液晶与显示, 2015, 30 (6): 895, 网络出版: 2016-01-19  

异硫氰基含氟联苯乙炔液晶合成研究

Synthesis of isothiocyanate fluorinated diphenyl acetylene liquid crystal
作者单位
1 武汉轻工大学 化学与环境工程学院,湖北 武汉 430023
2 中国科学院 长春光学精密机械与物理研究所,吉林 长春 130033
摘要
本文合成了4个异硫氰基联苯乙炔类液晶化合物。通过1HNMR、13CNMR、19FNMR、IR和MS谱图鉴定结构正确。用差示扫描热议(DSC)和偏光显微镜(POM)对化合物的相变温度进行了测试,发现所合成目标化合物均呈现向列相,其相变态温度范围在105~137 ℃,其双折射率高于0.47,可作为液晶光栅高双折射率液晶材料的有效组分。
Abstract
This paper has synthesized four isothiocyanato-diphenyl acetylene liquid crystal compounds.Their structures were identified by IR,1HNMR,13CNMR,19FNMR,MS spectra.Their phase transition temperatures were tested by using differential scanning calorimetric(DSC) and polarizing optical microscopy(POM).It is found that all of the new compounds show nematic phase,and their phase transformation temperature was in the range of 105 ℃ to 137 ℃.Their birefringence are more than 0.47,which can be used as the effective components of high birefringence liquid crystal materials of liquid crystal raster.
参考文献

[1] Honma M, Nose T.Liquid-crystal blazed grating with azimuthally distributed liquid-crystal directors[J].Applied Optics, 2004, 43(27): 5193-5197.

[2] 姜文汉.自适应光学技术[J].自然杂志,2005,28(1):7-13.

    Jiang W H.Adaptive optical technology [J].Chinese Journal of Nature, 2005, 28(1): 7-13.(in Chinese)

[3] Jakeman E, Raynes E P.Electro-optic response times in liquid crystals [J].Physics Letters A, 1972, 39(1): 69-70.

[4] 黄翀,王建国,欧阳艳东,等.温度对液晶光阀电光特性的影响[J].光学与光电技术,2008,6(6):33-35.

    Huang C, Wang J G, Ouyang Y D, et al.Influence of temperature on electric-optical performance of liquid crystal light valve [J].Optics & Optoelectronic Technology, 2008, 6(6): 33-35.(in Chinese)

[5] Song Q, Gauza S, Xianyu H Q, et al.High birefringence lateral difluoro phenyl tolane liquid crystals [J].Liquid Crystals, 2010, 37(2): 139-147.

[6] Hird M, Toyne K J, Goodby J W, et al.Synthesis, mesomorphic behaviour and optical anisotropy of some novel materials for nematic mixtures of high birefringence[J].Journal of Materials Chemistry, 2004, 14(11): 1731-1743.

[7] Catanescua C O, Wub S -T, Chien L -C.Tailoring the physical properties of some high birefringence isothiocyanato-based liquid crystals [J].Liquid Crystals, 2004, 31(4): 541-555.

[8] Liao Y M, Janarthanan N,Hsu C -S, et al.Synthesis and mesomorphic properties of fluoro and isothiocyanato biphenyl tolane liquid crystals [J].Liquid Crystals, 2006, 33(10): 1199-1206.

[9] Guan X L, Zhang L Y, Zhang Z L, et al.Synthesis and properties of novel liquid crystalline materials with super high birefringence: styrene monomers bearing diacetylenes, naphthyl and nitrogen-containing groups [J].Tetrahedron, 2009, 65(18): 3728-3732.

[10] Niori T, Sekine T, Watanabe, et al.Distinct ferroelectric smectic liquid crystals consisting of banana shaped achiral molecules [J].Journal of Materials Chemistry, 1996, 6(7): 1231-1233.

[11] Marashall J A, Yanik M M, Adams N D, et al.Generation of nonracemic 2-(t-butyldimethylsilyloxy)-3-butynyllithium from (S)-ethyl lactate: [(S)-4-(t-butyldimethylsilyloxy)-2-pentyn-1-OL][J].Organic Syntheses, 2005, 81: 157.

