Citation: Yu-Zhen Zhao, Dong Wang, Ze-Min He, Gang Chen, Lan-Ying Zhang, Hai-Quan Zhang, Huai Yang. Naphthylethyne based liquid crystals with high birefringence and characteristics of selective reflection[J]. Chinese Chemical Letters, ;2015, 26(6): 785-789. doi: 10.1016/j.cclet.2015.03.023 shu

Naphthylethyne based liquid crystals with high birefringence and characteristics of selective reflection

1.
a State Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, China;
2.
b Department of Materials Science and Engineering, College of Engineering, Peking University, Beijing 100871, China;
3.
c Department of Materials Physics and Chemistry, University of Science and Technology Beijing, Beijing 100083, China

Corresponding author: Hai-Quan Zhang, Huai Yang,
Received Date: 14 January 2015
Available Online: 12 March 2015
Fund Project: the National Science Foundation of China (No. 51173155) (No. 2013DFB50340) the Major Project of Beijing Science & Technology Program (No. Z121100006512002) (No. 51173155) the National Natural Science Foundation of China (No. 51103010) (No. Z121100006512002) and the Doctoral Fund of Chinese Ministry of Education (No. 20120001130005). (No. 51103010)

A series of high birefringence liquid crystalline molecules with cyano, isothiocyanato and trifluoromethyl terminal compounds based on naphthylethyne core was successfully synthesized and characterized. The molecular structures of the intermediates and resulting compounds were confirmed by Fourier transform infrared (FT-IR), nuclear magnetic resonance (NMR), mass spectrometry (MS), and elemental analysis (EA). Their thermal stability, transition temperatures, and phase sequences were investigated by simultaneous thermal analyzer polarized (STA), optical microscopy (POM) and differential scanning calorimetry (DSC). The birefringence was measured by using an Abbe refractometer. In addition, the selective reflection characteristics with naphthylethyne compounds were also studied.
- Liquid crystal,
- Naphthylethyne,
- Birefringence,
- Selective reflection
1. [1]
  [1] W.L. He, T. Liu, Z. Yang, et al., Facile synthesis and characterization of novel thermo-chromism cholesteryl-containing hydrogen-bonded liquid crystals, Chin. Chem. Lett. 20 (2009) 1303-1306.
2. [2]
  [2] D.W. Zhang, W. Huang, G.H. Pan, et al., Synthesis and characterization of nonsymmetrical liquid crystals containing a cholesteryl ester moiety, Chin. Chem. Lett. 20 (2009) 562-565.
3. [3]
  [3] D.Y. Zhao, Q.Y. Meng, X.P. Cui, H. Yang, Synthesis and mesomorphic properties of novel tolane-type liquid crystals, Chin. Chem. Lett. 20 (2009) 1283-1286.
4. [4]
  [4] H.Q. Zhang, A.L. Qin, Tuning the helical twisting power of nematic liquid crystals induced by chiral 1,2-propanediol derivatives using varied substituents, Chin. Chem. Lett. 23 (2012) 37-40.
5. [5]
  [5] K.G. Liu, H.F. Li, K. Wang, J.X. Wen, Synthesis and characterization of novel fluorinated bistolane-type liquid crystals, Liq. Cryst. 28 (2001) 1463-1467.
6. [6]
  [6] C. Sekine, K. Iwakura, N. Konya, M. Minai, K. Fujisawa, Synthesis and properties of some novel high birefringence phenylacetylene liquid crystal materials with lateral substituents, Liq. Cryst. 28 (2001) 1375-1387.
7. [7]
  [7] C. Sekine, N. Konya, M. Minai, K. Fujisawa, Synthesis and properties of high birefringence liquid crystals: thiophenylacetylene and benzothiazolylacetylene derivatives, Liq. Cryst. 28 (2001) 1361-1367.
8. [8]
  [8] L.Y. Zhang, X.L. Guan, Z.L. Zhang, et al., Preparation and properties of highly birefringent liquid crystalline materials: styrene monomers with acetylenes, naphthyl, and isothiocyanate groups, Liq. Cryst. 37 (2010) 453-462.
