Supramolecular dendrimers: Unusual mesophases of ionic liquid crystals derived from protonation of DAB dendrimers with facial amphiphilic carboxylic acids

Journal of Materials Chemistry

Volumn 15, Issue 17, 2005, Pages 1708-1721

  Cook, Andrew G ^a   Baumeister, Ute ^a   Tschierske, Carsten ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; CHEMICAL MODIFICATION; ENZYMES; LIQUID CRYSTALS; MOLECULAR STRUCTURE; POLYETHERS; SELF ASSEMBLY; STRUCTURE (COMPOSITION); SUPRAMOLECULAR CHEMISTRY;

ALKYL CHAINS; IONIC LIQUID CRYTSALS; IONIC SPECIES; PROTONATION;

DENDRIMERS;

EID: 18844370950     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415892j     Document Type: Article

References (109)

1. D. A. Tomalia and J. M. Frechet, J. Polym. Sci., Part A: Polym. Chem., 2002, 40, 2719.
2. (a) F. Zeng and S. C. Zimmerman, Chem. Rev., 1997, 97, 1681;
3. (b) S. M. Grayson and J. M. Frechet, Chem. Rev., 2001, 101, 3819.
4. G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendrimers and Dendrons: Concepts, Synthesis and Perspectives, Wiley-VCH, Weinheim, 2001.
5. U. Boas and P. M. H. Heegaard, Chem. Soc. Rev., 2004, 33, 43.
6. S.-E. Stiriba, H. Frey and R. Haag, Angew. Chem., Int. Ed., 2002, 41, 1329.
7. (a) P. C. J. Kamer, P. W. N. M. van Leeuwen and J. N. H. Reek, Chem. Rev., 2002, 102, 3717;
8. (b) L. J. Twyman, A. S. H. King and I. K. Martin, Chem. Soc. Rev., 2002, 31, 69.
9. (a) D. Astruc and F. Chardac, Chem. Rev., 2001, 101, 2991;
10. (b) R. M. Crooks, M. Zhao, L. Sun, V. Chechik and L. K. Yeung, Acc. Chem. Res., 2001, 34, 181;
11. L. J. Twyman, A. S. H. King and I. K. Martin, Chem. Soc. Rev., 2002, 31, 69.
12. (a) J. M. Frechet, J. Polym. Sci., Part A: Polym. Chem., 2003, 41, 3713;
13. (b) J. M. J. Frechet, Proc. Natl. Acad. Sci. USA, 2002, 99, 4782.
14. V. Percec, A. E. Dulcey, V. S. K. Balagurusamy, Y. Miura, J. Smidrkal, M. Peterca, S. Nummelin, U. Edlund, S. D. Hudson, P. A. Heiney, H. Duan, S. N. Magonov and S. A. Vinogradov, Nature, 2004, 430, 764.
15. (a) V. V. Narayanan and G. R. Newkome, Top. Curr. Chem., 1998, 19;
16. (b) D. A. Tomalia and I. Majoros, J. Macromol. Sci., Rev. Macromol Chem., 2003, 43, 411.
17. (a) S. A. Ponomarenko, N. I. Boiko and V. P. Shibaev, Polym. Sci. Ser. C, 2001, 43, 1;
18. (b) D. Guillon and R. Deschenaux, Curr. Opin. Solid State Mater. Sci., 2002, 6, 515;
19. J. A. A. W. Elemans, M. J. Boerakker, S. J. Holder, A. E. Rowan, W.-D. Cho, V. Percec and R. J. M. Nolle, Proc. Natl. Acad. Sci. USA, 2002, 99, 5093.
20. (a) V. S. K. Balagurusamy, G. Ungar, V. Percec and G. Johansson, J. Am. Chem. Soc., 1997, 119, 1539;
21. (b) V. Percec, W. D. Cho, M. Möller, S. A. Prokhorova, G. Ungar and D. J. P. Yeardley, J. Am. Chem. Soc., 2000, 122, 4249;
22. (c)V. Percec, W. D. Cho and G. Ungar, J. Am. Chem. Soc., 2000, 122, 10273;
23. (d)V. Percec, W. D. Cho, G. Ungar and D. J. P. Yeardley, J. Am. Chem. Soc., 2001, 123, 1302;
