Axial-bundle phases - New modes of 2D, 3D, and helical columnar self-assembly in liquid crystalline phases of bolaamphiphiles with swallow tail lateral chains

Journal of the American Chemical Society

Volumn 133, Issue 13, 2011, Pages 4906-4916

  Prehm, Marko ^a   Liu, Feng ^b   Zeng, Xiangbing ^b   Ungar, Goran ^b,c   Tschierske, Carsten ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

^c Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC CORES; BOLAAMPHIPHILES; COLUMNAR PHASE; COLUMNAR PHASIS; HEXAGONAL HONEYCOMB; HIGHER-DEGREE; HIGHEST TEMPERATURE; HYDROGEN BONDINGS; INTERCOLUMNAR CORRELATION; LATERAL CHAINS; LIQUID-CRYSTALLINE; LIQUID-CRYSTALLINE PHASIS; LONG AXIS; MATRIX; P-TERPHENYL; POLARIZING MICROSCOPY; ROD BUNDLES; VORONOI CELL; XRD;

AROMATIZATION; CRYSTALLINE MATERIALS; DIFFERENTIAL SCANNING CALORIMETRY; FLUORINE; GLYCEROL; HYDROGEN BONDS; LIQUIDS; ORGANIC POLYMERS; SELF ASSEMBLY; SYNTHESIS (CHEMICAL); THREE DIMENSIONAL; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

AROMATIC COMPOUNDS;

ALIPHATIC COMPOUND; CRYSTALLIN; FLUORINE; NANOROD;

ARTICLE; CHEMICAL STRUCTURE; FLUORINATION; PERIODICITY; TEMPERATURE; X RAY DIFFRACTION;

FURANS; LIQUID CRYSTALS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; PYRIDONES;

EID: 79953715443     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110065r     Document Type: Article

References (129)

