Triblock polyphiles through click chemistry: Self-assembled thermotropic cubic phases formed by micellar and monolayer vesicular aggregates

Chemistry - A European Journal

Volumn 19, Issue 48, 2013, Pages 16303-16313

  Tan, Xiaoping ^a   Kong, Leiyang ^a   Dai, Heng ^a   Cheng, Xiaohong ^a   Liu, Feng ^b   Tschierske, Carsten ^c  

^a YUNNAN UNIVERSITY   (China)

^b XI'AN JIAOTONG UNIVERSITY   (China)

^c MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

click chemistry; liquid crystals; phase transitions; self assembly; triblock polyphiles

Indexed keywords

ALKYL CHAIN LENGTHS; CLICK CHEMISTRY; MESOPHASE BEHAVIOR; POLARIZING OPTICAL MICROSCOPY; SPHERICAL AGGREGATES; THERMOTROPIC CUBIC PHASIS; TRIBLOCKS; VESICULAR AGGREGATES;

DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTALS; MOLECULES; MONOLAYERS; NITROGEN COMPOUNDS; PHASE TRANSITIONS; SELF ASSEMBLY; SPHERES; SYNTHESIS (CHEMICAL);

AGGREGATES;

1,4 DIPHENYL 1,2,3 TRIAZOLE; 1,4-DIPHENYL-1,2,3-TRIAZOLE; IMIDAZOLE DERIVATIVE; LIPOSOME; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTAL; MICELLE; PHASE TRANSITIONS; SELF-ASSEMBLY; TRIBLOCK POLYPHILES;

CLICK CHEMISTRY; LIQUID CRYSTALS; PHASE TRANSITIONS; SELF-ASSEMBLY; TRIBLOCK POLYPHILES;

CALORIMETRY, DIFFERENTIAL SCANNING; CLICK CHEMISTRY; IMIDAZOLES; MICELLES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; TRIAZOLES; UNILAMELLAR LIPOSOMES;

EID: 84887999830     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301538     Document Type: Article

References (111)