24. (e) V. Percec, C. M. Mitchell, W.-D. Cho, S. Uchida, M. Glodde, G. Ungar, X. Zeng, Y. Liu, V. S. K. Balagurusamy and P. A. Heiney, J. Am. Chem. Soc., 2004, 126, 6078.
25. (a) U. Stebani and G. Lattermann, Adv. Mater., 1995, 7, 578;
26. (b) J. H. Cameron, A. Facher, G. Latterman and S. Diele, Adv. Mater., 1997, 9, 398.
27. M. Seitz, T. Plesnivy, K. Schimossek, M. Edelmann, H. Ringsdorf, H. Fischer, H. Uyama and S. Kobayashi, Macromolecules, 1996, 29, 6560.
28. (a) K. Lorenz, H. Frey, B. Stühn and R. Mülhaupt, Macromolecules, 1997, 30, 6860;
29. (b) K. Lorenz, D. Hölter, R. Mühlhaupt and H. Frey, Adv. Mater., 1996, 8, 414.
30. D. Tsiourvas, K. Stathopoulou, Z. Sideratou and C. M. Paleos, Macromolecules, 2002, 35, 1746.
31. (a) K. Borisch, S. Diele, P. Göring, H. Müller and C. Tschierske, Liq. Cryst., 1997, 22, 427;
32. (b) K. Borisch, S. Diele, P. Göring, H. Kresse and C. Tschierske, J. Mater. Chem., 1998, 8, 529.
33. (a) G. J. T. Tiddy, Phys. Rep., 1988, 57, 1;
34. (b) J. M. Seddon and R. H. Templer, in Handbook of Biological Physics, ed. R. Lipowsky and E. Sackmann, Elsevier, Amsterdam, 1995, vol. 1, p. 97;
35. S. Hassan, W. Rowe and G. J. T. Tiddy, in Handbook of Applied Surface and Colloid Chemistry, ed. K. Holmberg, Wiley, Chichester, 2002, vol. 1, p 465.
36. G. Ungar, Y. Liu, X. Zeng, V. Percec and W. D. Cho, Science, 2003, 299, 1208.
37. X. Zeng, G. Ungar, Y. Liu, V. Percec, A. E. Dulcey and J. K. Hobbs, Nature, 2004, 428, 157.
38. (a) J. W. Goodby, G. H. Mehl, I. M. Saez, R. P. Tuffin, G. Mackenzie, R. Auzely-Velty, T. Benvegnu and D. Plusquellec, Chem. Commun., 1998, 2057.
39. K. Yonetake, T. Masuko, T. Morishita, K. Suzuki, M. Ueda and R. Nagahata, Macromolecules, 1999, 32, 6578.
40. M. W. P. L. Baars, S. H. M. Söntjens, H. M. Fischer, H. W. I. Peerlings and E. W. Meijer, Chem.-Eur. J., 1998, 4, 2456.
41. J. Barbera, M. Marcos and J. L. Serrano, Chem.-Eur. J., 1999, 5, 1834.
42. (a) S. A. Ponomarenko, E. A. Rebrov, Y. Bobronsky, N. I. Boiko, A. M. Muzafarov and V. P. Shibaev, Liq. Cryst., 1996, 21, 1;
43. (b) E. I. Ryumtsev, N. P. Evlampieva, A. V. Lezov, S. A. Ponomarenko, N. I. Boiko and V. P. Shibaev, Liq. Cryst., 1998, 25, 475;
44. S. A. Ponomarenko, E. A. Rebrov, N. I. Boiko, A. M. Muzafarov and V. P. Shibaev, Polym. Sci. Ser. A, 1998, 40, 763.
45. A. Sunder, M.-F. Quincy, R. Mülhaupt and H. Frey, Angew. Chem., Int. Ed., 1999, 38, 2928.
46. (a) P. Busson, H. Ihre and A. Hull, J. Am. Chem. Soc., 1998, 120, 9070;
47. (b) P. Busson, J. Örtegren, H. Ihre, U. W. Gedde, A. Huit and G. Andersson, Macromolecules, 2001, 34, 1221;
48. P. Busson, J. Örtegren, H. Ihre, U. W. Gedde, A. Huit, G. Andersson, A. Eriksson and M. Lindgren, Macromolecules, 2002, 35, 1663.
49. (a) V. Percec and M. Kawasumi, Macromolecules, 1992, 25, 1164;
50. (b) S. Bauer, H. Fischer and H. Ringsdorf, Angew. Chem., Int. Ed. Engl., 1993, 32, 1589;
