Ferroelectric and antiferroelectric smectic and columnar liquid crystalline phases formed by silylated and non-silylated molecules with fluorinated bent cores

Chemistry of Materials

Volumn 19, Issue 4, 2007, Pages 694-710

  Keith, Christina ^a   Dantlgraber, Gert ^a   Reddy, R Amaranatha ^a,b   Baumeister, Ute ^a   Tschierske, Carsten ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC CORES; ELECTROOPTICAL INVESTIGATIONS; FERROELECTRIC SWITCHING; OBLIQUE LATTICE; OLIGOSILOXANE;

CHIRALITY; FERROELECTRIC MATERIALS; FLUORINE COMPOUNDS; PHASE STRUCTURE; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

SMECTIC LIQUID CRYSTALS;

EID: 33947155857     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm061749x     Document Type: Article

References (104)

1. Sayar, M.; Olvera de la Cruz, M.: Stupp, S. I. Europhys. Lett. 2003, 61, 334-340.
2. Lagerwall, S.T. In Handbook of liquid crystals; Demus, D., Goodby, J. W., Gray, G. W., Spiess, H.-W., Vill, V., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2B, pp 515-664.
3. Kitzerow, H.-S.; Bahr, C. Chirality in Liquid Crystals; Springer: New York, 2001.
4. Niori, T.; Sekine, T.; Watanabe, J.; Furukawa, T.; Takezoe, H. J. Mater. Chem. 1996, 6, 1231-1233.
5. Reviews: (a) Pelzl, G.; Diele, S.; Weissflog, W. Adv. Mater. 1999, 11, 707-724.
6. (b) Tschierske, C.; Dantlgraber, G. Pramana 2003, 61, 455-481.
7. (c) Ros, M. B.; Serrano, J. L.; de la Fuente, M. R.; Folcia, C. L. J. Mater. Chem. 2005, 15, 5093-5098.
8. (d) Reddy, R. A.; Tschierske, C. J. Mater. Chem. 2006, 16, 907-961.
9. (e) Takezoe, H.; Takanishi, Y. Jpn. J. Appl. Phys. 2006, 45, 597-625.
10. (a) Link, D. R.; Natale, G.; Shao, R.; Maclennan, J. E.; Clark, N. A.; Körblova, E.; Walba, D. M. Science 1997, 278, 1924-1927.
11. (b) Walba, D. M. Topics in Stereochemistry, Green, M. M., Nolte, R. J. M., Meijer, E. W., Eds.; Wiley: New York, 2003; Vol. 42 (Materials-Chirality), pp 475-518.
12. The subscript "F' is used for FE switching phases with a proven FE ground-state structure in the bulk (before application of an external field, see ref 81); for mesophases where a FE switching is found experimentally, but where the virgin ground-state structure is unknown or nonpolar the subscript FE is used, as suggested in ref 5d.
13. Examples of non-silylated FE switching bent-core materials: (a) Walba, D. M.; Körblova, E.; Shao, R.; Maclennan, J. E.; Link, D. R.; Glaser, M. A.; Clark, N. A. Science 2000, 288, 2181-2184.
14. (b) Nakata, M.; Link, D. R.; Araoka, F.; Thisayukta, J.; Takanishi, Y.; Ishikawa, K.; Watanabe, J.; Takezoe, H. Liq. Cryst. 2001, 28, 1301-1308.
15. (c) Bedel, J. P.; Rouillon, J. C.; Marcerou, J. P.; Laguerre, M.; Nguyen, H. T.; Achard, M. F. J. Mater. Chem. 2002, 12, 2214-2220.
16. (d) Reddy, R. A.; Sadashiva, B. K. J. Mater. Chem. 2002, 12, 2627-2642.
17. (e) Reddy, R. A.; Sadashiva, B. K. Liq. Cryst. 2003, 30, 1031 -1050.
18. (f) Rauch, S.; Bault, P.; Sawade, H.; Heppke, G.; Nair, G. G.; Jakli, A. Phys. Rev. E. 2002, 66, 021706.
19. (g) Kumazawa, K.; Nakata, M.; Araoka, F.; Takanishi, Y.; Ishikawa, K.; Watanabe, J.; Takezoe, H. J. Mater. Chem. 2004, 14, 157-164.
