Citation: Md Lutfor Rahman, Gurumuthy Hegde, Shaheen M. Sarkar, Mashitah Mohd Yusoff. Synthesis and photoswitching properties of azobenzene liquid crystals with a pentafluorobenzene terminal[J]. Chinese Chemical Letters, ;2014, 25(12): 1611-1614. doi: 10.1016/j.cclet.2014.06.025 shu

Synthesis and photoswitching properties of azobenzene liquid crystals with a pentafluorobenzene terminal

1.
Faculty of Industrial Sciences & Technology, Universiti Malaysia Pahang, Kuantan 26300, Malaysia

Corresponding author: Md Lutfor Rahman,
Received Date: 24 February 2014
Available Online: 12 June 2014
Fund Project: This research was supported by UMP Research (No. RDU 100338) (No. RDU 100338)also RAGS (No. RDU131408). (No. RDU131408)

The fluorine-substituted benzoate ester rod-shaped liquid crystals containing an azobenzene side chain linked with terminal double bonds were synthesized and characterized. The mesophase and photoswitching properties were determined by polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and UV-visible spectrometry. The rod-shaped compound 4a having an odd number of carbon atoms in the alkyl chains exhibits nematic phase and SmA type phase whereas compound 4b having an even number of carbon atoms showed only nematic phase. Both fluorinecontaining compounds 4c and 4d showed only SmA type phases. The photoswitching properties of these compounds showed a rate of trans to cis isomerization ranging 19-20 s, whereas reverse process took around 230 min in solution. These materials may be ideal in the field of optically rewritable applications where both on and off rates should be crucial.
- Liquid crystals,
- Azobenzene,
- Photoswitching,
- Fluorine compounds
1. [1]
  [1] J. Tao, J. Zhong, P. Liu, S. Daniels, Z. Zeng, Pyridinium-based ionic liquid crystals with terminal fluorinated pyrrolidine, J. Fluor. Chem. 144 (2012) 73-78.
2. [2]
  [2] M.L. Rahman, G. Hegde, M.M. Yusoff, et al., New pyrimidine-based photo-switchable bent-core liquid crystals, N. J. Chem. 37 (2013) 2460-2467.
3. [3]
  [3] M. Hird, Fluorinated liquid crystals -properties and applications, Chem. Soc. Rev. 36 (2007) 2070-2095.
4. [4]
  [4] D. Demus, Y. Goto, S. Sawada, et al., Trifluorinated liquid crystals for TFT displays, Mol. Cryst. Liq. Cryst. 260 (1995) 1-21.
5. [5]
  [5] (a) S.K. Prasad, G. Nair, G. Hegde, Dynamic self-assembly of the liquid-crystalline smectic A phase, Adv. Mater. 17 (2005) 2086-2091; (b) S.T. Ha, K.L. Foo, H.C. Lin, et al., Mesomorphic behavior of new benzothiazole liquid crystals having Schiff base linker and terminal methyl group, Chin. Chem. Lett. 23 (2012) 761-764.
6. [6]
  [6] L.M. Blinov, Photoinduced molecular reorientation in polymers, Langmuir-Blodgett films and liquid crystals, J. Nonlinear Opt. Phys. Mater. 5 (1996) 165-187.
7. [7]
  [7] T. Ikeda, I. Tsutsumi, Optical switching and image storage by means of azobenzene liquid-crystal films, Science 268 (1995) 1873-1875.
8. [8]
  [8] S.K. Prasad, G. Nair, G. Hegde, Nonequilibrium liquid crystalline layered phase stabilized by light, J. Phys. Chem. B 111 (2007) 345-350.
9. [9]
  [9] M.L. Rahman, G. Hegde, M. Azazpour, M.M. Yusoff, S. Kumar, Synthesis and characterization of liquid crystalline azobenzene chromophores with fluorobenzene terminal, J. Fluor. Chem. 156 (2013) 230-235.
10. [10]
  [10] M.L. Rahman, G. Hegde, S. Kumar, C. Tschierke, V.G. Chigrinov, Synthesis and characterization of bent-shaped azobenzene monomers: guest-host effects in liquid crystals with azo dyes for optical image storage devices, Opt. Mater. 32 (2009) 176-183.
11. [11]
  [11] N.G. Nagaveni, A. Roy, V. Prasad, Achiral bent-core azo compounds: effect of different types of linkage groups and their direction of linking on liquid crystalline properties, J. Mater. Chem. 22 (2012) 8948-8959.
12. [12]
  [12] G.G. Nair, S.K. Prasad, C.V. Yelamaggad, Opto-dielectric effect on a nematic liquid crystal doped with a photoactive azo mesogen, J. Appl. Phys. 87 (2000) 2084-2089.
13. [13]
  [13] T. Sasaki, T. Ikeda, K. Ichimura, Photoisomerization and thermal isomerization behavior of azobenzene derivatives in liquid crystalline polymer matrices, Macromolecules 26 (1993) 151-154.
1. [1]
  Kai Ye , Zhicheng Ye , Chuantao Wang , Zhilai Luo , Cheng Lian , Chunyan Bao . Artificial signal transduction triggered by molecular photoisomerization in lipid membranes. Chinese Chemical Letters, 2025, 36(4): 110033-. doi: 10.1016/j.cclet.2024.110033
