Thermotropic ionic liquid crystals

Materials

Volumn 4, Issue 1, 2010, Pages 206-259

  Axenov, Kirill V ^a   Laschat, Sabine ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Ionic thermotropic mesogens; Liquid crystals; Metallomesogens

Indexed keywords

IONIC POLYMER; IONIC THERMOTROPIC MESOGEN; LIQUID-CRYSTALS; MESOGENS; MESOMORPHIC PROPERTY; METALLOMESOGENS; ORGANICS; THERMOTROPIC IONIC LIQUID CRYSTALS; THERMOTROPIC MESOGENS;

IONIC LIQUIDS;

EID: 80052680700     PISSN: None     EISSN: 19961944     Source Type: Journal    
DOI: 10.3390/ma4010206     Document Type: Review

References (198)

1. Goodby, J.W.; Gray, G.W. Handbook of Liquid Crystals, 1st ed.; Demus, D., Goodby, J., Gray, G.W., Spiess, H.-W., Vill, V., Eds.; Wiley-VCH: Weinheim, Germany; New York, NY, USA, 1998; Volume 1, Chapter 2, pp. 18-19.
2. Electro-Optical Displays, 1st ed.; Karim, M.A., Ed.; Marcel Dekker, Inc.: New York, NY, USA, 1992.
3. Clark, N.A.; Johnson, K.M. Liquid Crystal-Applications and Uses, 1st ed.; Bahadur, B., Ed.; World Scientific: Singapore, 1992; Volume 3, Chapter 17, pp. 209-252.
4. De Bougrenet de la Tocnaye, J.L. Engineering liquid crystals for optimal uses in optical communication systems. Liq. Cryst. 2004, 31, 241-269.
5. Hussain, A.; Pina, A.S.; Roque, A.C.A. Bio-recognition and detection using liquid crystals. Bisens. Bioelectron. 2009, 25, 1-8.
6. Ohm, C.; Brehmer, M.; Zentel, R. Liquid crystalline elastomers as actuators and sensors. Adv. Mater. 2010, 22, 3366-3387.
7. Goodby, J.W.; Gray, G.W. Handbook of Liquid Crystals, 1st ed.; Demus, D., Goodby, J., Gray, G.W., Spiess, H.-W., Vill, V., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Volume 1-4.
8. Paleos, C.M. Thermotropic liquid crystals derived from amphiphilic mesogens. Mol. Cryst. Liq. Cryst. 1994, 243, 159-183.
9. Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev. 1999, 99, 2071-2083.
10. Yoshio, M.; Mukai, T.; Ohno, H.; Kato, T. One-dimensional ion transport in self-organized columnar ionic liquids. J. Am. Chem. Soc. 2004, 126, 994-995.
11. Binnemans, K. Ionic liquid crystals. Chem. Rev. 2005, 105, 4148-4204.
12. Bradley, A.E.; Hardacre, C.; Holbrey, J.D.; Johnston, S.; McMath, S.E.J.; Nieuwenhuyzen, M. Small-angle X-ray scattering studies of liquid crystalline 1-alkyl-3-methylimidazolium salts. Chem. Mater. 2002, 14, 629-635.
13. Ujiie, S.; IImura, K. Ammonium halide type thermotropic liquid-crystalline polyethylenimines and those low-mass model compounds. Chem. Lett. 1990, 19, 995-998.
14. Motoyanagi, J.; Fukushima, T.; Aida, T. Discotic liquid crystals stabilized by interionic interactions: Imidazolium ion-anchored paraffinic triphenylene. Chem. Commun. 2005, 101-103, DOI:10.1039/B414649B.
15. Ujiie, S.; Iimura, K. Thermal properties and orientational behavior of a liquid-crystalline ion complex polymer. Macromolecules 1992, 25, 3174-3178.
16. Goodby, J.W. Handbook of Liquid Crystals, 1st ed.; Demus, D., Goodby, J., Gray, G.W., Spiess, H.-W., Vill, V., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Volume 2A, Chapter 1, pp. 3-18.
17. Chandrasekhar, S. Handbook of Liquid Crystals, 1st ed.; Demus, D., Goodby, J., Gray, G.W., Spiess, H.-W., Vill, V., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Volume 2B, Chapter 8, pp. 750-752.
18. Yu, W.; Peng, H.; Zhang, H.; Zhou, X. Synthesis and mesophase behaviour of morpholinium ionic liquid crystals. Chin. J. Chem. 2009, 27, 1471-1475.
19. Kondrat, S.; Bier, M.; Harnau, L. Phase behavior of ionic liquid crystals. J. Chem Phys. 2010, 132, 184901:1-184901:10.
20. Fairhurst, C.E.; Fuller, S.; Gray, J.; Holmes, M.C.; Tiddy, G.J.T. Handbook of Liquid Crystals, 1st ed.; Demus, D., Goodby, J., Gray, G.W., Spiess, H.-W., Vill, V., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Volume 3, Chapter 7, pp. 341-392.
21. Busico, V.; Cernicchiarro, P.; Corradini, P.; Vacatello, M. Polymorphism in anhydrous amphiphilic systems. Long-chain primary n-alkylammonium chlorides. J. Phys. Chem. 1983, 87, 1631-1635.
22. Menschutkin, N. Affinity coefficients of alkyl halogen compounds and of amines. Z. Phys. Chem. 1890, 6, 41-57.
23. T. Liq. Cryst. 1993, 13, 201-212.
24. Ohta, K.; Sugiyama, T.; Nogami, T. A Smectic T Phase of 1,4-dialkyl-1,4-diazoniabicyclo-[2.2.2]octane dibromides. J. Mater. Chem. 2000, 10, 613-616.
25. Nikokavoura, A.; Tsiourvas, D.; Arkas, M.; Sideratou, Z.; Paleos, C.M. Thermotropic liquid crystalline behaviour of piperazinium and homopiperazinium alkylsulphates. Liq. Cryst. 2002, 29, 1547-1553.
26. Goossens, K.; Lava, K.; Nockemann, P.; Van Hecke, K.; Van Meervelt, L.; Driesen, K.; Görller-Walrand, C.; Binnemans, K.; Cardinaels, T. Pyrrolidinium ionic liquid crystals. Chem. Eur. J. 2009, 15, 656-674.
