Regulating the mesogenic properties of imidazolium salts by modifying N3-substituents
详细信息    查看全文
  • 作者:Meng Wang ; Xu Pan ; Jian Chen ; Songyuan Dai
  • 关键词:ionic liquid crystals ; mesogenic properties ; regulate ; N3 ; subsituents
  • 刊名:SCIENCE CHINA Chemistry
  • 出版年:2015
  • 出版时间:December 2015
  • 年:2015
  • 卷:58
  • 期:12
  • 页码:1884-1890
  • 全文大小:838 KB
  • 参考文献:1.Binnemans K. Ionic liquid crystals. Chem Rev, 2005, 105: 4148-204CrossRef
    2.Trilla M, Pleixats R, Parella T, Blanc C, Dieudonne P, Guari Y, Man MWC. Ionic liquid crystals based on mesitylene-containing bis- and trisimidazolium salts. Langmuir, 2008, 24: 259-65CrossRef
    3.Yoshio M, Mukai T, Kanie K, Yoshizawa M, Ohno H, Kato T. Layered ionic liquids: anisotropic ion conduction in new self-organized liquid-crystalline materials. Adv Mater, 2002, 14: 351-54CrossRef
    4.Yoshio M, Mukai T, Kanie K, Yoshizawa M, Ohno H, Kato T. Liquid-crystalline assemblies containing ionic liquids: an approach to anisotropic ionic materials. Chem Lett, 2002: 320-21
    5.Yamanaka N, Kawano R, Kubo W, Masaki N, Kitamura T, Wada Y, Watanabe M, Yanagida S. Dye-sensitized TiO2 solar cells using imidazolium-type ionic liquid crystal systems as effective electrolytes. J Phys Chem B, 2007, 111: 4763-769CrossRef
    6.Pan X, Wang M, Fang XQ, Zhang CN, Huo ZP, Dai SY. Ionic liquid crystal-based electrolyte with enhanced charge transport for dye-sensitized solar cells. Sci China Chem, 2013, 56: 1463-469CrossRef
    7.Lee CK, Huang HW, Lin IJB. Simple amphiphilic liquid crystalline N-alkylimidazolium salts. A new solvent system providing a partially ordered environment. Chem Commun, 2000: 1911-1912
    8.Weiss RG. Liquid-crystalline solvents as mechanistics probes.30. Thermotropic liquid-crystals as reaction media for mechanistic investigations. Tetrahedron, 1988, 44: 3413-475CrossRef
    9.Faul CFJ, Antonietti M. Ionic self-assembly: facile synthesis of supramolecular materials. Adv Mater, 2003, 15: 673-83CrossRef
    10.Bruce DW, Metrangolo P, Meyer F, Prasang C, Resnati G, Terraneo G, Whitwood AC. Mesogenic, trimeric, halogen-bonded complexes from alkoxystilbazoles and 1,4-diiodotetrafluorobenzene. New J Chem, 2008, 32: 477-82CrossRef
    11.Bonhote P, Dias AP, Papageorgiou N, Kalyanasundaram K, Gr?tzel M. Hydrophobic, highly conductive ambient-temperature molten salts. Inorg Chem, 1996, 35: 1168-178CrossRef
    12.Bradley AE, Hardacre C, Holbrey JD, Johnston S, McMath SEJ, Nieuwenhuyzen M. Small-angle X-ray scattering studies of liquid crystalline 1-alkyl-3-methylimidazolium salts. Chem Mater, 2002, 14: 629-35CrossRef
    13.Martin BS, Elena K, Hans-Ullrich S, Birgit C, Peter Fischer WF, Sabine L. Influence of N-alkyl substituents and counterions on the structural and mesomorphic properties of guanidinium salts: experiment and quantum chemical calculations. ChemPhysChem, 2010, 11: 3752-765CrossRef
    14.Zhang QX, Jiao LS, Shan CS, Hou P, Chen B, Xu XY, Niu L. Synthesis and characterisation of novel imidazolium-based ionic liquid crystals with a p-nitroazobenzene moiety. Liq Cryst, 2008, 35: 765-72CrossRef
    15.Dobbs W, Douce L, Allouche L, Louati A, Malbosc F, Welter R. New ionic liquid crystals based on imidazolium salts. New J Chem, 2006, 30: 528-32CrossRef
    16.Gordon CM, Holbrey JD, Kennedy AR, Seddon KR. Ionic liquid crystals: hexafluorophosphate salts. J Mater Chem, 1998, 8: 2627-636CrossRef
    17.Holbrey JD, Seddon KR. The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals. J Chem Soc Dalton Trans, 1999: 2133-2139