51. (c)V. Percec, P. W. Chu and M. Kawasumi, Macromolecules, 1994, 27, 4441;
52. (d)S. W. Hanh, Y. K. Yun, J. I. Jin and O. H. Han, Macromolecules, 1998, 31, 6417;
53. (e) H. R. Kricheldorf, T. Stukenbrock and C. Friedrich, J. Polym. Sci.,Chem. Ed., 1998, 36, 1397.
54. (a) M. Marcos, R. Gimenez, J. L. Serrano, B. Donnio, B. Heinrich and D. Guillon, Chem.-Eur. J., 2001, 7, 1006;
55. (b) B. Donnio, J. Barbera, R. Gimenez, D. Guillon, M. Marcos and J. L. Serrano, Macromoelcules, 2002, 35, 370;
56. J.-M. Rueff, J. Barbera, B. Donnio, D. Guillon, M. Marcos and J.-L. Serrano, Macromolecules, 2003, 36, 8368;
57. M. Marcos, A. Omenat and J. L. Serrano, C. R. Chim., 2003, 6, 947.
58. S. A. Ponomarenko, N. I. Boiko, V. P. Shibaev, R. M. Richardson, I. J. Whitehouse, E. A. Rebrov and A. M. Muzafarov, Macromolecules, 2000, 33, 5549.
59. (a) C. Tschierske, J. Mater. Chem., 1998, 8, 1485;
60. (b) C. Tschierske, J. Mater. Chem., 2001, 11, 2647;
61. C. Tschierske, Curr. Opin. Colloid Interface Sci., 2002, 7, 69;
62. C. Tschierske, Annu. Rep. Progr. Chem., Sect. C: Phys. Chem., 2001, 97, 191.
63. L. Gehringer, C. Bourgogne, D. Guillon and B. Donnio, J. Am. Chem. Soc., 2004, 126, 3865.
64. J. Barbera, R. Gimenez, M. Marcos and J. L. Serrano, Liq. Cryst., 2002, 29, 309.
65. (a) I. M. Saez, J. W. Goodby and R. M. Richardson, Chem.-Eur. J., 2001, 7, 2758;
66. (b) I. M. Saez and J. W. Goodby, Chem.-Eur. J., 2003, 9, 4869;
67. I. M. Saez and J. W. Goodby, Liq. Cryst. Today, 2004, 13, 1.
68. (a) R. Plehnert, J. A. Schröter and C. Tschierske, J. Mater. Chem., 1998, 8, 2611;
69. (b) F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, M. Wittenberg and J. H. Wendorff, Adv. Mater., 1997, 9, 564;
70. J. A. Schröter, C. Tschierske, M. Wittenberg and J. H. Wendorff, Angew. Chem., Int. Ed. Engl., 1997, 36, 1119;
71. J. A. Schröter, C. Tschierske, M. Wittenberg and J. H. Wendorff, J. Am. Chem. Soc., 1998, 120, 10669.
72. B. Chen, U. Baumeister, S. Diele, M. K. Das, X. Zeng, G. Ungar and C. Tschierske, J. Am. Chem. Soc., 2004, 126, 8608.
73. B. Chen, X. B. Zeng, U. Baumeister, S. Diele, G. Ungar and C. Tschierske, Angew. Chem., 2004, 43, 4621.
74. B. Chen, X. B. Zeng, U. Baumeister, G. Ungar and C. Tschierske, Science, 2005, 307, 96.
75. (a) M. Kölbel, T. Beyersdorff, X. H. Cheng, C. Tschierske, J. Kain and S. Diele, J. Am. Chem. Soc., 2001, 123, 6809;
76. (b) X. H. Cheng, M. K. Das, S. Diele and C. Tschierske, Angew. Chem., Int. Ed., 2002, 41, 4031;
77. (c)M. Prehm, X. H. Cheng, S. Diele, M. K. Das and C. Tschierske, J. Am. Chem. Soc., 2002, 124, 12072;
78. (d)X. H. Cheng, M. Prehm, M. K. Das, J. Kain, U. Baumeister, S. Diele, D. Leine, A. Blume and C. Tschierske, J. Am. Chem. Soc., 2003, 125, 10977;
79. (e) M. Prehm, S. Diele, M. K. Das and C. Tschierske, J. Am. Chem. Soc., 2003, 125, 614;