27. Goossens, K.; Lava, K.; Nockemann, P.; Van Hecke, K.; Van Meervelt, L.; Pattison, P.; Binnemans, K.; Cardinaels, T. Pyrrolidinium ionic liquid crystals with pendant mesogenic groups. Langmuir 2009, 25, 5881-5897.
28. Getsis, A.; Mudring, A.-V. Structural and thermal behaviour of the pyrrolidinium based ionic liquid crystals [C10mpyr]Br and [C12mpyr]Br. Z. Anorg. Allg. Chem. 2009, 635, 2214-2221.
29. Lava, K.; Binnemans, K.; Cardinaels, T. Piperidinium. piperazinium and morpholinium ionic liquid crystals. J. Phys. Chem. B 2009, 113, 9506-9511.
30. Li, W.; Zhang, J.; Li, B.; Zhang, M.; Wu, L. Branched quaternary ammonium amphiphiles: Nematic ionic liquid crystals near room temperature. Chem. Commun. 2009, 35, 5269-5271.
31. Bradaric, C.J.; Downard, A.; Kennedy, C.; Robertson, A.J.; Zhou, Y. Industrial preparation of phosphonium ionic liquids. Green Chem. 2003, 5, 143-152.
32. Henderson, W.A., Jr; Streuli, C.A. The basicity of phosphines. J. Am. Chem. Soc. 1960, 82, 5791-5794.
33. Henderson, W.A., Jr; Buckler, S.A. The nucleophilicity of phosphines. J. Am. Chem. Soc. 1960, 82, 5794-5800.
34. Abdallah, D.J.; Robertson, A.; Hsu, H.-F.; Weiss, R.G. Smectic liquid-crystalline phases of quaternary group Va (especially phosphonium) salts with three equivalent long n-alkyl chains. How do layered assemblies form in liquid-crystalline and crystalline phases? J. Am. Chem. Soc. 2000, 122, 3053-3062.
35. Chen, H.; Kwait, D.C.; Gönen, Z.S.; Weslowski, B.T.; Abdallah, D.J.; Weiss, R.G. Phase characterization and properties of completely saturated quaternary phosphonium salts. Ordered, room-temperature ionic liquids. Chem. Mater. 2002, 14, 4063-4072.
36. Xu, W.; Cooper, E.I.; Angell, C.A. Ionic liquids: Ion mobilities, glass temperatures, and fragilities. J. Phys. Chem. B 2003, 107, 6170-6178.
37. Fraser, K.J.; Izgorodina, E.I.; Forsyth, M.; Scott, J.L.; MacFarlane, D.R. Liquids intermediate between ?molecular{norm of matrix} and ?ionic{norm of matrix} liquids: Liquid ion pairs? Chem Commun. 2007, 37 (Oct. 7), 3817-3819.
38. Ma, K.; Somashekhar, B.S.; Nagana Gowda, G.A.; Khetrapal, C.L.; Weiss, R.G. Induced amphotropic and thermotropic ionic liquid crystallinity in phosphonium halides: ?Lubrication{norm of matrix} by hydroxyl groups. Langmuir 2008, 24, 2746-2758.
39. Ma, K.; Lee, K.-M.; Minkova, L.; Weiss, R.G. Design criteria for ionic liquid crystalline phases of phosphonium salts with three equivalent long n-alkyl chains. J. Org. Chem. 2009, 74, 2088-2098.
40. Nieuwenhuyzen, M.; Seddon, K.R.; Teixidor, F.; Puga, A.V.; Viñas, C. Ionic liquids containing boron cluster anions. Inorg. Chem. 2009, 48, 889-901.
41. Plechkova, N.V.; Seddon, K.R. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev. 2008, 37, 123-150.
42. Dröge, T.; Glorius, F. NHC-Ligand der Ideen. Nachr. Chem. 2010, 58, 112-117.
43. Xiao, J.-C.; Twamley, B.; Shreeve, J.M. An ionic liquid-coordinated palladium complex: A highly efficient and recyclable catalyst for the Heck reaction. Org. Lett. 2004, 6, 3845-3847.
44. Deshmukh, R.R.; Rajagopal, R.; Srinivasan, K.V. Ultrasound promoted C-C bond formation: Heck reaction at ambient conditions in room temperature ionic liquids. Chem. Commun. 2001, 17, 1544-1545.
45. Bowlas, C.J.; Bruce, D.W.; Seddon K.R. Liquid-crystalline ionic liquids. Chem. Commun. 1996, 14, 1625-1626.
46. Downard, A.; Earle, M.J.; Hardacre, C.; McMath, S.E.J.; Nieuwenhuyzen, M.; Teat, S.J. Structural studies of crystalline 1-alkyl-3-methylimidazolium chloride salts. Chem. Mater. 2004, 16, 43-48.
47. Holbrey, J.D.; Seddon, K.R. The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; Ionic liquids and ionic liquid crystals. J. Chem. Soc., Dalton Trans. 1999, 13, 2133-2139.
48. Del Pópolo, M.G.; Kohanoff, J.; Lynden-Bell, R.M.; Pinilla, C. Clusters, liquids, and crystals of dialkylimidazolium salts. A combined perspective from ab initio and classical computer simulations. Acc. Chem. Res. 2007, 40, 1156-1164.
49. Hardacre, C.; Holbrey, J.D.; Mullan, C.L.; Youngs, T.G.A.; Bowron, D.T. Small angle neutron scattering from 1-alkyl-3-methylimidazolium hexafluorophosphate ionic liquids ([Cnmim][PF6], n = 4, 6, and 8). J. Chem. Phys. 2010, 133, 074510:1-074510:7.
50. Paulechka, Y.U.; Kabo, G.J.; Blokhin, A.V.; Shaplov, A.S.; Lozinskaya, E.I.; Golovanov, D.G.; Lyssenko, K.A.; Korlyukov, A.A.; Vygodskii, Ya.S. IR and X-ray study of polymorphism in 1-alkyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imides. J. Phys. Chem. B 2009, 113, 9538-9546.
51. Kaper, H.; Smarsly, B. Templating and phase behaviour of the long chain ionic liquid C16mimCl. Z. Phys. Chem. 2006, 220, 1455-1471.
