Columnar mesophases controlled by counterions in potassium complexes of dibenzo[18]crown-6 derivatives

Chemistry - A European Journal

Volumn 15, Issue 37, 2009, Pages 9530-9542

  Kaller, Martin ^a   Tussetschläger, Stefan ^a   Fischer, Peter ^a   Deck, Christopher ^a   Baro, Angelika ^a   Giesselmann, Frank ^a   Laschat, Sabine ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Anions; Crown compounds; Ion pairs; Liquid crystals; Mesophases

Indexed keywords

18-CROWN-6; ANIONS; COLUMNAR MESOPHASES; COUNTERIONS; CROWN COMPOUNDS; HIGH ORDER; ION PAIRS; MALDI-TOF; MESOMORPHIC PROPERTY; MESOPHASE STABILIZATION; MESOPHASES; NMR SIGNALS; NMR SPECTROSCOPY; NMR SPECTRUM; O-TERPHENYL; PHASE WIDTH; PLASTIC CRYSTAL PHASE; POLARIZING OPTICAL MICROSCOPY; POTASSIUM COMPLEX; XRD;

COMPLEXATION; CRYSTALS; DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTALS; NEGATIVE IONS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL MICROSCOPY;

CHLORINE COMPOUNDS;

EID: 70349289401     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901173     Document Type: Article

References (104)