9. [9]
  [9] D.K. Yang, J.W. Doane, Z. Yaniv, J. Glasser, Cholesteric reflective display: drive scheme and contrast, Appl. Phys. Lett. 64 (1994) 1905-1907.
10. [10]
  [10] R.L. Sutherland, L.V. Natarajan, V.P. Tondiglia, T.J. Bunning, Bragg gratings in an acrylate polymer consisting of periodic polymer-dispersed liquid-crystal planes, Chem. Mater. 5 (1993) 1533-1538.
11. [11]
  [11] C.C. Bowler, H.J. Yuan, G.P. Crawford, Morphology of holographically-formed polymer dispersed liquid crystals (H-PDLC), Mol. Cryst. Liq. Cryst. 331 (1999) 209-216.
12. [12]
  [12] X.L. Guan, L.Y. Zhang, Z.L. Zhang, et al., Synthesis and properties of novel liquid crystalline materials with super high birefringence: styrene monomers bearing diacetylenes, naphthyl, and nitrogen-containing groups, Tetrahedron 65 (2009) 3728-3732.
13. [13]
  [13] K. Okano, A. Shishido, O. Tsutsumi, T. Shiono, T. Ikeda, Highly birefringent liquidcrystalline polymers for photonic applications: synthesis of liquid-crystalline polymers with side-chain azo-tolane mesogens and their holographic properties, J. Mater. Chem. 15 (2005) 3395-3401.
14. [14]
  [14] M. Hird, K.J. Toyne, J.W. Goodby, et al., Synthesis, mesomorphic behaviour and optical anisotropy of some novel materials for nematic mixtures of high birefringence, J. Mater. Chem. 14 (2004) 1731-1743.
15. [15]
  [15] K. Okano, O. Tsutsumi, A. Shishido, T. Ikeda, Azotolane liquid-crystalline polymers: huge change in birefringence by photoinduced alignment change, J. Am. Chem. Soc. 128 (2006) 15368-15369.
16. [16]
  [16] C.M. Hudson, R.A. Shenoy, M.E. Neubert, R.G. Peischek, Synthesis and mesomorphic properties of some asymmetrical pyrimidinylphenyldiacetylenes, Liq. Cryst. 26 (1999) 241-250.
17. [17]
  [17] A.J. Seed, K.J. Toyne, J.W. Goodby, M. Hird, Synthesis, transition temperatures, and optical properties of various 2,6-disubstituted naphthalenes and related 1-benzothiophenes with butylsulfanyl and cyano or isothiocyanato terminal groups, J. Mater. Chem. 10 (2000) 2069-2080.
18. [18]
  [18] Y. Arakawa, S. Nakajima, S.M. Kang, et al., Synthesis and evaluation of dinaphthylacetylene nematic liquid crystals for high-birefringence materials, Liq. Cryst. 39 (2012) 1063-1069.
19. [19]
  [19] Z.Y. Bian, K.X. Li, W. Huang, et al., Characteristics of selective reflection of chiral nematic liquid crystalline gels with a nonuniform pitch distribution, Appl. Phys. Lett. 91 (2007) 201908.
20. [20]
  [20] Z.C. Miao, D. Wang, Y.M. Zhang, et al., Asymmetrical phenyldiacetylenes liquid crystalline compounds with high birefringence and characteristics of selective reflection, Liq. Cryst. 39 (2012) 1291-1296.
1. [1]
  Ziqi Chen , Miriding Mutailipu . Achieving the birefringence-bandgap trade-off: hydrogen-bond engineered biuret-cyanurate. Chinese Journal of Structural Chemistry, 2025, 44(10): 100695-100695. doi: 10.1016/j.cjsc.2025.100695
2. [2]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
3. [3]
  Yi-Chang Yang , Rui-Xi Wang , Li-Ming Wu , Ling Chen . Regulating the coplanarity of π-conjugated units through hydrogen bonding in FAHC2O4 and FAH2C3N3S3 crystals. Chinese Journal of Structural Chemistry, 2025, 44(10): 100714-100714. doi: 10.1016/j.cjsc.2025.100714
4. [4]
  Peng-Fei Li , Chun-Li Hu , Bo Zhang , Jiang-Gao Mao , Fang Kong . From HgGa₂(SeO₃)₄ to Hg₂Ga(SeO₃)₂F: The first Hg^Ⅰ-based selenite birefringent crystal triggered by linear groups and fluoride ions. Chinese Chemical Letters, 2026, 37(2): 110588-. doi: 10.1016/j.cclet.2024.110588
5. [5]