1. Steed, J. W.; Atwood, J. L. Encyclopedia of Supramolecular Chemistry; Marcel Dekker: New York, 2004.
2. Stewart, G. T. Liq. Cryst. 2003, 30, 541-557
3. Stewart, G. T. Liq. Cryst. 2004, 31, 443-471
4. Lydon, J. Liq. Cryst. Today 2006, 15, 1-10
5. Lydon, J. Liq. Cryst. Today 2004, 13, 1-13
6. Nakata, M.; Zanchetta, G.; Chapman, B. D.; Jones, C. D.; J. O. Cross, J. O.; Pindak, R.; Bellini, T.; Clark, N. A. Science 2007, 318, 1276-1279
7. Collings, P. J.; Hird, M. Introduction to Liquid Crystals; Taylor & Francis: London, 1997.
8. Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H.-W.; Vill, V. Handbook of Liquid Crystals, Wiley-VCH: Weinheim, Germany, 1998; Vol. 1-3.
9. Pauluth, D.; Tarumi, K. J. Mater. Chem. 2004, 14, 1219-1227
10. Tschierske, C. Annu. Rep. Prog. Chem., Sect. C: Phys. Chem. 2001, 97, 191-267
11. Kato, T.; Mizoshita, N.; Kishimoto, K. Angew. Chem., Int. Ed. 2006, 45, 38-68
12. Ungar, G.; Zeng, X. Soft Matter 2005, 1, 95-106
13. Donnio, B.; Guillon, D. Adv. Polym. Sci. 2006, 201, 45-155
14. Saez, I. M.; Goodby, J. W. Struct. Bonding (Berlin) 2008, 128, 1-62
15. Chandrasekhar, S.; Sadashiva, B. K.; Suresh, K. A. Pramana 1977, 9, 471-480
16. Guillon, D. In Structure and Bonding, Liquid Crystals II; Mingos, D. M. P, Ed.; Springer: Berlin, Germany, 1999; Vol. 95, pp 41 - 82.
17. Bushby, R. J.; Lozman, O. R. Curr. Opin. Colloid Interface Sci. 2002, 7, 343-354
18. Laschat, S.; Baro, A.; Steinke, N.; Giesselmann, F.; Hägele, C.; Scalia, G.; Judele, R.; Kapatsina, E.; Sauer, S.; Schreivogel, A.; Tosoni, M. Angew. Chem., Int. Ed. 2007, 46, 4832-4887
19. Pisula, W.; Zorn, M.; Chang, J. Y.; Müllen, K.; Zentel, R. Macromol. Rapid Commun. 2009, 30, 1179-1202
20. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718-747
21. Sergeyev, S.; Pisula, W.; Geerts, Y. H. Chem. Soc. Rev. 2007, 36, 1902-1929
22. Pisula, W.; Feng, X.; Müllen, K. Adv. Mater. 2010, 22, 3634-3649
23. Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L. D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Würthner, F. Chem.-Eur. J. 2007, 13, 436-449
24. Chen, Z.; Baumeister, U.; Tschierske, C.; Würthner, F. Chem.-Eur. J. 2007, 13, 450-465
25. Malthete, J.; Levelut, A. M.; Tinh, N. H. J. Phys., Lett. 1985, 46, L875-880
26. Tinh, N. H.; Malthete, J.; Destrade, C. Mol. Cryst. Liq. Cryst. Lett. 1985, 2, 133-138
27. Tinh, N. H.; Destrade, C.; Levelut, A. M.; Malthete, J. J. Phys. (Paris) 1986, 47, 553-557
28. Guillon, D.; Skoulios, A.; Malthete, J. Europhys. Lett. 1987, 3, 67-72
29. Destrade, C.; Tinh, N. H.; Roubineau, A.; Levelut, A. M. Mol. Cryst. Liq. Cryst. 1988, 159, 163-171
30. Levelut, A. M.; Malthete, J.; Destrade, C.; Tinh, N. H. Liq. Cryst. 1987, 2, 877-888
31. Nguyen, N. T.; Destrade, C.; Malthete, J. Liq. Cryst. 1990, 8, 797-811
32. Reviews: Malthete, J.; Nguyen, H. T.; Destrade, C. Liq. Cryst. 1993, 13, 171-187
33. Nguyen, H. T.; Destrade, C.; Malthete, J. Adv. Mater. 1997, 9, 375-388
34. Nguyen, H. T.; Destrade, C.; Malthete, J. In Handbook of Liquid Crystals; Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H.-W.; Vill, V., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2B, pp 865 - 900.
35. Gharbia, M.; Gharbi, A.; Nguyen, H. T.; Malthete, J. Curr. Opin. Colloid Interface Sci. 2002, 7, 312-325
36. Bruce, D. W. Acc. Chem. Res. 2000, 33, 831-840
37. Originally the term "phasmidic" referred to rod-like molecules with three alkyl chains at both ends; "biforked" mesogens have two alkyl chains at both ends; now these molecules are generally named "polycatenar", where six-, five-, four-, and three-chain compounds are labeled hexa-, penta-, tetra-, and tricatenar, respectively; see ref 11c.