1. a) X. Zhang, N. Zhao, S. Liang, X. Lu, X. Li, Q. Xie, X. Zhang, J. Xu, Adv. Mater. 2008, 20, 2938-2946;
2. b)J.F. Mano, Adv. Eng. Mater. 2008, 10, 515-527;
3. c) A. Richter, G. Paschew, S. Klatt, J. Lienig, K.-F. Arndt, H.-J. P.Adler, Sensors 2008, 8, 561-581;
4. d) H.-J. Kim, Y-B. Lim, M. Lee, J. Polym. Sci. Polym. Chem. Ed. 2008, 46, 1925-1935;
5. e) B. G. Trewyn, S. Giri, I.I. Slowing, V.S.-Y. Lin, Chem. Commun. 2007, 3236-3245;
6. f) Y. Lu, J. Liu, Acc. Chem. Res. 2007, 40, 315-323;
7. g)A.J. Wilson, Soft Matter 2007, 3, 409-425;
8. h) S. Rieth, C. Baddeley, J. D. Badjic, Soft Matter 2007, 3, 137-154;
9. i) M. Behl, A. Lendlein, Soft Matter 2007, 3, 58-67.
10. Reviews: a) K. Praefcke, A. Eckert, Mol. Cryst. Liq. Cryst. 2003, 396, 265-299;
11. b)K. Praefcke, D. Singer in Handbook of Liquid Crystals, Vol.2B (Eds.: D. Demus, J. Goodby, G.W. Gray, H.-W. Spiess, V. Vi1l), Wiley-VCH, Weinheim, 1998, pp. 945-967;
12. c) K. Praefcke, J. D. Holbrey, J. Inclusion Phenom. Mol. Recognit. Chem. 1996, 24, 19-41;
13. d) K. Praefcke, D. Singer, Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. C 1994, 3, 265-270.
14. Reviews: a) S. Pieraccini, A. Ferrarini, G. P.Spada, Chirality 2008, 20, 749-759;
15. b) G. Gottarelli, GP.Spada, Top. Stereochem 2003, 24, 425-455;
16. c)H.-D. Dörfler, Adv. Colloid Interface Sci. 2002, 98, 285-340;
17. d)H.-M.P.Chen, S.W. Culligan, Y.H. Geng, D. Katsis, S. H. Chen, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 2002, 43, 145-146;
18. e) H.-G. Kuball, E. Dorr, EMIS Datarev. Ser. 2000, 25, 333-343;
19. f) G. Gottarelli, G.P.Spada, G. Solladie, Nouv. J. Chim. 1986, 10, 691-696;
20. g) G. P.Spada, G. Proni, Enantiomer 1998, 3, 301-314.
21. Reviews: a) R. P.Lemieux, Chem. Soc. Rev. 2007, 36, 2033-2045;
22. b) C. S. Hartley, N. Kapemaum, J. C. Roberts, F. Giesselmann, R. P.Lemieux, J. Mater. Chem. 2006, 16, 2329-2337;
23. c) R. P.Lemieux, Acc. Chem. Res. 2001, 34, 845-853;
24. d) S.T. Lagerwall, Ferroelectric and Antiferroelectric Liquid Crystals, Wiley-VCH, Weinheim, 1999;
25. e)J.W. Goodby, R. Blinc, N. A. Clark, S. T. Lagerwall, M. A. Osipov, S. A. Pikin, T. Sakurai, K. Yoshino, B. Zeks, Ferroelectric Liquid Crystals: Principles, Properties and Applications, Gordon and Breech, Philadelphia 1991.
26. a) R. P.Tuffin, G. H. Mehl, K. J. Toyne, J. W. Goodby, Mol. Cryst. Liq. Cryst. 1997, 304, 223-230;
27. b) R. P.Tuffin, K. J. Toyne, J. W. Goodby, J. Mater. Chem. 1996, 6, 1271-1282;
28. c)R.P.Tuffin, K.J. Toyne, J. W. Goodby, J. Mater. Chem. 1995, 5, 2093-2104;
29. d)A.J. Blake, D. W. Bruce, J. P.Danks, I. A. Fallis, D. Guillon, S. A. Ross, H. Richtzenhain, M. Schröder, J. Mater. Chem. 2001, 11, 1011-1018;
30. e)J. A. Schröter, C. Tschierske, M. Wittenberg, J.H. Wendorff, Angew. Chem. 1997, 109, 1160-1163;
31. Angew. Chem Int. Ed. Engl. 1997, 30, 1119-1121.
32. a) V. Percec, D. Schlueter, G. Ungar, S. Z. D. Cheng, A. Zhang, Macromolecules 1998, 31, 1745-1762;
33. b) V. Percec, G. Johansson, G. Ungar, J. Zhou, J. Am. Chem. Soc. 1996, 118, 9855-9866;