52. Getsis, A.; Mudring, A.V. Imidazolium based ionic liquid crystals: Structure, photophysical and thermal behaviour of [Cnmim]Br·xH2O (n = 12, 14; x = 0, 1). Cryst. Res. Technol. 2008, 43, 1187-1196.
53. Getsis, A.; Tang, S.; Mudring, A.V. A luminescent ionic liquid crystal: [C12mim]4[EuBr6]Br. Eur. J. Inorg. Chem. 2010, 14, 2172-2177.
54. Godinho, M.H.; Cruz, C.; Teixeira, P.I.C.; Ferreira, A.J.; Costa, C.; Kulkarni, P.S.; Afonso, C.A.M. Shear-induced lamellar phase of an ionic liquid crystal at room temperature. Liq. Cryst. 2008, 35, 103-107.
55. Mehdi, H.; Binnemans, K.; Van Hecke, K.; Van Meervelt, L.; Nockemann, P. Hydrophobic ionic liquids with strongly coordinating anions. Chem. Commun. 2010, 46, 234-236.
56. Xu, F.; Matsumoto, K.; Hagiwara, R. Effects of alkyl chain length on properties of 1-alkyl-3-methylimidazolium fluorohydrogenate ionic liquid crystals. Chem. Eur. J. 2010, 16, 12970-12976.
57. Wang, X.; Heinemann, F.W.; Yang, M.; Melcher, B.U.; Fekete, M.; Mudring, A.-V.; 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, 47, 7405-7407.
58. Chiou, J.Y.Z.; Chen, J.N.; Lei, J.S.; Lin, I.J.B. Ionic liquid crystals of imidazolium salts with a pendant hydroxyl group. J. Mater. Chem. 2006, 16, 2972-2977.
59. 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, 528-532.
60. Dobbs, W.; Douce, L.; Heinrich, B. 1-(4-Alkyloxybenzyl)-3-methyl-1H-imidazol-3-ium organic backbone: A versatile smectogenic moiety. Beilstein J. Org. Chem. 2009, 5, DOI: 10.3762/bjoc.5.62.
61. Fouchet, J.; Douce, L.; Heinrich, B.; Welter, R.; Louati, A. A convenient method for preparing rigid-core ionic liquid crystals. Beilstein J. Org. Chem. 2009, 5, DOI: 10.3762/bjoc.5.51.
62. Suisse, J.M.; Bellemin-Laponnaz, S.; Douce, L.; Maisse-François, A.; Welter, R. A new liquid crystal compound based on an ionic imidazolium salt. Tetrahedron Lett. 2005, 46, 4303-4305.
63. Suisse, J.M.; Douce, L.; Bellemin-Laponnaz, S.; Maisse-François, A.; Welter, R.; Miyake, Y.; Shimizu, Y. Liquid crystal imidazolium salts: Towards materials for catalysis and molecular electronics. Eur. J. Inorg. Chem. 2007, 24, 3899-3905.
64. Li, X.; Bruce, D.W.; Shreeve, J.M. Dicationic imidazolium-based ionic liquids and ionic liquid crystals with variously positioned fluoro substituents. J. Mater. Chem. 2009, 19, 8232-8238.
65. Kouwer, P.H.J.; Swager, T.M. Synthesis and mesomorphic properties of rigid-core ionic liquid crystals. J. Am. Chem. Soc. 2007, 129, 14042-14052.
66. Goossens, K.; Nockemann, P.; Driesen, K.; Goderis, B.; Görller-Walrand, C.; van Hecke, K.; Van Meervelt, L.; Pouzet, E.; Binnemans, K.; Cardinaels, T. Imidazolium ionic liquid crystals with pendant mesogenic groups. Chem. Mater. 2008, 20, 157-168.
67. Zhang, Q.; Jiao, L.; Shan, C.; Hou, P.; Chen, B.; Xu, X.; Niu, L. Synthesis and characterisation of novel imidazolium-based ionic liquid crystals with a p-nitroazobenzene moiety. Liq. Cryst. 2008, 35, 765-772.
68. Zhang, Q.; Shan, C.; Wang, X.; Chen, L.; Niu, L.; Chen, B. New ionic liquid crystals based on azobenzene moiety with two symmetric imidazolium ion group substituents. Liq. Cryst. 2008, 35, 1299-1305.
69. Lévesque, I.; Leclerc, M. Novel dual photochromism in polythiophene derivatives. Macromolecules 1997, 30, 4347-4352.
70. Trilla, M.; Pleixats, R.; Parella, T.; Blanc, C.; Dieudonné, P.; Guari, Y.; Man, M.W.C. Ionic liquid crystals based on mesitylene-containing bis- and trisimidazolium salts. Langmuir 2008, 24, 259-265.
71. Yoshio, M.; Ichikawa, T.; Shimura, H.; Kagata, T.; Hamasaki, A.; Mukai, T.; Ohno, H.; Kato, T. Columnar liquid-crystalline imidazolium salts. Effects of anions and cations on mesomorphic properties and ionic conductivities. Bull. Chem. Soc. Jpn. 2007, 80, 1836-1841.
72. Yoshio, M.; Kagata, T.; Hoshino, K.; Mukai, T.; Ohno, H.; Kato, T. One-dimentional ion-conductive polymer films: Alignment and fixation of ionic channels formed by self-organization of polymerizable columnar liquid crystals. J. Am. Chem. Soc. 2006, 128, 5570-5577.
73. Pal, S.K.; Kumar, S. Microwave-assisted synthesis of novel imidazolium-based ionic liquid crystalline dimers. Tetrahedron Lett. 2006, 47, 8993-8997.
74. Kumar, S.; Pal, S.K. Synthesis and characterization of novel imidazolium-based ionic discotic liquid crystals with a triphenylene moiety. Tetrahedron Lett. 2005, 46, 2607-2610.
75. Kumar, S.; Gupta, S.K. The first examples of discotic liquid crystalline gemini surfactants. Tetrahedron Lett. 2010, 51, 5459-5462.
76. Cui, L.; Zhu, L. Ionic interaction induced novel ordered columnar mesophases in asymmetric discotic triphenylene salts. Liq. Cryst. 2006, 33, 811-818.