38. Donnio, B.; Heinrich, B.; Gulik-Krzywicki, T.; Delacroix, H.; Guillon, D.; Bruce, D. W. Chem. Mater. 1997, 9, 2951-2965
39. Bruce, D. W. Acc. Chem. Res. 2000, 33, 831-840
40. Achard, M. F.; Tinh, N. H.; Richard, H.; Mauzac, M.; Hardouin, F. Liq. Cryst. 1990, 84, 533-544
41. Percec, V.; Heck, J.; Ungar, G. Macromolecules 1991, 24, 4957-4962
42. Ungar, G.; Abramic, D.; Percec, V.; Heck, J. A. Liq. Cryst. 1996, 21, 73-86
43. Sauer, C.; Diele, S.; Lindner, N.; Tschierske, C. Liq. Cryst. 1998, 25, 109-116
44. For bent polycatenar dithiolium salts formation of columnar phases was reported, where the organization of the molecules inside the columns is more driven by the amphiphatic feature of these salts than by the shape of the molecules: Artzner, F.; Veber, M.; Clerc, M.; Levelut, A. M. Liq. Cryst. 1997, 23, 27-33
45. Weissflog, W. in; Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H.-W.; Vill, V. Handbook of Liquid Crystals; Wiley-VCH: Weinheim, Germany, 1998; Vol. 2B, pp 835 - 863.
46. Lee, M.; Cho, B.-K.; Zin, W.-C. Chem. Rev. 2001, 101, 3869-3892
47. Lee, M.; Yoo, Y.-S. J. Mater. Chem. 2002, 12, 2161-2168
48. Ryu, J.-H.; Cho, B.-K.; Lee, M. Bull. Korean Chem. Soc. 2006, 27, 1270-1282
49. Ryu, J.-H.; Lee, M. Struct. Bonding (Berlin) 2008, 128, 63-98
50. Nishikawa, E.; Samulski, E. T. Liq. Cryst. 2000, 27, 1463-1471
51. Guillevic, M.-A.; Bruce, D. W. Liq. Cryst. 2000, 27, 153-156
52. Lose, D.; Diele, S; Pelzl, G.; Dietzmann, E.; Weissflog, W. Liq. Cryst. 1998, 24, 707-717
53. Reddy, R. A.; Tschierske, C. J. Mater. Chem. 2006, 16, 907-961
54. Takezoe, H.; Takanishi, Y. Jpn. J. Appl. Phys. 2006, 45, 597-625
55. Pegenau, A.; Hegmann, T.; Tschierske, C.; Diele, S. Chem.-Eur. J. 1999, 5, 1643-1660
56. Pegenau, A.; Cheng, X. H.; Tschierske, C.; Göring, P.; Diele, S. New J. Chem. 1999, 23, 465-467
57. Cheng, X. H.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. 2000, 39, 592-595
58. Rosen, B. M.; Wilson, C. J.; Wilson, D. A.; Peterca, M.; Imam, M. R.; Percec, V. Chem. Rev. 2009, 109, 6275-6540
59. Borisch, K.; Diele, S.; Göring, P.; Kresse, H.; Tschierske, C. J. Mater. Chem. 1998, 8, 529-543
60. Fuchs, P.; Tschierske, C.; Raith, K.; Das, K.; Diele, S. Angew. Chem., Int. Ed. 2002, 41, 628-631
61. Cheng, X. H.; Das, K.; Diele, S.; Tschierske, C. Langmuir 2002, 18, 6521-6529
62. Kohlmeier, A.; Janietz, D. Chem. Mater. 2006, 18, 1483-1489
63. Seddon, J. M.; Templer, R. H. In Handbook of Biological Physics; Lipowsky, R.; Sackmann, E., Eds.; Elsevier: Amsterdam, The Netherlands, 1995; Vol. 1, pp 97 - 160.
64. Hassan, S.; Rowe, W.; Tiddy, G. J. T. In Handbook of Applied Surface and Colloid Chemistry; Holmberg, K., Ed.; Wiley: Chichester, U.K., 2002; Vol. 1, pp 465 - 508.
65. Hyde, S. T Identification of lyotropic liquid crystalline mesophases. In Handbook of Applied Surface and Colloid Science; Holmberg, K., Ed.; Wiley: Chichester, U.K., 2002; Vol. 2, pp 299 - 332.
66. Tschierske, C. J. Mater. Chem. 1998, 8, 1485-1508
67. Tschierske, C. J. Mater. Chem. 2001, 11, 2647-2671
68. Ostrovskii, B. I. In Structure and Bonding. Liquid Crystals I; Mingos, D. M. P., Ed.; Springer: Berlin, Germany, 1999; Vol. 94, pp 199 - 240.
69. Donnio, B.; Heinrich, B.; Allouchi, H.; Kain, J.; Diele, S.; Guillon, D.; Bruce, D. W. J. Am. Chem. Soc. 2004, 126, 15258-15268
70. Tschierske, C. Chem. Soc. Rev. 2007, 36, 1930-1970