20. (h) Reddy, R. A.; Raghunathan, V. A.; Sadashiva, B. K. Chem. Mater. 2005, 17, 274-283.
21. (i) Nadasi, H.; Weissflog, W.; Eremin, A.; Pelzl, G.; Diele, S.; Das, S.; Grande, S. J. Mater. Chem. 2002, 12, 1316-1324.
22. (j) Bedel, J. P.; Rouillon, J. C.; Marcerou, J. P.; Nguyen, H. T.; Achard, M. F. Phys. Rev. E 2004, 69, 061702.
23. (k) Lee, S.K.; Heo, S.; Lee, J.-G.; Kang, K.-T.; Kumazawa, K.; Nishida, K.; Shimbo, Y.; Takanishi, Y.; Watanabe, J.; Doi, T.; Takahashi, T.; Takezoe H., J. Am. Chem. Soc. 2005, 127, 11085-11091.
24. (1) Nishida, K.; Cepic, M.; Kim, W. J.; Lee, S.K.; Heo, S.; Lee, J. G.; Takanishi, Y.; Ishikawa, K.; Kang, K.-T.; Watanabe, J.; Takezoe, H. Phys. Rev. E. 2006, 74, 021704.
25. Dark conglomerate phase of non-silylated molecules : (a) Thisayukta, J.; Nakayama, Y.; Kawauchi, S.; Takezoe, H.; Watanabe, J. J. Am. Chem. Soc. 2000, 122, 7441-7448.
26. (b) Thisayukta, J.; Kamee, H.; Kawauchi, S.; Watanabe, J. Mol. Cryst. Liq. Cryst. 2000, 346, 63-75.
27. (c) Shreenivasa Murthy, H. N.; Sadashiva, B. K. Liq. Cryst. 2002, 29, 1223-1234.
28. (d) Ortega, J.; Folcia, C. L.; Etxebarria, J.; Gimeno, N.; Ros, M. B. Phys. Rev. E 2003, 68, 011707.
29. (e) Weissflog, W.; Schröder, M. W.; Diele, S.; Pelzl, G. Adv. Mater. 2003, 15, 630-633.
30. (f) Jakli, A.; Huang, Y.-M.; Fodor-Csorba, K.; Vajda, A.; Galli, G.; Diele, S.; Pelzl, G. Adv. Mater. 2003, 15, 1606-1610.
31. (g) Schröder, M. W.; Diele, S.; Pelzl, G.; Dunemann, U.; Kresse, H.; Weissflog, W. J. Mater. Chem. 2003, 13, 1877-1882.
32. (h) Schröder, M. W.; Pelzl, G.; Dunemann, U.; Weissflog, W. Liq. Cryst. 2004, 31, 633-637.
33. (i) Weissflog, W.; Sokolowski, S.; Dehne, H.; Das, B.; Grande, S.; Schröder, M. W.; Eremin, A.; Diele, S.; Pelzl, G.; Kresse, H. Liq. Cryst. 2004, 31, 923-933.
34. [*] phases: (a) Heppke, G.; Parghi, D. D.; Sawade, H. Liq. Cryst. 2000, 27, 313-320.
35. (b) Etxebarria, J.; Folcia, C. L.; Ortega, J.; Ros, M. B. Phys. Rev. E 2003, 67, 042702.
36. Hough, L. E.; Clark, N. A. Phys. Rev. Lett. 2005, 95, 107802.
37. Keith, C.; Reddy, R. A.; Hauser, A.; Baumeister, U.; Tschierske, C. J. Am. Chem. Soc. 2006, 16, 3051-3066.
38. (a) Dantlgraber, G.; Eremin, A.; Diele, S.; Hauser, A.; Kresse, H.: Pelzl, G.; Tschierske, C. Angew. Chem., Int. Ed. 2002, 41, 2408-2412.
39. (b) Reddy, R. A.; Dantlgraber, G.; Baumeister, U.; Tschierske. C. Angew. Chem., Int. Ed. 2006, 45, 1928-1933.