34. c)V. Percec, D. Tomazos, J. Heck, H. Blackwell, G. Ungar, J. Chem. Soc. Perkin Trans. 2 1994, 31-44;
35. d) G. Johansson, V. Percec, G. Ungar, D. Abramic, J. Chem. Soc. Perkin Trans. 1 1994, 447-459;
36. e)V. Percec, G. Johansson, J. Heck, G. Ungar, S. V Batty, J. Chem. Soc. Perkin Trans. 1 1993, 1411-1420;
37. f) V. Percec, G. Johansson, R. Rodenhouse, Macromolecules 1992, 25, 2563-2565.
38. a) S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hagele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, M. Tosoni, Angew. Chem. 2007, 119, 4916-4973;
39. Angew. Chem. Int. Ed. 2007, 46, 4832-4887;
40. b) S. Sergeyev, W. Pisula, Y H. Geerts, Chem. Soc. Rev. 2007, 36, 1902-1929;
41. c) M. Peterca, V. Percec, A. E. Dulcey, S. Nummelin, S. Korey, M. Hies, P.A. Heiney, J. Am. Chem. Soc. 2006, 128, 6713-6720;
42. d) T. Kato, N. Mizoshita, K. Kishimoto, Angew. Chem. 2006, 118, 44-74;
43. Angew. Chem. Int. Ed. 2006, 45, 38-68;
44. e) C. Tschierske, Annu. Rep. Prog. Chem. 2001, 97, 191-267;
45. f) C. Tschierske, J. Mater. Chem. 1998, 8, 1485-1508;
46. g) J. W. Goodby, G. H. Mehl, I. M. Saez, R. P.Tuffin, G. Mackenzie, R. Auzély-Velty, T. Benvegnu, D. Plusquellec, Chem. Commun. 1998, 2057-2070.
47. a) U. Beginn, G. Zipp, M. Möller, Adv. Mater. 2000, 12, 510-513;
48. b) U. Beginn, G. Zipp, A. Mourran, P.Walther, M. Möller, Adv. Mater. 2000, 12, 513-516;
49. c) U. Beginn, G. Zipp, M. Möller, Chem. Eur. J. 2000, 6, 2016-2023.
50. Y. Chen, W. Su, M. Bai, J. Jiang, X. Li, Y. Liu, L. Wang, S. Wang, J. Am. Chem. Soc. 2005, 127, 15700-15701.
51. a) C. F. van Nostrum, Adv. Mater. 1996, 8, 1027-1030;
52. b) C. F. van Nostrum, R. J.M. Nolte, Chem. Commun. 1996, 2385-2392;
53. c) C.F. van Nostrum, S. J. Picken, A.-J. Schouten, R. J. M. Nolte, J. Am. Chem. Soc. 1995, 117, 9957-9965;
54. d) C. F. van Nostrum, S. J. Picken, R. J. M. Nolte, Angew. Chem. 1994, 106, 2298-2300;
55. Angew. Chem. Int. Ed. Engl. 1994, 33, 2173-2175;
56. e) O. E. Sielcken, M. M. van Tilborg, M. F. M. Roks, R. Hendriks, W. Drenth, R. J. M. Nolte, J. Am. Chem. Soc. 1987, 109, 4261-4265;
57. f) C. Sirlin, L. Bosio, J. Simon, V. Ahsen, E. Yilmazer, Ö. Bekaroglu, Chem. Phys. Lett. 1987, 139, 362-364.
58. a) M. Gutiérrez-Nava, M. Jaeggy, H. Nierengarten, P.Masson, D. Guillon, A. Van Dorsselaer, J.-F. Nierengarten, Tetrahedron Lett. 2003, 44, 3039-3042;
59. b) P.Samorí, H. Engelkamp, P.de Witte, A. E. Rowan, R. J. M. Nolte, J. P.Rabe, Angew. Chem. 2001, 113, 2410-2412;
60. Angew. Chem. Int. Ed. 2001, 40, 2348-2350;
61. c) H. Engelkamp, S. Middelbeek, R. J. M. Nolte, Science 1999, 284, 785-788.
62. a)D.J. Abdallah, R. G. Weiss, Adv. Mater. 2000, 12, 1237-1247;
63. b) K. Murata, M. Aoki, T. Nishi, A. Ikeda, S. Shinkai, J. Chem. Soc. Chem. Commun. 1991, 1715-1718.
64. N Steinke, W. Frey, A. Baro, S. Laschat, C. Drees, M. Nimtz, C. Hagele, F. Giesselmann, Chem. Eur. J. 2006, 12, 1026-1035.
65. N Steinke, M. Jahr, M. Lehmann, A. Baro, W. Frey, S. Tussetschläger, S. Sauer, S. Laschat, J. Mater. Chem. 2009, 19, 645-654.