77. Alam, Md.A.; Motoyanagi, J.; Yamamoto, Y.; Fukushima, T.; Kim, J.; Kato, K.; Takata, M.; Saeki, A.; Seki, S.; Tagawa, S.; Aida, T. ?Bicontinuous cubic{norm of matrix} liquid crystalline materials from discotic molecules: A special effect of paraffinic side chains with ionic liquid pendants. J. Am. Chem. Soc. 2009, 131, 17722-17723.
78. Mukai, T.; Nishikawa, K. Synthesis and crystal structures of two ionic liquids with halogen-bonding groups: 4,5-Dibromo- and 4,5-diiodo-1-butyl-3-methylimidazolium trifluoromethanesulfonates. Solid State Sci. 2010, 12, 783-788.
79. Hunter, C.A.; Sanders, J.K.M. The nature of interactions. J. Am. Chem. Soc. 1990, 112, 5525-5534.
80. Wiggins, K.M.; Kerr, R.L.; Chen, Z.; Bielawski, C.W. Design, synthesis, and study of benzobis- and bibenz(imidazolium)-based ionic liquid crystals. J. Mater. Chem. 2010, 20, 5709-5714.
81. Knight, G.A.; Shaw, B.D. Long-chain alkyl pyridines and their derivatives new examples of liquid crystals. J. Chem. Soc. 1938, 46, 682-683.
82. Sudhölter, E.J.R.; Engberts, J.B.F.N.; de Jeu, W.H. Thermotropic liquid-crystalline behavior of some single- and double-chained pyridinium amphiphiles. J. Phys. Chem. 1982, 86, 1908-1913.
83. Nusselder, J.J.H.; Engberts, J.B.F.N.; van Doren, H.A. Liquid-crystalline and thermochromic behaviour of 4-substituted 1-methylpyridinium iodide surfactants. Liq. Cryst. 1993, 13, 213-225.
84. Kohnen, G.; Tosoni, M.; Tussetschläger, S.; Baro, A.; Laschat, S. Counterion effects on the mesomorphic properties of chiral imidazolium and pyridinium ionic liquids. Eur. J. Org. Chem. 2009, 32, 5601-5609.
85. Ster, D.; Baumeister, U.; Lorenzo Chao, J.; Tschierske, C.; Israel, G. Synthesis and mesophase behaviour of ionic liquid crystals. J. Mater. Chem. 2007, 17, 3393-3400.
86. Lo Celso, F.; Pibiri, I.; Triolo, A.; Triolo, R.; Pace, A.; Buscemi, S.; Vivona, N. Study on the thermotropic properties of highly fluorinated 1,2,4-oxodiazolylpyridinium salts and their perspective applications as ionic liquid crystals. J. Mater. Chem. 2007, 17, 1201-1208.
87. Guittard, F.; Taffin de Givenchy, E.; Geribaldi, S.; Cambon, A. Highly fluorinated thermotropic liquid crystals: An update. J. Fluorine Chem. 1999, 100, 85-96.
88. Misaki, S.; Takamatsu, S.; Suefuji, M.; Mitote, T.; Matsumura, M. The synthesis of fluorine containing phenyl benzoates and their properties as liquid crystals. Mol. Cryst. Liq. Cryst. 1981, 66, 123-132.
89. Baudoux, J.; Judeinstein, P.; Cahard, D.; Plaquevent, J.C. Design and synthesis of novel ionic liquid/liquid crystals (IL2Cs) with axial chirality. Tetrahedron Lett. 2005, 46, 1137-1140.
90. Tanabe, K.; Yasuda, T.; Kato, T. Luminescent ionic liquid crystals based on tripodal pyridinium salts. Chem. Lett. 2008, 37, 1208-1209.
91. Yang, J.; Zhang, Q.; Zhu, L.; Zhang, S.; Li, J.; Zhang, X.; Deng, Y. Novel ionic liquid crystals based on N-caprolactam as cations. Chem. Mater. 2007, 19, 2544-2550.
92. Sauer, S.; Steinke, N.; Baro, A.; Laschat, S.; Giesselmann, F.; Kantlehner, W. Guanidinium chlorides with triphenylene moieties displaying columnar mesophase. Chem. Mater. 2008, 20, 1909-1915.
93. Sauer, S.; Saliba, S.; Tussetschläger, S.; Baro, A.; Frey, W.; Giesselmann, F.; Laschat, S.; Kantlehner, W. p-Alkoxybiphenyls with guanidinium head groups displaying smectic mesophases. Liq. Cryst. 2009, 36, 275-299.
94. Butschies, M.; Sauer, S.; Kessler, E.; Siehl, H.-U.; Claasen, B.; Fischer, P.; Frey, W.; Laschat, S. Influence of N-alkyl substituents and counterions on the structural and mesomorphic properties of guanidinium salts: Experiment and quantum chemical calculations. Chem. Phys. Chem. 2010, 11, 3752-3765.
95. Yelamaggad, C.V.; Mathews, M.; Hiremath, U.S.; Shankar Rao, D.S.; Krishna Prasad, S. Self-assembly of chiral mesoionic heterocycles into smectic phases: A new class of polar liquid crystal. Tetrahedron Lett. 2005, 46, 2623-2626.
96. Causin, V.; Saielli, G. Effect of asymmetric substitution on the mesomorphic behaviour of low-melting viologen salts of bis(trifluoromethane)sulfonylamide. J. Mater. Chem. 2009, 19, 9153-9162.
97. Tanabe, K.; Yasuda, T.; Yoshio, M.; Kato, T. Viologen-based redox-active ionic liquid crystals forming columnar phases. Org. Lett. 2007, 9, 4271-4274.
98. Metallomesogens: Synthesis, Properties, and Applications, 1st ed.; Serrano, J.L., Ed.; VCH: Weinheim, Germany, 1996.
99. Galyametdinov, Y.G.; Haase, W.; Goderis, B.; Moors, D.; Driesen, K.; van Deun, R.; Binnemans, K. Magnetic alignment study of rare-earth-containing liquid crystals. J. Phys. Chem. B 2007, 111, 13881-13885.
100. Chang, H.C.; Shiozaki, T.; Kamata, A.; Kishida, K.; Ohmori, T.; Kiriya, D.; Yamauchi, T.; Furukawa, H.; Kitagawa, S. A redox-active columnar metallomesogen and its cyclic voltammetric responses. J. Mater. Chem. 2007, 17, 4136-4138.