40. Keith, C.; Reddy, R. A.; Hahn, H.; Lang, H.; Tschierske, C. Chem. Commun. 2004, 1898-1899.
41. (a) Keith, C.; Reddy, R. A.; Baumeister, U.; Tschierske, C. J. Am. Chem. Soc. 2004, 126, 14312-14313.
42. (b) Keith, C.; Reddy, R. A.: Prehm, M.; Baumeister, U.; Kresse, H.; Lorenzo Chao, J.; Hahn, H.; Lang., H.; Tschierske, C. Chem. Eur. J., DOI: 10.1002/chem.200600876.
43. (a) Dantlgraber, G.; Diele, S.; Tschierske, C. Chem. Commun. 2002, 2768-2769.
44. (b) Keith, C.; Reddy, R. A.; Baumeister, U.; Hahn, H.; Lang., H.; Tschierske, C. J. Mater. Chem., 2006, 16, 3444-3447.
45. Kosata, B.; Tamba, G.-M.; Baumeister, U.; Pelz, K.; Diele, S.; Pelzl, G.; Galli, G.; Samaritani, S.; Agina, E. V.; Boiko, N. I.; Shibaev, V. P.; Weissflog, W. Chem. Mater. 2006, 18, 691-701.
46. (a) Dantlgraber, G.; Baumeister, U.; Diele, S.; Kresse, H.; Lühmann, B.; Lang, H.; Tschierske, C. J. Am. Chem. Soc. 2002, 124, 14852-14853.
47. (b) Hahn, H.; Keith, C.; Lang., H.; Reddy, R. A.; Tschierske, C. Adv. Mater. 2006, 18, 2629-2633.
48. (a) Keith, C.; Reddy, R. A.; Tschierske, C. Chem. Commun. 2005, 871-873.
49. (b) Achten, A.; Koudijs, A.; Giesbers, M.; Reddy, R. A.; Verhulst, T.; Tschierske, C. Marcelis, A. T. M.; Sudhölter, E. J. R. Liq. Cryst. 2006, 33, 681-688.
50. (a) Shreenivasa Murthy, H. N.; Sadashiva, B. K. J. Mater. Chem. 2004, 14, 2813-2821.
51. (b) Achten, R.; Smits, E. A. W.; Reddy, R. A.; Giesbers, M.; Marcelis, A. T. M.; Sudhölter, E. J. R. Liq. Cryst. 2006, 33, 57-65.
52. (a) Bedel, J. P.; Rouillon, J. C.; Marcerou, J. P.; Laguerre, M.; Achard, M. F.; Nguyen, H. T. Liq. Cryst. 2000, 27, 103-113.
53. (b) Dierking, I.; Sawade, H.; Heppke, G. Liq. Cryst. 2001, 28, 1767-1773.
54. (c) Weissflog, W.; Nadasi, H.; Dunemann, U.; Pelzl, G.; Diele, S.; Eremin, A.; Kresse, H. J. Mater. Chem. 2001, 11, 2748-2758.
55. (d) Eremin, A.; Diele, S.; Pelzl, G.; Nadasi, H.; Weissflog, W. Phys. Rev. E 2003, 63, 021702.
56. (a) Shen, D.; Diele, S.; Wirth, I.; Tschierske, C. Chem. Commun. 1998, 2573-2574.
57. (b) Shen, D.; Pegenau, A.; Diele, S.; Wirth, I.; Tschierske, C. J. Am. Chem. Soc. 2000, 122, 1593-1601.
58. Dantlgraber, G.; Shen, D.; Diele, S.; Tschierske, C. Chem. Mater. 2002, 14, 1149-1158.
59. (a) Kelly, S. M. Helv. Chim. Acta 1989, 72, 594-607.
60. (b) Nabor, M. F.; Nguyen, H. T.; Destrade, C.; Marcerou, J. P.; Twieg, J. Liq. Cryst. 1991, 10, 785-797.
61. Achten, R.; Koudijs, A.; Giesbers, M.; Marcelis, A. T. M.; Sudhölter, E. J. R. Liq. Cryst. 2005, 32, 277-285.
62. A).
63. Examples of columnar phases formed by bent-core molecules: (a) Watanabe, J.; Niori, T.; Sekine, T.; Takezoe, H. Jpn. J. Appl. Phys. 1998, 37, L139-L142.