80. (f) N. M. Patel, M. R. Dodge, M. H. Zhu, R. G. Petschek, C. Rosenblatt, M. Prehm and C. Tschierske, Phys. Rev. Lett., 2004, 92, 15501;
81. (g) X. H. Cheng, M. K. Das, U. Baumeister, S. Diele and C. Tschierske, J. Am. Chem. Soc., 2004, 126, 12930.
82. (a) T. Kato, N. Mizoshita and K. Kanie, Macromol. Rapid Commun., 2001, 22, 797;
83. (b) C. M. Paleos and D. Tsiourvas, Liq. Cryst., 2001, 28, 1127.
84. D. Tsiourvas, T. Felekis, Z. Sideratou and C. M. Paleos, Liq. Cryst., 2004, 31, 739.
85. Y. Tian, X. Xu, Y. Zhao, X. Tang and T. Li, Liq. Cryst., 1997, 22, 87.
86. Y. Nakatsuji, N. Kawamura, M. Okahara and K. Matsushima, Synthesis, 1981, 42.
87. M. Hird, G. W. Gray and K. J. Toyne, Mol. Cryst. Liq. Cryst., 1991, 206, 187.
88. J. P. Wolfe, R. A. Singer, B. H. Yang and S. L. Buchwald, J. Am. Chem. Soc., 1999, 121, 9550.
89. (a) J. C. Ma and D. A. Dougherty, Chem. Rev., 1997, 97, 1303;
90. (b) L. K. Tsou, C. D. Tatko and M. L. Waters, J. Am. Chem. Soc., 2002, 124, 14917.
91. (a) W. Weissflog, in Handbook of Liquid Crystals, ed. D. Demus, J. W. Goodby, G. W. Gray, H.-W. Spiess and V. Vill, Wiley-VCH, Weinheim, 1998; vol. 2B, p. 835;
92. (b) P. Judeinstein, P. Berdagué, J.-P. Bayle, N. Sinha and K. V. Ramanathan, Liq. Cryst., 2001, 28, 1691.
93. (a) S. V. Arehart and C. Pugh, J. Am. Chem. Soc., 1997, 119, 3027;
94. (b) A. C. Small, D. K. Hunt and C. Pugh, Liq. Cryst., 1999, 26, 849.
95. F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, R. Kleppinger and J. H. Wendorff, Angew. Chem., Int. Ed. Engl., 1995, 34, 1631.
96. squ phases developing in the contact region An+Gn by a change of birefringence (see, for example, Fig. 6c,d).
97. It was not possible to get a cubic (optically isotropic) mesophase for any of the discrete binary mixtures; alignment is concentration dependent, occasionally also in the usually dark areas birefringent mosaics can be found.
98. (a) J.-M. Lehn, Science, 2002, 295, 2400;
99. (b) J.-M. Lehn, Proc. Natl. Acad. Sci. USA, 2002, 99, 4763.
100. V. Percec, M. Glodde, T. K. Bera, Y. Miura, I. Shiyanovskaya, K. D. Singer, V. S. K. Balagurusamy, P. A. Heiney, I. Schnell, A. Rapp, H.-W. Spiess, S. D. Hudsonk and H. Duank, Nature, 2002, 419, 384.
101. (a) M. Antonietti and C. Göltner, Angew. Chem., Int. Ed. Engl., 1997. 36, 910;
102. (b) M. C. Holmes, Curr. Opin. Colloid Interface. Sci., 1998. 3, 485;
103. I. Koltover, T. Salditt, J. O. Radler and C. R. Safinya, Science, 1998, 281, 78.
104. Y. Cai, D. Wang, X. Hu, Y. Xu, Y. Zhao, J. Wu and D. Xu, Macromol. Rapid Commun., 2001, 22, 504.
105. C. F. J. Faul and M. Antonietti, Adv. Mater., 2003, 15, 673.
106. (a) F. Camerel, P. Strauch, M. Antonietti and C. F. J. Faul, Chem.-Eur. J., 2003, 9, 3764;
107. (b) Y. Gutan, Y. Zakrevskyy, J. Stumpe, M. Antonietti and C. F. J. Faul, Chem. Commun., 2003, 894;
108. F. Camerel and C. F. J. Faul, Chem. Commun., 2003, 1958;
109. J. Kadam, C. F. J. Faul and U. Scherf, Chem. Mater., 2004, 16, 3867.