71. Kölbel, M.; Beyersdorff, T.; Cheng, X. H.; Tschierske, C.; Kain, J.; Diele, S. J. Am. Chem. Soc. 2001, 123, 6809-6818
72. Cheng, X. H.; Prehm, M.; Das, M. K.; Kain, J.; Baumeister, U.; Diele, S.; Leine, D.; Blume, A.; Tschierske, C. J. Am. Chem. Soc. 2003, 125, 10977-10996
73. Cheng, X.-H.; Das, M. K.; Baumeister, U.; Diele, S.; Tschierske, C. J. Am. Chem. Soc. 2004, 126, 12930-12940
74. Prehm, M.; Götz, G.; Bäuerle, P.; Liu, F.; Zeng, X.; Ungar, G.; Tschierske, C. Angew. Chem., Int. Ed. 2007, 46, 7856-7859
75. Prehm, M.; Liu, F.; Baumeister, U.; Zeng, X.; Ungar, G.; Tschierske, C. Angew. Chem., Int. Ed. 2007, 46, 7972-7975
76. Prehm, M.; Enders, C.; Anzahaee, M. Y.; Glettner, B.; Baumeister, U.; Tschierske, C. Chem.-Eur. J. 2008, 14, 6352-6368
77. Cheng, X.; Dong, X.; Huang, R.; Zeng, X. B.; Ungar, G.; Prehm, M.; Tschierske, C. Chem. Mater. 2008, 20, 4729-4738
78. Glettner, B.; Liu, F.; Zeng, X. B.; Prehm, M.; Baumeister, U.; Walker, M.; Bates, M. A.; Boesecke, P.; Ungar, G.; Tschierske, C. Angew. Chem., Int. Ed. 2008, 47, 9063-9066
79. Chen, B.; Zeng, X.-B.; Baumeister, U.; Diele, S.; Ungar, G.; Tschierske, C. Angew. Chem., Int. Ed. 2004, 43, 4621-4625
80. Chen, B.; Zeng, X.-B.; Baumeister, U.; Ungar, G.; Tschierske, C. Science 2005, 307, 96-99
81. Chen, B.; Baumeister, U.; Pelzl, G.; Das, M. K.; Zeng, X.-B.; Diele, S.; Ungar, G.; Tschierske, C. J. Am. Chem. Soc. 2005, 127, 16578-16591
82. Cook, A. G.; Baumeister, U.; Tschierske, C. J. Mater. Chem. 2005, 15, 1708-1721
83. Liu, F.; Chen, B.; Baumeister, U.; Zeng, X.; Ungar, G.; Tschierske, C. J. Am. Chem. Soc. 2007, 129, 9578-9579
84. Liu, F.; Chen, B.; Glettner, B.; Prehm, M.; Das, M. K.; Baumeister, U.; Zeng, X. B.; Ungar, G.; Tschierske, C. J. Am. Chem. Soc. 2008, 130, 9666-9667
85. Prehm, M.; Liu, F.; Zeng, X. B.; Ungar, G.; Tschierske, C. J. Am. Chem. Soc. 2008, 130, 14922-14923
86. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
87. Kroon, R.; Lenes, M.; Hummelen, J. C.; Blom, P. W. M.; De Boer, B. Polym. Rev. 2008, 48, 531-582
88. Cheng, Y. J.; Yang, S.-H.; Hsu, C.-S. Chem. Rev. 2009, 109, 5868-5923
89. Kaeser, A.; Schenning, A. P. H. J. Adv. Mater. 2010, 22, 2985-2997
90. Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513-519
91. Hird, M.; Gray, G. W.; Toyne, K. J. Mol. Cryst. Liq. Cryst. 1991, 206, 187-204
92. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483
93. Prehm, M.; Diele, S.; Das, M. K.; Tschierske, C. J. Am. Chem. Soc. 2003, 125, 614-615
94. Due to the presence of the stereogenic centers in the two glycerol groups, and for compounds 1 also at the branching points in the lateral chains, the investigated systems actually represent racemic mixtures of several stereoisomers.
95. Immirzi, A.; Perini, B. Acta Crystallogr., Sect. A 1977, 33, 216-218
96. F segments on the mesophase stability of compounds 1 (Table 1) with only one fluorinated branch
97. hex = 3.8-4.1 nm were found: Kieffer, R.; Prehm, M.; Glettner, B.; Pelz, K.; Baumeister, U.; Liu, F.; Zeng, X. B.; Ungar, G.; Tschierske, C. Chem. Commun. 2008, 3861-3863
98. cell is about four for the hexagonal honeycombs formed by these compounds. (39)
99. Wang, Y.-J.; Carlisle, G. O. J. Mater. Sci.: Mater. Electron. 2002, 13, 173-178
100. Frank, H. S.; Wen, W.-Y. Disc. Farad. Soc. 1957, 24, 133-140
101. Bellamy, L. J.; Pace, R. L. Spectrochim. Acta 1966, 525-534
102. Kleeberg, H. In Intermolecular Forces, An Introduction to Modern Methods and Results; Huyskens, P. L.; Luck, W. A. P.; Zeegers- Huyskens, T., Eds.; Springer: Berlin, Germany, 1992; pp 251 - 280.