    18.Reichert WM, Holbrey JD, Swatloski RP, Gutowski KE, Visser AE, Nieuwenhuyzen M, Seddon KR, Rogers RD. Solid-state analysis of low-melting 1,3-dialkylimidazolium hexafluorophosphate salts (ionic liquids) by combined X-ray crystallographic and computational analyses. Cryst Growth Design, 2007, 7: 1106-114CrossRef
    19.Bowlas CJ, Bruce DW, Seddon KR. Liquid-crystalline ionic liquids. Chem Commun, 1996: 1625-1626
    20.Getsis A, Mudring AV. Imidazolium based ionic liquid crystals: structure, photophysical and thermal behaviour of [Cnmim]Br center dot xH2O (n=12, 14; x=0, 1). Cryst Res Technol, 2008, 43: 1187-196CrossRef
    21.Lee KM, Lee CK, Lin IJB. First example of interdigitated U-shape benzimidazolium ionic liquid crystals. Chem Commun, 1997: 899-900
    22.Lee CK, Peng HH, Lin IJB. Liquid crystals of N,N-dialkylimidazolium salts comprising palladium(II) and copper(II) ions. Chem Mater, 2004, 16: 530-36CrossRef
    23.Wang XJ, Heinemann FW, Yang M, Melcher BU, Fekete M, Mudring AV, Wasserscheid P, Meyer K. A new class of double alkyl-substituted, liquid crystalline imidazolium ionic liquids: a unique combination of structural features, viscosity effects, and thermal properties. Chem Commun, 2009: 7405-7407
    24.Luo SC, Sun SW, Deorukhkar AR, Lu JT, Bhattacharyya A, Lin IJB. Ionic liquids and ionic liquid crystals of vinyl functionalized imidazolium salts. J Mater Chem, 2011, 21: 1866-873CrossRef
    25.Sheldrick GM. SHELXS-97. Program for X-ray crystal structure refinement. Gottingen: University of Gottingen, 1997
    26.Sheldrick GM. SHELXL-97. Program for X-ray crystal structure solution. Gottingen: University of Gottingen, 1997
    27.Fei Z, Kuang D, Zhao D, Klein C, Ang WH, Zakeeruddin SM, Gr?tzel M, Dyson PJ. A Superc
  • 作者单位:Meng Wang (1) (2)
    Xu Pan (2)
    Jian Chen (2)
    Songyuan Dai (2) (3)

    1. Anhui Electric Power Design Institute, Hefei, 230031, China
    2. Key Laboratory of Novel Thin Film Solar Cells, Institute of Plasma Physics, Chinese Academy of Sciences, Hefei, 230031, China
    3. Beijing Key Laboratory of Novel Thin Film Solar Cells, North China Electric Power University, Beijing, 102206, China
  • 刊物类别:Chemistry and Materials Science
  • 刊物主题:Chemistry
    Chinese Library of Science
    Chemistry
  • 出版者:Science China Press, co-published with Springer
  • ISSN:1869-1870
文摘
In this study, a series of imidazolium salts with different N3-substituents (3-position: methyl, vinyl, ethyl, n-propyl, n-butyl)-based ionic-liquid crystals with iodide as counterion (ILCs) are synthesized and characterized, with the aim of regulating the mesogenic properties of imidazolium salts. The imidazolium salts-based ionic-liquid crystals are characterized by thermal analysis, polarized optical microscopy, X-ray powder diffraction, and single-crystalline diffraction. Liquid crystalline phase with a Smectic A phase interdigitated bilayer structure is observed. The mesophase temperature range decreases with the increase of the alkyl chain length of N3-substituent. While when vinyl is attached to the N3 position, intermolecular π-π interactions are formed in adjacent layers, which exert a positive effect on the formation of mesophase. The layer-spacing of imidazolium salts keeps increasing with the increase of the alkyl chain length attached to both the N1 and N3 positions, and gradually decreases with the increasing temperature in liquid crystalline phase. The 1-alkyl-3-vinylimidazolium salt has the smallest layer-spacing, due to the intermolecular π-π interactions between the vinyl and imidazolium rings in adjacent layers. Keywords ionic liquid crystals mesogenic properties regulate N3-subsituents

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700