  Yu Zhou , Lin-Tao Jiang , Xiao-Ming Jiang , Bin-Wen Liu , Guo-Cong Guo . Mixed-anion square-pyramid [SbS₃I₂] units causing strong second-harmonic generation intensity and large birefringence. Chinese Chemical Letters, 2025, 36(4): 109740-. doi: 10.1016/j.cclet.2024.109740
6. [6]
  Hongyuan Sha , Dongling Yang , Yanran Shang , Zujian Wang , Rongbing Su , Chao He , Xiaoming Yang , Xifa Long . Trithionic guanidine: A novel semi-organic short-wave ultraviolet nonlinear optical sulfate with dimeric heteroleptic tetrahedra. Chinese Chemical Letters, 2025, 36(4): 109730-. doi: 10.1016/j.cclet.2024.109730
7. [7]
  Weiping Guo , Ying Zhu , Hong-Hua Cui , Lingyun Li , Yan Yu , Zhong-Zhen Luo , Zhigang Zou . β-Pb₃P₂S₈: A new optical crystal with exceptional birefringence effect. Chinese Chemical Letters, 2025, 36(2): 110256-. doi: 10.1016/j.cclet.2024.110256
8. [8]
  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
9. [9]
  Yang Li , Yihan Chen , Jiaxin Luo , Qihuan Li , Yiwu Quan , Yixiang Cheng . Enhanced circularly polarized luminescence emission promoted by achiral dichroic oligomers of F8BT in cholesteric liquid crystal. Chinese Chemical Letters, 2024, 35(11): 109864-. doi: 10.1016/j.cclet.2024.109864
10. [10]
  Jia-Xin Wu , Zheng Yin , Ming-Hua Zeng . Multi-phase evolution of MOFs involving crystal, liquid and glass: new dynamic chemistry. Chinese Journal of Structural Chemistry, 2025, 44(10): 100710-100710. doi: 10.1016/j.cjsc.2025.100710
11. [11]
  Qiuting Zhang , Fan Wu , Jin Liu , Hang Su , Yanhui Zhong , Zian Lin . Facile synthesis of single-crystal 3D covalent organic frameworks as stationary phases for high-performance liquid chromatographic separation. Chinese Chemical Letters, 2025, 36(8): 110649-. doi: 10.1016/j.cclet.2024.110649
12. [12]
  Qin Wang , Han Luo , Luli Wang , Ling Huang , Liling Cao , Xuehua Dong , Guohong Zou . KSb₂F₇·2KNO₃: Unveiling the peak birefringence in inorganic antimony oxysalts. Chinese Chemical Letters, 2025, 36(7): 110173-. doi: 10.1016/j.cclet.2024.110173
13. [13]
  Miao-Bin Xu , Qian-Qian Chen , Bing-Xuan Li , Ke-Zhao Du , Jin Chen . π-Lone pair synergy in (C₇H₄NO₄)(IO₃): Optimal balance among SHG, birefringence, and bandgap performance. Chinese Chemical Letters, 2025, 36(11): 110513-. doi: 10.1016/j.cclet.2024.110513
14. [14]
  Li-Ying Wang , Jun-Jie Yu , Shuai Wang , Yang Liu , Ke-Xian Song , Ji-Pan Yu , Li-Yong Yuan , Zhi-Rong Liu , Wei-Qun Shi . Pyridine-based ionic sp² carbon-conjugated covalent organic frameworks for selective extraction of Pu(Ⅳ) from high-level liquid waste. Chinese Chemical Letters, 2025, 36(8): 110706-. doi: 10.1016/j.cclet.2024.110706
15. [15]
  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
16. [16]
  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
17. [17]
  Liming Li , Yanchang Liu , Peng Kang , Donghui Feng , Yuguang Zhang , Hangxing Ren , Jianrong Zeng , He Zhu , Qiang Li , Xiaoya Cui . Scalable and rapid liquid synthesis of PtNi electrocatalyst for hydrogen evolution reaction. Chinese Chemical Letters, 2026, 37(2): 112022-. doi: 10.1016/j.cclet.2025.112022
18. [18]
  Jiakun Bai , Junhui Jia , Aisen Li . An elastic organic crystal with piezochromic luminescent behavior. Chinese Journal of Structural Chemistry, 2024, 43(6): 100323-100323. doi: 10.1016/j.cjsc.2024.100323
19. [19]
  Kezhen Qi , Shu-yuan Liu , Ruchun Li . Selective dissolution for stabilizing solid electrolyte interphase. Chinese Chemical Letters, 2024, 35(5): 109460-. doi: 10.1016/j.cclet.2023.109460
20. [20]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1233)
HTML views(22)

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