101. Cavero, E.; Uriel, S.; Romero, P.; Serrano, J.L.; Giménez, R. Tetrahedral zinc complexes with liquid crystalline and luminescent properties: Interplay between nonconventional molecular shapes and supramolecular mesomorphic order. J. Am. Chem. Soc. 2007, 129, 11608-11618.
102. Wróbel, D.; Goc, J.; Ion, R.M. Photovoltaic and spectral properties of tetraphenyloporphyrin and metallotetraphenyloporphyrino dyes. J. Mol. Struct. 1998, 450, 239-246.
103. Vorländer, D. Verhalten der Salze organischer Säuren beim Schmelzen. Ber. Dtsch. Chem. Ges. 1910, 43, 3120-3135.
104. Garbovskiy, Y.; Koval'chuk, A.; Grydyakina, A.; Bugaychuk, S.; Mirnaya, T.; Klimusheva, G. Electrical conductivity of lyotropic and thermotropic ionic liquid crystals consisting of metal alkanoates. Liq. Cryst. 2007, 34, 599-603.
105. Casado Martínez, F.J.; Riesco Ramos, M.; Da Silva, I.; Labrador, A.; Redondo, M.I.; García Peréz, M.V.; López-Andrés, S.; Rodríguez Cheda, J.A. Thermal and structural study of the crystal phases and mesophases in the lithium and thallium(I) propanoates and pentanoates binary systems: Formation of mixed salts and stabilization of the ionic liquid crystal phase. J. Phys. Chem. B 2010, 114, 10075-10085.
106. Li, H.; Bu, W.; Qi, W.; Wu, L. Self-assembled multibilayers of europium alkanoates: Structure, photophysics, and mesomorphic behavior. J. Phys. Chem. B 2005, 109, 21669-21676.
107. Meng, F.B.; Cheng, C.S.; Zhang, B.Y.; He, X.Z. Synthesis and characterization of a novel liquid crystal-bearing ionic mesogen. Liq. Cryst. 2005, 32, 191-195.
108. Taubert, A.; Steiner, P.; Mantion, A. Ionic liquid crystal precursors for inorganic particles: Phase diagram and thermal properties of a CuCl nanoplatelet precursor. J. Phys. Chem. B 2005, 109, 15542-15547.
109. Dobbs, W.; Suisse, J.-M.; Douce, L.; Welter, R. Electrodeposition of silver particles and gold nanoparticles from ionic-liquid crystal precursors. Angew. Chem. 2006, 118, 4285-4288.
110. Getsis, A.; Balke, B.; Felser, C.; Mudring, A.V. Dysprosium-based ionic liquid crystals: Thermal, structural, photo- and magnetophysical properties. Cryst. Growth Des. 2009, 9, 4429-4437.
111. Mayoral, M.J.; Ovejero, P.; Campo, J.A.; Heras, J.V.; Pinilla, E.; Torres, M.R.; Cano, M. Ionic liquid crystals from ?-diketonyl containing pyridinium cations and tetrachlorozincate anions. Inorg. Chem. Commun. 2009, 12, 214-218.
112. Lin, I.J.B.; Vasam, C.S. Metal-containing ionic liquids and ionic liquid crystals based on imidazolium moiety. J. Organomet. Chem. 2005, 690, 3498-3512.
113. Piguet, C.; Bünzli, J.C.G.; Donnio, B.; Guillon, D. Thermotropic lanthanidomesogens. Chem. Commun. 2006, 36, 3755-3768.
114. Terazzi, E.; Guénée, L.; Morgantini, P.Y.; Bernardinelli, G.; Donnio, B.; Guillon, D.; Piguet, C. Tuning the polarization along linear polyaromatic strands for rationally inducing mesomorphism in lanthanide nitrate complexes. Chem. Eur. J. 2007, 13, 1674-1691.
115. Terazzi, E.; Suárez, S.; Torelli, S.; Nozary, H.; Imbert, D.; Mamula, O.; Rivera, J.P.; Guillet, E.; Bénech, J.M.; Bernardinelli, G.; Scopelliti, R.; Donnio, B.; Guillon, D.; Bünzli, J.C.G.; Piguet, C. Introducing bulky functional lanthanide cores into thermotropic metallomesogens: A bottom-up approach. Adv. Funct. Mater. 2006, 16, 157-168.
116. Jensen, T.B.; Terazzi, E.; Buchwalder, K.L.; Guénée, L.; Nozary, H.; Schenk, K.; Heinrich, B.; Donnio, B.; Guillon, D.; Piguet, C. Dimerization of dendrimeric lanthanide complexes: Thermodynamic, thermal, and liquid-crystalline properties. Inorg. Chem. 2010, 49, 8601-8619.
117. Suárez, S.; Mamula, O.; Scopelliti, R.; Donnio, B.; Guillon, D.; Terazzi, E.; Piguet, C.; Bünzli, J.C.G. Lanthanide luminescent mesomorphic complexes with macrocycles derived from diaza-18-crown-6. New J. Chem. 2005, 29, 1323-1334.
118. Percec, V.; Johansson, G.; Rodenhouse, R. Molecular recognition directed phase transitions in side-chain liquid crystalline polymers containing crown ethers. Macromolecules 1992, 25, 2563-2565.
119. Coco, S.; Cordovilla, C.; Espinet, P.; Gallani, J.-L.; Guillon, D.; Donnio, B. Supramolecular aggregates in fluid phases: Mesomorphic ortho-palladated complexes with substituted crown ethers and their potassium adducts. Eur. J. Inorg. Chem. 2008, 2008, 1210-1218.
120. Steinke, N.; Frey, W.; Baro, A.; Laschat, S.; Drees, C.; Nimtz, M.; Hägele, C.; Giesselmann, F. Columnar and smectic liquid crystals based on crown ethers. Chem. Eur. J. 2006, 12, 1026-1035.
121. Steinke, N.; Jahr, M.; Lehmann, M.; Baro, A.; Frey, W.; Tussetschläger, S.; Sauer, S.; Laschat, S. Crown ethers with lateral ortho-terphenyl units: Effect of ester groups and sodium salts on the mesomorphic properties. J. Mater. Chem. 2009, 19, 645-654.
