, M.; Mohan, R. Org. Prep. Proc. 2003, 35, 426. doi: 10.1080/00304940309355855
24. [24]
  Li, S. -Q. M. S. Thesis, East China University of Science and Technology, Shanghai, 2010 (in Chinese).
25. [25]
  You, H. -J. Bachelor thesis, Wuhan Polytechnic University, Wuhan, 2009 (in Chinese).
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