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1. 华东理工大学 化学与分子工程学院 上海,200237
2. 上海天问化学有限公司 上海,200232
收稿日期:2012-12-05,
修回日期:2013-03-08,
纸质出版日期:2013-08-15
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戴修文, 蔡良珍, 闻建勋. 2,3,5,6-全氟亚苯基在液晶分子设计及合成上的应用[J]. 液晶与显示, 2013,28(4): 501-509
DAI Xiu-wen, CAI Liang-zhen, WEN Jian-xun. Applications of 2,3,5,6-Tetrafluorophenylene in Design and Synthesis of Liquid Crystal Molecules[J]. , 2013,28(4): 501-509
戴修文, 蔡良珍, 闻建勋. 2,3,5,6-全氟亚苯基在液晶分子设计及合成上的应用[J]. 液晶与显示, 2013,28(4): 501-509 DOI: 10.3788/YJYXS20132804.0501.
DAI Xiu-wen, CAI Liang-zhen, WEN Jian-xun. Applications of 2,3,5,6-Tetrafluorophenylene in Design and Synthesis of Liquid Crystal Molecules[J]. , 2013,28(4): 501-509 DOI: 10.3788/YJYXS20132804.0501.
设计并合成了两类含氟液晶化合物
分别为4-[(4-苯甲酸2
3
4
5
6-四氟苯基)乙炔基]苯甲酸(4-烷氧基)苯酯和4-[(4-苯甲酸2
3
4
5
6-四氟苯基)乙基]苯甲酸(4-烷氧基)苯酯
前者由于将全氟苯环引入了二苯乙炔结构中
所以具有高双折射率和低的黏度
且耐热性好
可作为自适应光学系统空间光调制器液晶材料;后者引入亚乙基结构使分子的双折射率很小且黏度更低
可作为TFT-LCD混合液晶材料中的减黏部分。两个目标化合物分别是通过sonogashira交叉偶联反应和钯催化加氢还原反应获得。
two kinds of fluorinated liquid crystal compounds were synthesized: 4-n-alkoxyphenyl 4-[4-n-alkoxyphenyl-2
3
4
5
6-tetrafluorophenyl) ethynyl] benzoates and 4-n-alkoxyphenyl 4-[4-n-alkoxyphenyl-2
3
4
5
6-tetrafluorophenyl) ethyl] benzoates.Due to introducing 1
4-perfluorophenylene to molecular structure of diphenyl acetylene in the first compounds
it could be used in adaptive system like as application in construction of spatial light modulator because of the high birfringence
low rotational viscosity and thermal stablility. The liquid crystal compounds with ethylidene bridge could satisfy the requirements of a low viscosity component in TFT-LCD because of the low birfringence and low viscosity. Two target compounds were synthesized by sonogashira reaction and then Pd/C catalytic hydrogenation.
闻建勋,余洪斌,郭志红. 一类新型含氟液晶的合成研究[C]//第六届中国液晶会议文集, 深圳:中国液晶学会,1991.[2] 闻建勋,陈齐,郭志红. 含全氟苯环的液晶化合物及制备方法, 中国专利: CN 92108444.7[P]. 1992-11-25.[3] Wen J X, XuY L,Tian M Q, et al. The synthesis and mesomorphic properties of some nlvel fluoronated ferroelectric liquid crystals [J]. Ferroelectrics, 1993, 148(1):129-138.[4] 黄锡珉. 液晶显示技术的开发和产业化 [J]. 液晶与显示, 2002,17(6):403-415.[5] Pauluth D, Tarumi K. Advanced liquid crystals for television [J]. J. Mater. Chem., 2004, 14(8): 1219-1227.[6] Hird M. Fluorinated liquid crystals-properties and applications [J]. Chem. Soc. Rev., 2007, 36(12):2070-2095.[7] Oh-e M, Kondo K. Electro-optical characteristics and switching behavior of the in-plane switching mode [J]. Appl. Phys. Lett., 1995, 67(26):3895-3897.[8] Pashkovsky E E, Litvina T G. Influence of polymer-molecules on the rotational viscosity and backflow effect at the bend freederiks transition in nematic liquid-crystals [J]. Macromolecules, 1995, 28(6): 1818-1824.[9] Ishinabe T, Miyashita T, Uchida T. Wide-viewing-angle polarizer with a large wavelength range [J]. Jpn. J. Appl. Phys., 2002, 41:4553-4558.[10] 闻建勋,李衡峰. 含氟二苯乙炔类化合物制备方法及用途,中国专利: CN1271712[P].2000-03-24.[11] Xu Y L, Chen Q, Wen J X. Synthesis and mesomorphic properties of the homologous series of 4'-bromophenyl 4"-[4-n-alkoxyphenyl-2,3,4,5,6-tetrafluorophenyl) ethynyl] benzoates [J]. Liq. Cryst., 1993,15: 915-918.[12] Xu Y L, Tian M Q, Hou G, et al. The synthesis and mesomorphic properties of 4'-n-alkoxypheny 4"-[4-n-alkoxyphenyl-2,3,4,5,6-tetrafluorophenyl) ethyl] benzoates[J].Mol Cryst LIq.Cryst.,1996,281:37-42[13] 张然,彭增辉,刘永刚,等. 高低黏度液晶的合成及性能研究 [J]. 液晶与显示, 2009,24(6):789-793.[14] 孙亮,张智勇,游红军,等. 含氟联苯乙炔液晶化合物的合成及其低温性能 [J]. 液晶与显示, 2010,25(6):784-791.[15] Liang X, Lu Y Q, Wu S T, et al. Dual-frequency addressed variable optical attenuator with submilisecond response time [J]. Jpn. J. Appl. Phys., 2005, 44: 1292-1295.[16] Dziaduszek J, Kula P, Dablrowski W, et al. Genral synthesis method of alkyl-alkoxy mult-fluorotolunes for negative high birefringece nemative mixture [J]. Liq. Cryst., 2012, 39:239-247.[17] Read R R, Miller E. Some substituted phenols and their germicidal activity [J]. J.Am. Chem. Soc., 1932, 54: 1195-1199.[18] Zhang Y D, Wen J X. Aconvenient synthesis of fluoro-aromatic acetylene derivatives [J]. J. Fluorine Chem., 1990, 47: 533-535.[19] Zhang Y D, Wen J X. Synthesis of fluoro-diacetylene monomers: 1,4-bis(2,4,6-triayloxy-difluorophenyl)butadiynes [J]. J. Fluorine Chem., 1991, 51:433-437.[20] Balkwill P, Bishop D, Sage I, et al. Fluorination in nematic systems [J]. Mol. Cryst. Liq. Cryst,. 1985, 123:1-13.
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