122. Kaller, M.; Tussetschläger, S.; Fischer, P.; Deck, C.; Baro, A.; Giesselmann, F.; Laschat, S. Columnar mesophases controlled by counterions in potassium complexes of dibenzo[18]crown-6 derivatives. Chem. Eur. J. 2009, 15, 9530-9542.
123. Kaller, M.; Deck, C.; Meister, A.; Hause, G.; Baro, A.; Laschat, S. Counterion effects on the columnar mesophases of triphenylene-substituted [18]crown-6 ethers: Is flatter better? Chem. Eur. J. 2010, 16, 6326-6337.
124. Steinke, N.; Kaller, M.; Nimtz, M.; Baro, A.; Laschat, S. Columnar liquid crystals derived from crown ethers with two lateral ester-substituted ortho-terphenyl units: Unexpected destabilisation of the mesophase with potassium iodide. Liq. Cryst. 2010, 37, 1139-1149.
125. Kaharu, T.; Ishii, R.; Takahashi, S. Liquid-crystalline gold-isonitrile complexes. J. Chem. Soc. Chem. Commun. 1994, 1349-1350.
126. Lee, Y.A.; McGarrach, J.E.; Lachicotte, R.J.; Eisenberg, R. Multiple emissions and brilliant white luminescence from gold(I) o,o'-di(alkyl)dithiophosphate dimers. J. Am. Chem. Soc. 2002, 124, 10662-10663.
127. Bayón, R.; Coco, S.; Espinet, P. Gold liquid crystals displaying luminescence in the mesophase and short F···F interactions in the solid state. Chem. Eur. J. 2005, 11, 1079-1085.
128. Pucci, D.; Barberio, G.; Bellusci, A.; Crispini, A.; Donnio, B.; Giorgini, L.; Ghedini, M.; La Deda, M.; Szerb, E.I. Silver coordination complexes as room-temperature multifunctional materials. Chem. Eur. J. 2006, 12, 6738-6747.
129. Bellusci, A.; Ghedini, M.; Giorgini, L.; Gozzo, F.; Szerb, E.I.; Crispini, A.; Pucci, D. Anion dependent mesomorphism in coordination networks based on 2,2'-bipiridine silver(I) complexes. Dalton Trans. 2009, 36, 7381-7389.
130. Torralba, M.C.; Campo, J.A.; Heras, J.V.; Bruce, D.W.; Cano, M. Mesomorphism of ionic allylpalladium(II) complexes containing pzR2py as ligands and [BF4]-, [PF6]- or [CF3SO3]- as counteranions. Dalton Trans. 2006, 32, 3918-3926.
131. Torralba, M.C.; Cano, M.; Campo, J.A.; Heras, J.V.; Pinilla, E.; Torres, M.R. Liquid crystal behaviour of ionic allylpalladium complexes containing 2-pyrazolylpyridine as bidentate N,N'-ligand. J. Organomet. Chem. 2006, 691, 765-778.
132. Cardinaels, T.; Ramaekers, J.; Guillon, D.; Donnio, B.; Binnemans, K. A propeller-like uranyl metallomesogen. J. Am. Chem. Soc. 2005, 127, 17602-17603.
133. Cardinaels, T.; Ramaekers, J.; Nockemann, P.; Driesen, K.; Van Hecke, K.; Van Meervelt, L.; Lei, S.; De Feyter, S.; Guillon, D.; Donnio, B.; Binnemans, K. Imidazo[4,5-f]-1,10-phenanthrolines: Versatile ligands for the design of metallomesogens. Chem. Mater. 2008, 20, 1278-1291.
134. Cardinaels, T.; Ramaekers, J.; Driesen, K.; Nockemann, P.; Van Hecke, K.; Van Meervelt, L.; Goderis, B.; Binnemans, K. Thermotropic ruthenium(II)-containing metallomesogens based on substituted 1,10-phenanthroline ligands. Inorg. Chem. 2009, 48, 2490-2499.
135. Faul, C.F.J.; Antonietti, M. Ionic self-assembly: Facile synthesis of supramolecular materials. Adv. Mater. 2003, 15, 673-683.
136. Camerel, F.; Faul, C.F.J. Combination of ionic self-assembly and hydrogen bonding as a tool for the synthesis of liquid-crystalline materials and organogelators from a simple building block. Chem. Commun. 2003, 1515, 1958-1959.
137. Kato, T. Self-assembly of phase-segregated liquid crystal structures. Science 2002, 295, 2414-2418.
138. Kato, T. Hydrogen-bonded liquid crystals: Molecular self-assembly for dynamically functional material. Struct. Bonding 2000, 96, 95-146.
139. Kato, T.; Mizoshita, N.; Kanie, K. Hydrogen-bonded liquid crystalline materials: Supramolecular polymeric assembly and the induction of dynamic function. Macromol. Rapid Commun. 2001, 22, 797-814.
140. Kato, T.; Mizoshita, N.; Kishimoto, K. Functional liquid-crystalline assemblies: Self-organized soft materials. Angew. Chem. Int. Ed. 2006, 45, 38-68.
141. Yazaki, S.; Kamikawa, Y.; Yoshio, M.; Hamasaki, A.; Mukai, T.; Ohno, H.; Kato, T. Ionic liquid crystals: Self-assembly of imidazolium salts containing an l-glutamic acid moiety. Chem. Lett. 2008, 37, 538-539.
142. Noguchi, T.; Kishikawa, K.; Kohmoto, S. Volume effect of alkyl chains on organization of ionic self-assemblies toward hexagonal columnar mesophases. Bull. Chem. Soc. Jpn. 2008, 81, 778-783.
143. Noguchi, T.; Kishikawa, K.; Kohmoto, S. Tailoring liquid-crystalline supramolecular structures by ionic interactions. Chem. Lett. 2008, 37, 12-13.
144. Noguchi, T.; Kishikawa, K.; Kohmoto, S. Tailoring of ionic supramolecular assemblies based on ammonium carboxylates toward liquid-crystalline micellar cubic mesophases. Liq. Cryst. 2008, 35, 1043-1050.
145. Zakrevskyy, Y.; Smarsly, B.; Stumpe, J.; Faul, C.F.J. Highly ordered monodomain ionic self-assembled liquid-crystalline materials. Phys. Rev. E. 2005, 71, 021701:1-021701:12.