103. Shcherbina, M. A.; Zeng, X. B.; Tadjiev, T.; Ungar, G.; Eichhorn, S. H.; Phillips, K. E. S.; Katz, T. J. Angew. Chem., Int. Ed. 2009, 48, 7837-7840
104. -1, see Figure S3, Supporting Information). The precise structure of this mesophase M, though it is clearly a LC phase (maintenance of the diffuse wide angle scattering), has not yet been resolved.
105. T-shaped rod-coil molecules with lateral coils but without terminal groups were also reported recently, however these molecules show a different self assembly behavior (stepped stripes) as there is no attractive end-to-end interaction, which is essential for the formation of the polygonal cylinder phases and the rod-bundle phases, see Hong, D.-J.; Lee, E.; Lee, J.-K.; Zin, W.-C.; Han, M.; Sim, E.; Lee, M. J. Am. Chem. Soc. 2008, 130, 14448-14449
106. A R 3 m phase was recently also observed for the organization of functionalized gold nanoparticles in a calamitc nematic matrix. In this case the 3D packing is provided by the optimization of the packing of the nanoparticles in the nematic director field: Zeng, X. B.; Liu, F.; Fowler, A. G.; Ungar, G.; Cseh, L.; Mehl, G. H. J.; Macdonald, E. Adv. Mater. 2009, 21, 1746-1750
107. An orthorhombic LC phase with columnar elements has been reported in dendrimers, space group Pmna: Rosen, B. M.; Peterca, M.; Huang, C.; Zeng, X. B.; Ungar, G.; Percec, V. Angew. Chem., Int. Ed. 2010, 49, 7002-7005
108. Pershan, P. S. Structure of Liquid Crystal Phases; World Scientific: Singapore, 1988.
109. Veerman, J. A. C.; Frenkel, D. Phys. Rev. A 1991, 43, 4334-4343
110. de Genns, P. J.; Prost, J. Physics of Liquid Crystals; Oxford Science Publishers: Oxford, England, 1975.
111. Cheng, X. H.; Das, M. K.; Diele, S.; Tschierske, C. Angew. Chem., Int. Ed. 2002, 41, 4031-4035
112. Prehm, M.; Cheng, X. H.; Diele, S.; Das, M. K.; C. Tschierske, C. J. Am. Chem. Soc. 2002, 124, 12072-1273
113. Patel, N. M.; Dodge, M. R.; Zhu, M. H.; Petschek, R. G.; Rosenblatt, C.; Prehm, M.; Tschierske, C. Phys. Rev. Lett. 2004, 92, 015501
114. Patel, N. M.; Syed, I. M.; Rosenblatt, C.; Prehm, M.; Tschierske, C. Liq. Cryst. 2005, 32, 55
115. Fu, K.; Sekine, N.; Sone, M.; Tokita, M.; Watanabe, J. Polymer J. 2002, 34, 291-297
116. Carbonnier, B.; Andreopoulou, A. K.; Pakula, T. J.; Kallitis, K. Macromol. Chem. Phys. 2005, 206, 66-76
117. Kim, L.; Arnt, T.; Atkins, E.; Tew, G. N. Chem.-Eur. J. 2006, 12, 2423-2427
118. Riala, P.; Andreopoulou, A.; Kallitsis, J.; Gitsas, A.; Floudas, G. Polymer 2006, 47, 7241-7250
119. Rieth, S.; Baddeley, C.; Badjic, J. D. Soft Matter 2007, 3, 137-154
120. Supramolecular Polymers, 2nd ed.; Ciferri, A., Ed.; Marcel Dekker, Inc.: New York, 2006
121. Hoogenboom, R.; Schubert, U. S. Chem. Soc. Rev. 2006, 35, 622-629
122. Rowan, S. J.; Mather, P. T. Struct. Bonding (Berlin) 2008, 128, 119-149
123. Ungar, G. Polymer 1993, 34, 2050-2059
124. Zheng, R.-Q.; Chen, E.-Q.; Cheng, S. Z. D.; Xie, F.; Yan, D.; He, T.; Percec, V.; Chu, P.; Ungar, G. Macromolecules 1999, 32, 3574-3582
125. Watanabe, J.; Sekine, N.; Nematsu, T.; Sone, M.; Kricheldorf, H. R. Macromolecules 1996, 29, 4816-4818
126. Petty, M. C. Molecular Electronics. From Principles to Practice; Wiley: New York, 2008.
127. Funahashi, M.; Shimura, H.; Yoshio, M.; Kato, T. Struct. Bonding (Berlin) 2008, 128, 151-179
128. Pankaj, S.; Beiner, M. Soft Matter 2010, 6, 3506-3516
129. Kreyes, A.; Ellinger, S.; Landfester, K.; Defaux, M.; Ivanov, D. A.; Elschner, A.; Meyer-Friedrichsen, T.; Ziener, U. Chem. Mater. 2010, 22, 2079-2092