66. A. Schultz, S. Laschat, A. Saipa, F. Giesselmann, M. Nimtz, J. L. Schulte, A. Baro, B. Miehlich, Adv. Funct. Mater. 2004, 14, 163-168.
67. S. Mochizuki, A. Wakisaka, J. Phys Chem. A 2002, 106, 5095-5100.
68. U. Olsher, J. Am. Chem. Soc. 1982, 104, 4006-4007.
69. a)M. J. Sienkowska, J. M. Farrar, F. Zhang, S. Kusuma, P.A. Heiney, P.Kaszynski, J. Mater. Chem. 2007, 17, 1399-1411;
70. b) A. R. Surrey, L. I. Smith, C.-P. Lo, Org. Synth. 1946, 26, 90.
71. N.D. Lowe, C.D. Garner, J. Chem. Soc. Dalton Trans. 1993, 2197-2207.
72. Reviews: a) C.J. Pedersen, J.-M. Lehn, D. J. Cram, Resonance 2001, 6, 71-79;
73. b) J.-M. Lehn, Angew. Chem. 1988, 100, 91-116;
74. Angew. Chem. Int. Ed. Engl. 1988, 27, 89-112;
75. c) D. J. Cram, Angew. Chem. 1988, 100, 1041-1052;
76. Angew. Chem. Int. Ed. Engl. 1988, 27, 1009-1020;
77. d)C.J. Pedersen, Angew. Chem. 1988, 100, 1053-1059;
78. Angew. Chem. Int. Ed. Engl. 1988, 27, 1021-1027.
79. a)M. d'Amboise, D. Noel, Anal. Chim. Acta 1985, 170, 255-264;
80. b) H. Sato, Y Kusumoto, Chem. Lett. 1978, 635-638.
81. D. Live, S. I. Chan, J. Am. Chem. Soc. 1976, 98, 3769-3778.
82. J. C. Lockhart, A. C. Robson, M. E. Thompson, P. D. Tyson, I. H. M. Wallace, J. Chem. Soc. Dalton Trans. 1978, 611-617.
83. T. Sugawara, M. Yudasaka, Y. Yokoyama, T. Fujiyama, H. Iwamura, J. Phys. Chem. 1982, 86, 2705-2709.
84. M.-C. Fedarko, J. Magn. Reson. 1973, 12, 30-35.
85. a) J. D. Dunitz, M. Dobler, P.Seiler, R. P.Phizackerley, Acta Crystallogr. Sect. B 1974, 30, 2733-2738;
86. b) P.Seiler, M. Dobler, J. D. Dunitz, Acta Crystallogr. Sect. B 1974, 30, 2744-2745.
87. P.Dapporto, P.Paoli, I. Matijašic, L. Tušek-Božic, Inorg. Chim. Acta 1996, 252, 383-389.
88. A. Bianchi, J. Giusti, P.Paoletti, S. Mangani, Inorg. Chim. Acta 1986, 117, 157-164.
89. a) J. M. Harrington, S. B. Jones, P.H. White, R. D. Hancock, Inorg. Chem. 2004, 43, 4456-4463;
90. b) J. Dou, X. Gao, F. Dong, D. Li, D. Wang, Dalton Trans. 2004, 2918-2922;
91. c)D.-C. Li, Z.-X. Li, J.-M. Dou, D.-Q. Wang, J. Inclusion Phenom. Macrocyclic Chem. 2003, 46, 83-88;
92. d) H. Zhang, X. Wang, B. K. Teo, J. Am. Chem. Soc. 1996, 118, 11813-11821.
93. L. C. Manege, T. Takayanagi, M. Oshima, S. Motomizu, Analyst 2000, 125, 699-703.
94. S. Krishna Prasad, D. S. S. Rao, S. Chandrasekhar, S. Kumar, Mol. Cryst. Liq. Cryst. 2003, 396, 121-139.
95. A.M. Levelut, J. Chim. Phys. Phys.-Chim. Biol. 1983, 80, 149-161.
96. N. F. M. Henry, K. Lonsdale, International Tables for X-Ray Crystallography, Kynoch Press, Birmingham, 1965.
97. M. Lehmann, C.Köhn, H. Meier, S. Renker, A. Oehlhof, J. Mater. Chem. 2006, 16, 441-451.
98. ChemBio3D Ultra 11.0, Cambridge Soft, 2007.
99. H. Zheng, C.K. Lai, T.M. Swager, Chem. Mater. 1995, 7, 2067-2077.
100. C.K. Lai, C-H. Tsai, Y-S. Pang, J. Mater. Chem. 1998, 8, 1355-1360.
101. a) XACQ 4.0.4;
102. b) XMASS/XTOF 5.1.0, Bruker Daltonics.
103. SAXS 4.1.26, Bruker AXS, 2001.
104. A. Schultz, Dissertation, Technische Universität Braunschweig (Germany), 2003.