Citation: Liu Manman, Liu Haohao, Yan Daoren, Zhang Zhiyong, Guan Jintao. Synthesis and Photo-Induced Isomerization Performance for the Novel Bent Diazobenzene Liquid Crystals[J]. Chinese Journal of Organic Chemistry, ;2020, 40(1): 125-132. doi: 10.6023/cjoc201811025 shu

Synthesis and Photo-Induced Isomerization Performance for the Novel Bent Diazobenzene Liquid Crystals

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

Corresponding author: Zhang Zhiyong, zzy6211@126.com
Received Date: 1 March 2019
Revised Date: 8 April 2019
Available Online: 5 January 2019
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(8)

The photo-reversible isomerization property of the azo bend liquid crystal has become a hot topic in the research opt-electronic information materials, but its slow light response has become a key factor restricting its development. At present, the azo bond of the bent liquid crystal compound is far from the central nucleus, and the photo isomerization response time is long, mostly over minutes, which is not conducive to the application research of the photosensitive device. In this work, methyl-1, 3-m-phenylenediamine was chosen the central nucleus. The azo bond is adjacent to both sides of the central ring and the terminal group is an alkyl chain. A series of novel curved bisazo benzene liquid crystal compounds were designed and synthesized, in order to shorten the light response time. The molecular structures of these compounds were identified by IR, ¹H NMR, ¹³C NMR and ICP-MS spectroscopy. The phase transition temperature and phase texture of the liquid crystals were determined by differential scanning calorimeter (DSC) and polarized light microscopy (POM). The photo isomerization performance of 2-methyl-1, 3-bis(4-((4-heptylphenyl)ester)-1-(E)-azophenyl)benzene (2c) was determined by UV-Vis absorption spectroscopy. The photo isomerism and response time of the liquid crystal compound and the doped nematic liquid crystal material were measured by UV-Vis spectrometer and polarizing microscope (POM). The experimental results show that all the curved bisazo benzene liquid crystal compounds designed and synthesized have the smectic phase and the phase temperature range is wide. The photo induced isomerization response time of compound 2c in the liquid crystal state of smectic phase and nematic phase is 2~3 s, and the recovery time of liquid crystal state in sunlight is 3~4 s, which can be reached in diluted ethyl acetate solution for 10 s. This type of bent bisazo liquid crystal compound has a relatively fast photo induced heterogeneous response speed.
- azobenzene,
- curved liquid crystal,
- photoisomerism,
- synthesis
1. [1]
  Rahman, M. L.; Asik, J.; Kumar, S. Liq. Cryst. 2008, 35, 1263. doi: 10.1080/02678290802513808
2. [2]
  Bobrovsky, A.; Shibaev, V.; Hamplová, V. J. Photochem. Photobiol. A:Chem. 2016, 316, 75. doi: 10.1016/j.jphotochem.2015.10.021
3. [3]
  Rahman, M. L.; Asik, J.; Kumar, S.; Tschierske, C. Liq. Cryst. 2008, 35, 1263. doi: 10.1080/02678290802513808
4. [4]
  Nagaveni, N. G.; Roy, A.; Prasad V. J. Mater. Chem. 2012, 22, 8948. doi: 10.1039/c2jm30709j
5. [5]
  Dong, Y. M.S. Thesis, East China University of Science and Technology, Shanghai, 2010(in Chinese).
6. [6]
  Zhou, Y. M.S. Thesis, South China University of Science and Technology, Guangzhou, 2014(in Chinese).
7. [7]
  Rahman, M. L.; Hegde, G.; Yusoff, M. M. New J. Chem. 2013, 37, 2460. doi: 10.1039/c3nj00359k
8. [8]
  Rahman, M. L.; Sarkar, S. M.; Yusoff, M. M. RSC Adv. 2015, 5, 87019. doi: 10.1039/C5RA12705J
9. [9]
  Aralapura, Y. R.; Rahman, M. L.; Yusoff, M. M. Micro Nano Lett. 2017, 12, 201. doi: 10.1049/mnl.2016.0507
10. [10]
  He, W. L.; Li, M.; Liu, S. Q. Liq. Cryst. 2017, 1.
11. [11]
  Duan, J.; Ma, J.; Wu, B. J. Mater. Chem. C 2014, 2, 2375. doi: 10.1039/C3TC32380C
12. [12]
  John, A. A.; Ramil, C. P.; Tian, Y. Org. Lett. 2015, 17, 6258. doi: 10.1021/acs.orglett.5b03268
13. [13]
  Sharma, S.; Han, S. H.; Han, S. Org. Lett. 2015, 17, 2852. doi: 10.1021/acs.orglett.5b01298
14. [14]
  Ding, L.; Xu, M.; Wang, J. Polymer 2014, 55, 1681. doi: 10.1016/j.polymer.2014.02.021
15. [15]
  Mukhopadhyay, R. D.; Praveen, V. K.; Ajayaghosh, A. Mater. Horiz. 2014, 1, 572. doi: 10.1039/C4MH00122B
16. [16]
  Wang, W.; Wang, M. Polym. Bull. 2007, 59, 537. doi: 10.1007/s00289-007-0789-2
17. [17]
  Zheng, H. Y.; Wei, Y. S.; Geng, W. Chem. J. Chin. Univ. 2015, 36, 899(in Chinese).
18. [18]
  Ya, Q.; Dong, X.; Chen, W. Dyes Pigm. 2008, 7, 159.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
3. [3]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
4. [4]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
5. [5]
  Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057
6. [6]
  Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au₂₃(S-Adm)₁₆ and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029
7. [7]
  Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059
8. [8]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
9. [9]
  Yukai Jiang , Yihan Wang , Yunkai Zhang , Yunping Wei , Ying Ma , Na Du . Characterization and Phase Diagram of Surfactant Lyotropic Liquid Crystal. University Chemistry, 2024, 39(4): 114-118. doi: 10.3866/PKU.DXHX202309033
10. [10]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
11. [11]
  Cun WANG , Shaohan XU , Yuqian ZHANG , Yaoyao ZHANG , Tao GONG , Rong WEN , Yuhang LIAO , Yanrong REN . Terbium complex electrochemiluminescent emitters: Synthesis and application in the detection of epinephrine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1351-1360. doi: 10.11862/CJIC.20240427
12. [12]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
13. [13]
  Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
14. [14]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
15. [15]
  Qianping Li , Hua Guan , Changfeng Wan , Yonghai Song , Jianwen Jiang . 大学有机化学复习课项目式教学——以“液晶化合物4-正戊基苯甲酸-4′-正戊基苯酯的合成路线设计与产品制备”为例. University Chemistry, 2025, 40(8): 100-116. doi: 10.12461/PKU.DXHX202410070
16. [16]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
17. [17]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
18. [18]
  Pingwei Wu . Application of Diamond Software in Simplex Teaching. University Chemistry, 2024, 39(3): 118-121. doi: 10.3866/PKU.DXHX202311043
19. [19]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
20. [20]
  Qingying Gao , Tao Luo , Jianyuan Su , Chaofan Yu , Jiazhu Li , Bingfei Yan , Wenzuo Li , Zhen Zhang , Yi Liu . Refinement and Expansion of the Classic Cinnamic Acid Synthesis Experiment. University Chemistry, 2024, 39(5): 243-250. doi: 10.3866/PKU.DXHX202311074

Get Citation

PDF

XML

Metrics

PDF Downloads(20)
Abstract views(2070)
HTML views(548)

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