[12] 张智勇,刘可庆,戴志群,等.高双折射液晶化合物的研究进展[J].液晶与显示,2014,29(6):873-880.

    Zhang Z Y, Liu K Q, Dai Z Q, et al.Research progress of high birefringence liquid crystal compounds [J].Chinese Journal of Liquid Crystals and Displays, 2012, 29(6): 873-880.(in Chinese)

[13] Bhadury P S, Palit M, Sharma M, et al.Fluorinated phosphonium ylides: versatile in situ wittig intermediates in the synthesis of hydrofluorocarbons [J].Journal of Fluorine Chemistry, 2002, 116(1): 75-80.

[14] Huff B E, Koenig M, Mitchell D, et al.Synthesis of unsymmetrical biaryls using a modified Suzuki cross-coupling: 4-biphenylcarboxaldehyde [1,1′-Biphenyl]-4-carboxaldehyde [J].Organic Syntheses, 2004, 10: 102.

[15] Li Z H, Wong M S.Synthesis and functional properties of end-dendronized oligo (9, 9-diphenyl) fluorenes [J].Organic Letters, 2006, 8(7): 1499-1502.

[16] 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.

    Sun L, Zhang Z Y, You H J, et al.Synthesis and low-temperature properties of lateral difluoro-diphenyltolane compounds[J].Chinese Journal of Liquid Crystals and Displays, 2010, 25(6): 784-791.(in Chinese)

[17] 黄江涛.二氟乙烯基氟二苯乙炔类液晶的合成与性能研究[D].武汉:武汉轻工大学,2013.

    Huang J T.Synthesis and properties of difluorovinyl fluorinated tolane liquid crystal compounds[D].Wuhan: Wuhan Polytechnic University, 2013.(in Chinese)

[18] Catanescu O, Chien L C.High birefringence difluoroisothiocyanate biphenyl tolane liquid crystals[J].Liquid Crystals, 2006, 33(1): 115-120.

[19] Miyaura N, Yamada K, Suginome H, et al.Novel and convenient method for the stereo- and regiospecific synthesis of conjugated alkadienes and alkenynes via the palladium-catalyzed cross-coupling reaction of 1-alkenylboranes with bromoalkenes and bromoalkynes [J].Journal of the American Chemical Society, 1985, 107(4): 972-980.

[20] Sonogashira K.Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides [J].Journal of Organometallic Chemistry, 2002, 653(1/2): 46-49.

[21] Dunmur D A, Fukuda A, Luckhurst G R.Physical Properties of Liquid Crystals: Nematics [M].London: Institution of Engineering and Technology, 2001: 515-517.

[22] 宣丽,彭增辉,刘永刚,等.用于液晶波前校正器的快速液晶材料分子设计与混配:中国,CN103725294A[P].2013-12-19.

    Xuan L, Peng Z H, Liu Y G, et al.Design and mixed for fast liquid crystal material molecules of liquid crystal front wave corrector:China,CN103725294A[P].2013-12-19.(in Chinese)

刘胜, 申烦, 黄江涛, 张智勇, 戴志群, 彭增辉. 异硫氰基含氟联苯乙炔液晶合成研究[J]. 液晶与显示, 2015, 30(6): 895. LIU Sheng, SHEN Fan, HUANG Jiang-tao, ZHANG Zhi-yong, DAI Zhi-qun, PENG Zeng-hui. Synthesis of isothiocyanate fluorinated diphenyl acetylene liquid crystal[J]. Chinese Journal of Liquid Crystals and Displays, 2015, 30(6): 895.

关于本站 Cookie 的使用提示

中国光学期刊网使用基于 cookie 的技术来更好地为您提供各项服务,点击此处了解我们的隐私策略。 如您需继续使用本网站,请您授权我们使用本地 cookie 来保存部分信息。
全站搜索
您最值得信赖的光电行业旗舰网络服务平台!