2. [2]
  Xiang Wang , Qingping Song , Zixiang He , Gong Zhang , Tengfei Miao , Xiaoxiao Cheng , Wei Zhang . Constructing diverse switchable circularly polarized luminescence via a single azobenzene polymer film. Chinese Chemical Letters, 2025, 36(1): 110047-. doi: 10.1016/j.cclet.2024.110047
3. [3]
  Qian Wang , Yeping Bian , Gagan Dhawan , Wei Zhang , Alexander E. Sorochinsky , Ata Makarem , Vadim A. Soloshonok , Jianlin Han . FDA approved fluorine-containing drugs in 2023. Chinese Chemical Letters, 2024, 35(11): 109780-. doi: 10.1016/j.cclet.2024.109780
4. [4]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
5. [5]
  Wei Sun , Anjing Liao , Li Lei , Xu Tang , Ya Wang , Jian Wu . Research progress on piperidine-containing compounds as agrochemicals. Chinese Chemical Letters, 2025, 36(1): 109855-. doi: 10.1016/j.cclet.2024.109855
6. [6]
  Xinlong Han , Huiying Zeng , Chao-Jun Li . Trifluoromethylative homo-coupling of carbonyl compounds. Chinese Chemical Letters, 2025, 36(1): 109817-. doi: 10.1016/j.cclet.2024.109817
7. [7]
  Tong Zhang , Xiaojing Liang , Licheng Wang , Shuai Wang , Xiaoxiao Liu , Yong Guo . An ionic liquid assisted hydrogel functionalized silica stationary phase for mixed-mode liquid chromatography. Chinese Chemical Letters, 2025, 36(1): 109889-. doi: 10.1016/j.cclet.2024.109889
8. [8]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
9. [9]
  Yu-Yu Tan , Lin-Heng He , Wei-Min He . Copper-mediated assembly of SO₂F group via radical fluorine-atom transfer strategy. Chinese Chemical Letters, 2024, 35(9): 109986-. doi: 10.1016/j.cclet.2024.109986
10. [10]
  Jia-Ru Li , Ning Li , Li-Ling He , Jun He . Fluorine-functionalized zirconium-organic cages for efficient photocatalytic oxidation of thioanisole. Chinese Chemical Letters, 2025, 36(1): 109934-. doi: 10.1016/j.cclet.2024.109934
11. [11]
  Xin Dong , Jing Liang , Zhijin Xu , Huajie Wu , Lei Wang , Shihai You , Junhua Luo , Lina Li . Exploring centimeter-sized crystals of bismuth-iodide perovskite toward highly sensitive X-ray detection. Chinese Chemical Letters, 2024, 35(6): 108708-. doi: 10.1016/j.cclet.2023.108708
12. [12]
  Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
13. [13]
  Jiajing Wu , Ru-Ling Tang , Sheng-Ping Guo . Three types of promising functional building units for designing metal halide nonlinear optical crystals. Chinese Journal of Structural Chemistry, 2024, 43(6): 100291-100291. doi: 10.1016/j.cjsc.2024.100291
14. [14]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
15. [15]
  Zhenyang Lin . A classification scheme for inorganic cluster compounds based on their electronic structures and bonding characteristics. Chinese Journal of Structural Chemistry, 2024, 43(5): 100254-100254. doi: 10.1016/j.cjsc.2024.100254
16. [16]
  Yin-Hang Chai , Li-Long Dang . New structural breakthrough and topological transformation of homogeneous metalla[4]catenane compounds. Chinese Journal of Structural Chemistry, 2024, 43(10): 100322-100322. doi: 10.1016/j.cjsc.2024.100322
17. [17]
  Hongxia Li , Xiyang Wang , Du Qiao , Jiahao Li , Weiping Zhu , Honglin Li . Mechanism of nanoparticle aggregation in gas-liquid microfluidic mixing. Chinese Chemical Letters, 2024, 35(4): 108747-. doi: 10.1016/j.cclet.2023.108747
18. [18]
  Jie Wu , Xiaoqing Yu , Guoxing Li , Su Chen . Engineering particles towards 3D supraballs-based passive cooling via grafting CDs onto colloidal photonic crystals. Chinese Chemical Letters, 2024, 35(4): 109234-. doi: 10.1016/j.cclet.2023.109234
19. [19]
  Jingyu Chen , Sha Wu , Yuhao Wang , Jiong Zhou . Near-perfect separation of alicyclic ketones and alicyclic alcohols by nonporous adaptive crystals of perethylated pillar[5]arene and pillar[6]arene. Chinese Chemical Letters, 2025, 36(4): 110102-. doi: 10.1016/j.cclet.2024.110102
20. [20]
  Ziyi Liu , Feifei Guo , Tingting Cao , Youxuan Sun , Xutang Tao , Zeliang Gao . High thermal conductivity in Ga2TeO6 crystals: Synergistic effects of rigid polyhedral frameworks and stereochemically inert cations. Chinese Journal of Structural Chemistry, 2025, 44(4): 100544-100544. doi: 10.1016/j.cjsc.2025.100544

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(605)
HTML views(14)

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