146. Olivier, J.H.; Camerel, F.; Barberá, J.; Retailleau, P.; Ziessel, R. Ionic liquid crystals formed by self-assembly around an anionic anthracene core. Chem. Eur. J. 2009, 15, 8163-8174.
147. Olivier, J.-H.; Camerel, F.; Ulrich, G.; Barberá, J.; Ziessel, R. Luminescent ionic liquid crystals from self-assembled bodipy disulfonate and imidazolium frameworks. Chem. Eur. J. 2010, 16, 7134-7142.
148. Camerel, F.; Ulrich, G.; Barberá, J.; Ziessel, R. Ionic self-assembly of ammonium-based amphiphiles and negatively charged bodipy and porphyrin luminophores. Chem. Eur. J. 2007, 13, 2189-2200.
149. Ringstrand, B.; Monobe, H.; Kaszynski, P. Anion-driven mesogenicity: Ionic liquid crystals based on [closo-1-CB9H10]- cluster. J. Mater. Chem. 2009, 19, 4805-4812.
150. Kohmoto, S.; Hara, Y.; Kishikawa, K. Hydrogen-bonded ionic liquid crystals: Pyridinylmethylimidazolium as a versatile building block. Tetrahedron Lett. 2010, 51, 1508-1511.
151. Macknight, W.J.; Ponomarenko, E.A.; Tirrell, D.A. Self-assembled polyelectrolyte-surfactant complexes in nonaqueous solvents and in the solid state. Acc. Chem. Res. 1998, 31, 781-788.
152. Zhou, S.; Chu, B. Assembled materials: Polyelectrolyte-surfactant complexes. Adv. Mater. 2000, 12, 545-556.
153. Batra, D.; Seifert, S.; Firestone, M.A. The effect of cation structure on the mesophase architecture of self-assembled and polymerized imidazolium-based ionic liquids. Macromol. Chem. Phys. 2007, 208, 1416-1427.
154. Lee, S.; Becht, G.A.; Lee, B.; Burns, C.T.; Firestone, M.A. Electropolymerization of a bifunctional ionic liquid monomer yields an electroactive liquid-crystalline polymer. Adv. Funct. Mater. 2010, 20, 2063-2070.
155. Jazkewitsch, O.; Ritter, H. Polymerizable ionic liquid crystals. Macromol. Rapid Commun. 2009, 30, 1554-1558.
156. Zhang, B.Y.; Meng, F.B.; Tian, M.; Xiao, W.Q. Side-chain liquid-crystalline polysiloxanes containing ionic mesogens and cholesterol ester groups. React. Funct. Polym. 2006, 66, 551-558.
157. Meng, F.B.; Zhang, B.Y.; Jia, Y.G.; Yao, D.S. Effect of ionic aggregates of sulphonate groups on the liquid crystalline behaviours of liquid crystalline elastomers. Liq. Cryst. 2005, 32, 183-189.
158. Xiao, S.; Lu, X.; Lu, Q. Photosensitive polymer from ionic self-assembly of azobenzene dye and poly(ionic liquid) and its alignment characteristic toward liquid crystal molecules. Macromolecules 2007, 40, 7944-7950.
159. Xiao, S.; Lu, X.; Lu, Q.; Su, B. Photosensitive liquid-crystalline supramolecules self-assembled from ionic liquid crystal and polyelectrolyte for laser-induced optical anisotropy. Macromolecules 2008, 41, 3884-3892.
160. Ujiie, S.; Furukawa, H.; Yano, Y.; Mori, A. Oriented glass states formed by ionic liquid-liquid crystals. Thin Solid Films 2006, 509, 185-188.
161. Ponomarenko, S.A.; Boiko, N.I.; Shibaev, V.P. Liquid-crystalline dendrimers. Vysokomol. Soedin. Ser. A B 2001, 43, 1601-1650.
162. Martín-Rapún, R.; Marcos, M.; Omenat, A.; Barberá, J.; Romero, P.; Serrano, J.L. Ionic thermotropic liquid crystal dendrimers. J. Am. Chem. Soc. 2005, 127, 7397-7403.
163. Marcos, M.; Martín-Rapún, R.; Omenat, A.; Barberá, J.; Serrano, J.L. Ionic liquid crystal dendrimers with mono-, di- and trisubstituted benzoic acids. Chem. Mater. 2006, 18, 1206-1212.
164. Antharjanam, P.K.S.; Jaseer, M.; Ragi, K.N.; Prasad, E. Intrinsic luminescence properties of ionic liquid crystals based on PAMAM and PPI dendrimers. J. Photochem. Photobiol. A Chem. 2009, 203, 50-55.
165. Cook, A.G.; Baumeister, U.; Tschierske, C. Supramolecular dendrimers: Unusual mesophases of ionic liquid crystals derived from protonation of DAB dendrimers with facial amphiphilic carboxylic acids. J. Mater. Chem. 2005, 15, 1708-1721.
166. Chen, Y.; Shen, Z.; Gehringer, L.; Frey, H.; Stiriba, S.E. Supramolecular thermotropic liquid crystalline materials with nematic mesophase based on methylated hyperbranched polyethylenimine and mesogenic carboxylic acid. Macromol. Rapid Commun. 2006, 27, 69-75.
167. Marcos, M.; Alcalá, R.; Barberá, J.; Romero, P.; Sánchez, C.; Serrano, J.L. Photosensitive ionic nematic liquid crystalline complexes based on dendrimers and hyperbranched polymers and a cyanoazobenzene carboxylic acid. Chem. Mater. 2008, 20, 5209-5217.
168. Taubert, A. CuCl nanoplatelets from an ionic liquid-crystal precursor. Angew. Chem. 2004, 116, 5494-5496.
169. Taubert, A.; Li, Z. Inorganic materials from ionic liquids. Dalton Trans. 2007, 7, 723-727.
170. Taubert, A.; Palivan, C.; Casse, O.; Gozzo, F.; Schmitt, B. Ionic liquid-crystal precursors (ILCPs) for CuCl nanoplatelets: The origin of the exothermic peak in DSC curves. J. Phys. Chem. C 2007, 111, 4077-4082.