64. (b) Mieczkowski, J.; Gomola, K.; Koseska, J.; Pociecha, D.; Szydlowska, J.; Gorecka, E. J. Mater. Chem. 2003, 13, 2132-2137.
65. (c) Reddy, R. A.; Sadashiva, B. K.; Raghunathan, V. A. Chem. Mater. 2004, 16, 4050-4062.
66. (d) Pelz, K.; Weissflog, W.; Baumeister, U.; Diele, S. Liq. Cryst. 2003, 30, 1151-1158.
67. (e) Kardas, D.; Prehm, M.; Baumeister, U.; Pociecha, D.; Reddy, R. A.; Mehl, G. H.; Tschierske, C. J. Mater. Chem. 2005, 15, 1722-1733.
68. (f) See ref 21b. (h) Nguyen, H. T.; Bedel, J. P.; Rouillon, J. C.; Marcerou, J. P.; Achard, M. F. Pramana, J. Phys. 2003, 61, 395-404.
69. Gorecka, E.; Vaupotic, N.; Pociecha, D.; Cepic, M.; Mieczkowski, J. ChemPhysChem 2005, 6, 1087-1093.
70. (g) Takanishi, Y.; Takezoe, H.; Watanabe, J.; Takahashi, Y.; Lida, A. J. Mater. Chem. 2006, 16, 816-818.
71. mol corrected for the less dense packing in the liquid crystal assuming the packing coefficient to be intermediate between the average packing coefficient in the crystalline (k = 0.7) and liquid state (k = 0.55) (Kitaigorodski, A. I. "Molekülkristalle", Akademieverlag Berlin, 1979, see Table S2).
72. Achard, M. F.; Bedel, J. Ph.; Marcerou, J. P.; Nguyen, H. T.; Rouillon, J. C. Eur. Phys. J. E 2003, 10, 129-134.
73. Reddy R. A.; Sadashiva, B. K. J. Mater. Chem. 2004, 14, 1936-1947.
74. Examples of polar switching columnar phases of non-silylated compounds: (a) Reddy, R. A.; Sadashiva, B. K.; Baumeister, U. J. Mater. Chem. 2005, 15, 3303-3316.
75. (b) Umadevi, S.; Sadashiva, B. K.; Shreenivasa Murthy, H. N.; Raghunathan, V. A. Soft Matter 2006, 2, 210-214.
76. (c) Gorecka, E.; Pociecha, D.; Mieczkowski, J.; Matraszek, J.; Guillon, D.; Donnio, B. J. Am. Chem. Soc. 2004, 126, 15946-15947.
77. (d) Weissflog, W.; Naumann, G.; Kosata, B.; Schröder, M. W.; Eremin, A.; Diele, S.; Vakhovskaya, Z.; Kresse, H.; Friedemann, R.; Ananda Ramakrishnan, S.; Pelzl, G. J. Mater. Chem. 2005, 15, 4328-4337.
78. Coleman, D. A.; Fernsler, J.; Chattham, N.; Nakata, M.; Takanishi, Y.; Korblova, E.; Link, D. R.; Shao, R.-F.; Jang, W. G.; Maclennan, J. E.; Mondainn-Monval, O.; Boyer, C.; Weissflog, W.; Pelzl, G.; Chien, L.-C.; Zasadzinski, J.; Watanabe, J.; Walba, D. M.; Takezoe H.; Clark, N. A. Science 2003, 301, 1204-1211.
79. FE phases of 4a and 5a the splay seems to be relatively weak, as it can be removed under an electric field, leading to a FE switching smectic phase. Also, formation of an oblique lattice instead of a rectangular one is in line with a relatively weak splay of polarization.
80. (a) Pelzl, G.; Diele, S.; Jakli, A.; Lischka, C.; Wirth, I.; Weissflog, W. Liq. Cryst. 1999, 26, 135-139.
81. (b) Reddy, R. A.; Sadashiva, B. K. Liq. Cryst. 2003, 30, 273-283.
82. (b) Shreenivasa Murthy H. N.; Sadashiva, B. K. J. Mater. Chem. 2003, 13, 2863-2869.
83. (c) Shreenivasa Murthy, H. N.; Sadashiva, B. K. Liq. Cryst. 2003, 30, 1051-1055.
84. (d) Shreenivasa Murthy, H. N.; Sadashiva, B. K. J. Mater. Chem. 2003, 13, 2863-2869.
85. (e) Dunemann, U.; Schröder, M. W.; Reddy, R. A.; Pelzl, G.; Diele, S.; Weissflog, W. J. Mater. Chem. 2005, 15, 4051-4061.
86. (f) Pelzl, G.; Schröder, M. W; Dunemann, U.; Diele, S.; Weissflog, W.; Jones, C.; Coleman, D.; Clark, N.A.; Stannarius, R.; Li, J.; Dasc, B.; Grande, S. J. Mater. Chem. 2004, 14, 2492-2498.
87. 7-type phases: Nakata, M.; Link, D. R.; Takanishi, Y.; Takahasi, Y.; Thisayukta, J.; Niwano.H. Coleman, D.A.; Watanabe, J.; Iida, A.; Clark, N. A.; Takezoe, H. Phys. Rev. E 2005, 71, 011705.
88. Examples of field-induced Col to Sm transitions: (a) Ortega, J.; de la Fuente, M. R.; Etxebarria, J.; Folcia, C. L.; Diez, S.; Gallastegui, J. A.; Gimeno, N.; Ros, M. B. Phys. Rev. E 2004, 69, 011703.
89. (b) Etxebarria, J.; Folcia, C. L.; Ortega, J.; Ros, M. B. Phys. Rev. E 2003, 67, 042702.
90. FE switching on a cone is in principle possible in flat layers as well as in modulated and undulated layers. In contrast, in AF switching modulated (columnar) phases the switching on a cone is hindered for steric reasons (an unfavorable packing would arise at the inter-ribbon interfaces), and therefore, switching around the molecular long axis is observed instead of the switching on a cone.
91. FE switching by rotation on a cone was also observed for a FE switching columnar phase of bent-core dimesogens: Umadevi, S.; Jakli, A.; Sadashiva, B. K. Soft Matter 2006, 2, 215-222.
92. Examples for switching of suprastructural chirality by collective rotation around the long axis: (a) Schröder, M. W.; Diele, S.; Pelzl, G.; Weissflog, W. ChemPhysChem 2004, 5, 99-103.
93. (b) Szydlowska, J.; Mieczkowski, J.; Matraszek, J.; Bruce, D. W.; Gorecka, E.; Pociecha, D.; Guillon, D. Phys. Rev. E 2003, 67, 031702.
94. (c) Reddy, R. A.; Schröder, M. W.; Bodyagin, M.; Kresse, H.; Diele, S.; Pelzl, G.; Weissflog, W. Angew. Chem., Int. Ed. 2005, 44, 774-778.
95. (d) Weissflog, W.; Dunemann, U.; Schröder, M. W.; Diele, S.; Pelzl, G.; Kresse, H.; Grande, S. J. Mater. Chem. 2005, 15, 939-946.
96. (e) Nakata, M.; Shao, R. F.; Maclennan, J.; Weissflog, W.; Clark, N. A. Phys. Rev. Lett. 2006, 96, 067802.
97. 8d.20,21,30 whereas in calamitic mesogens lateral F substituents usually reduce the transition temperatures: Takeshi, I. In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R.E., et al., Eds.; Plenum Press: New York, 1994; pp 263-286.
98. Liao, G.; Stojadinovic, S.; Pelzl, G.; Weissflog, W.; Sprunt, S.; Jákli, A. Phys. Rev. E, 2005, 72, 021710.
99. aPA structure obtained at 0 V should be the same as that proposed for the dark conglomerate textures in the ground state of these mesophases with the difference that it is not optically isotropic.
100. (a) Folcia, C. L.; Ortega, J.; Etxebarria, J. Liq. Cryst. 2003, 30, 1189-1191.
101. (b) Pyc, P.; Mieczkowski, J.; Pociecha, D.; Gorecka, E.; Donnio, B.; Guillon, D. J. Mater. Chem. 2004, 14, 2374-2379.
102. A structure at 0 V.
103. The absence of an odd-even effect (see ref 12) is an additional indication of the week coupling between the layers.
104. Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.