171. Taubert, A.; Arbell, I.; Mecke, A.; Graf, P. Photoreduction of a crystalline Au(III) complex: A solid-state approach to metallic nanostructures. Gold Bull. 2006, 39, 205-211.
172. Wang, Q.T.; Wang, X.B.; Lou, W.J.; Hao, J.C. Stable blue- and green-emitting zinc oxide from ionic liquid crystal precursors. ChemPhysChem 2009, 10, 3201-3203.
173. 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, 351-354.
174. Shimura, H.; Yoshio, M.; Hoshino, K.; Mukai, T.; Ohno, H.; Kato, T. Noncovalent approach to one-dimensional ion conductors: Enhancement of ionic conductivities in nanostructured columnar liquid crystals. J. Am. Chem. Soc. 2008, 130, 1759-1765.
175. Kato, T. From nanostructured liquid crystals to polymer-based electrolytes. Angew. Chem. 2010, 122, 8019-8021.
176. Yazaki, S.; Funahashi, M.; Kagimoto, J.; Ohno, H.; Kato, T. Nanostructured liquid crystals combining ionic and electronic functions. J. Am. Chem. Soc. 2010, 132, 7702-7708.
177. Safavi, A.; Tohidi, M. Design and characterization of liquid crystal-graphite composite electrodes. J. Phys. Chem. C 2010, 114, 6132-6140.
178. Binnemans, K.; Görller-Walrand, C. Lanthanide-containing liquid crystals and surfactants. Chem. Rev. 2002, 102, 2303-2345.
179. Eliseeva, S.V.; Bünzli, J.C.G. Lanthanide luminescence for functional materials and bio-sciences. Chem. Soc. Rev. 2010, 39, 189-227.
180. Bünzli, J.-C.G. Benefiting from the unique properties of lanthanide ions. Acc. Chem. Res. 2006, 39, 53-61.
181. Bian, Z.Q.; Huang, C.H. Highly Efficient OLEDs with Phosphorescent Materials, 1st ed.; Yersin, H., Ed.; Wiley-VCH: Weinheim, Germany, 2008; Chapter 12, pp. 391-420.
182. Puntus, L.N.; Schenk, K.J.; Bünzli, J.C.G. Intense near-infrared luminescence of a mesomorphic ionic liquid doped with lanthanide β-diketonate ternary complexes. Eur. J. Inorg. Chem. 2005, 23, 4739-4744.
183. Binnemans, K. Luminescence of metallomesogens in liquid crystal state. J. Mater. Chem. 2009, 19, 448-453.
184. Highly Efficient OLEDs with Phosphorescent Materials, 1st ed.; Yersin, H., Ed.; Wiley-VCH: Weinheim, Germany, 2008; pp.1-390.
185. Evans, R.C.; Douglas, P.; Winscom, C.J. Coordination complexes exhibiting room-temperature phosphorescence: Evaluation of their suitability as triplet emitters in organic light emitting diodes. Coord. Chem. Rev. 2006, 250, 2093-2126.
186. Yersin, H.; Winkenzeller, W.J. Highly Efficient OLEDs with Phosphorescent Materials, 1st ed.; Yersin, H., Ed.; Wiley-VCH: Weinheim, Germany, 2008; Chapter 1, pp. 1-97.
187. Yersin, H.; Donges, D. Low-lying electronic states and photophysical properties of organometallic Pd(II) and Pt(II) compounds. modern research trends presented in detailed case studies. Top. Curr. Chem. 2001, 214, 81-186.
188. Szerb, E.I.; Talarico, A.M.; Aiello, I.; Crispini, A.; Godbert, N.; Pucci, D.; Pugliese, T.; Ghedini, M. Green to red switch driven by order in an ionic IrIII liquid-crystalline complex. Eur. J. Inorg. Chem. 2010, 2010, 3270-3277.
189. O;Regan, B.; Grätzel, M. A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. Nature 1991, 353, 737-740.
190. Hagfeldt, A.; Boschloo, G.; Sun, L.; Kloo, L.; Pettersson, H. Dye-sensitized solar cells. Chem. Rev. 2010, 110, 6595-6663.
191. Zakeeruddin, S.M.; Grätzel, M. Solvent-free ionic liquid electrolytes for mesoscopic dye-sensitized solar cells. Adv. Funct. Mater. 2009, 19, 2187-2202.
192. Gorlov, M.; Kloo, L. Ionic liquid electrolytes for dye-sensitized solar cells. Dalton Trans. 2008, 2655-2666, DOI:10.1039/b716419j.
193. Yamanaka, N.; Kawano, R.; Kubo, W.; Kitamura, T.; Wada, Y.; Watanabe, M.; Yanagida, S. Ionic liquid crystal as a hole transport layer of dye-sensitized solar cells. Chem. Commun. 2005, 6, 740-742.
194. Kawano, R.; Nazeeruddin, Md.K.; Sato, A.; Grätzel, M.; Watanabe, M. Amphiphilic ruthenium dye as an ideal sensitizer in conversion of light to electricity using ionic liquid crystal electrolyte. Electrochem. Commun. 2007, 9, 1134-1138.
195. 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, 4763-4769.
196. Zhao, Y.; Zhai, J.; He, J.; Chen, X.; Chen, L.; Zhang, L.; Tian, Y.; Jiang, L.; Zhu, D. High-performance all-solid-state dye-sensitized solar cells utilizing imidazolium-type ionic crystal as charge transfer layer. Chem. Mater. 2008, 20, 6022-6028.
197. Dobbs, W.; Heinrich, B.; Bourgogne, C.; Donnio, B.; Terazzi, E.; Bonnet, M.E.; Stock, F.; Erbacher, P.; Bolcato-Bellemin, A.L.; Douce, L. Mesomorphic imidazolium salts: new vectors for efficient siRNA transfection. J. Am. Chem. Soc. 2009, 131, 13338-13346.
198. Desigaux, L.; Sainlos, M.; Lambert, O.; Chevre, R.; Letrou-Bonneval, E.; Vigneron, J.P.; Lehn, P.; Lehn, J.M.; Pitard, B. Self-assembled lamellar complexes of siRNA with lipidic aminoglycoside derivatives promote efficient siRNA delivery and interference. Proc. Natl. Akad. Sci.USA 2007, 104, 16534-16539.