1. L. M. Greig, D. Philp, Chem. Soc. Rev. 2001, 30, 287-302
2. V. E. Campbell, J. R. Nitschke, Synlett 2008, 20, 3077-3090
3. P. A. Gale, Phil. Trans. R. Soc. Lond. A. 2000, 358, 431-453
4. B. A. Grzybowski, C. E. Wilmer, J. Kim, K. P. Browne, K. J. M. Bishop, Soft Matter 2009, 5, 1110-1128
5. X. C. Jiang, Q. H. Zeng, C. Y. Chen, A. B. Yu, J. Mater. Chem. 2011, 21, 16797-16805.
6. B. M. Rosen, C. J. Wilson, D. A. Wilson, M. Peterca, M. R. Imam, V. Percec, Chem. Rev. 2009, 109, 6275-6540.
7. C. Tschierske, Chem. Soc. Rev. 2007, 36, 1930-1970.
8. C.-A. Palma, M. Cecchini, P. Samori, Chem. Soc. Rev. 2012, 41, 3713-3730.
9. S. Kutsumizu, Isr. J. Chem. 2012, 52, 844-853.
10. S. T. Hyde, in Handbook of Applied Surface and Colloid Chemistry, (Ed. , K. Holmberg,), Wiley, 2001, pp. 299-232.
11. S. Diele, Curr. Opin. Colloid Interface Sci. 2002, 7, 333-342
12. M. Imperor-Clerc, Curr. Opin. Colloid Interface Sci. 2005, 9, 370-376.
13. X. Zeng, G. Ungar, M. Impéror-Clerc, Nat. Mater. 2005, 4, 562.
14. C. Tschierske, J. Mater. Chem. 2001, 11, 2647-2671
15. C. Tschierske, Ann. Rep. Progr. Chem. Sect. C. 2001, 97, 191-267.
16. J. Israelachvili, Intermolecular and surface forces, 3 rd ed. Academic Press, Burlington, MA, 2010
17. S. Hassan, W. Rowe, G. J. T. Tiddy, in Handbook of applied surface and colloid chemistry, Vol. 1 (Ed.:, K. Holmberg,), Wiley, Chichester, 2002, p 465.
18. K. Borisch, S. Diele, P. Göring, C. Tschierske, Chem. Commun. 1996, 237-238.
19. K. Borisch, S. Diele, P. Göring, H. Kresse, C. Tschierske, J. Mater. Chem. 1998, 8, 529-543
20. K. Borisch, S. Diele, P. Göring, H. Müller, C. Tschierske, Liq. Cryst. 1997, 22, 427-443
21. K. Borisch, S. Diele, P. Göring, H. Kresse, C. Tschierske, Angew. Chem. 1997, 109, 2188-2190
22. Angew. Chem. Int. Ed. Engl. 1997, 36, 2087-2089
23. K. Borisch, C. Tschierske, P. Göring, S. Diele, Chem. Commun. 1998, 2711-2712
24. K. Borisch, C. Tschierske, P. Göring, S. Diele, Langmuir 2000, 16, 6701-6708
25. P. Fuchs, C. Tschierske, K. Raith, K. Das, S. Diele, Angew. Chem. 2002, 114, 650-653
26. Angew. Chem. Int. Ed. 2002, 41, 628-631
27. X. H. Cheng, S. Diele, C. Tschierske, Angew. Chem. 2000, 112, 605-608
28. Angew. Chem. Int. Ed. 2000, 39, 592-595
29. X. H. Cheng, M. K. Das, S. Diele, C. Tschierske, Langmuir 2002, 18, 6521-6529.
30. S. D. Hudson, H.-T. Jung, V. Percec, W.-D. Cho, G. Johansson, G. Ungar, V. S. K. Balagurusamy, Science 1997, 278, 449-452
31. V. Percec, W.-D. Cho, P. E. Mosier, G. Ungar, D. J. P. Yeardley, J. Am. Chem. Soc. 1998, 120, 11061-11070
32. V. Percec, M. N. Holerca, S. Uchida, W.-D. Cho, G. Ungar, Y.-S. Lee, D. J. P. Yeardley, Chem. Eur. J. 2002, 8, 1106-1117
33. D. J. P. Yeardley, G. Ungar, V. Percec, M. N. Holerca, G. Johansson, J. Am. Chem. Soc. 2000, 122, 1684- 1689.
34. G. Ungar, X. Zeng, Soft Mater. 2005, 1, 95-106.
35. U. Beginn, S. Keinath, M. Möller, Liq. Cryst. 1997, 23, 35-41.
36. U. Beginn, L. Yan, S. N. Chvalun, M. A. Shcherbina, A. Bakirov, M. Möller, Liq. Cryst. 2008, 35, 1073-1093.
37. Y. Sagara, T. Kato, Angew. Chem. 2008, 120, 5253-5256
38. Angew. Chem. Int. Ed. 2008, 47, 5175-5178
39. T. Hatano, T. Kato, Tetrahedron 2008, 64, 8368-8380
40. S. Yazaki, Y. Kamikawa, M. Yoshio, A. Hamasaki, T. Mukai, H. Ohno, T. Kato, Chem. Lett. 2008, 37, 538-539
41. T. Hatano, T. Kato, Chem. Commun. 2006, 1277-1279.
42. B. K. Cho, A. Jain, S. M. Gruner, U. Wiesner, Science 2004, 305, 1598-1601
43. A. Kohlmeier, D. Janietz, S. Diele, Chem. Mater. 2006, 18, 1483-1489
44. M. Lehmann, M. Jahr, Chem. Mater. 2008, 20, 5453-5456
45. S. Coco, C. Cordovilla, B. Donnio, P. Espinet, M. J. Garcia-Casas, D. Guillon, Chem. Eur. J. 2008, 14, 3544-3552
46. S. Kohmoto, Y. Hara, K. Kishikawa, Tetrahedron Lett. 2010, 51, 1508-1511
47. T. J. Song, B.-K. Cho, Soft Matter 2012, 8, 3419-3428
48. J. Jiménez, A. Laguna, A. M. Molter, J. L. Serrano, J. Barbera, L. Oriol, Chem. Eur. J. 2011, 17, 1029-1039.
49. T. Noguchi, K. Kishikawa, S. Kohmoto, Liq. Cryst. 2008, 35, 1043-1050
50. X. L. Zhou, T. Narayanan, Q. Li, Liq. Cryst. 2007, 34, 1243-1248.
51. X. H. Cheng, X. Q. Bai, S. Jing, H. Ebert, M. Prehm, C. Tschierske, Chem. Eur. J. 2010, 16, 4588-4601
52. X. H. Cheng, F. W. Su, R. Huang, H. F. Gao, M. Prehm, C. Tschierske, Soft Matter 2012, 8, 2274-2285.
53. S. H. Seo, J. H. Park, G. N. Tew, J. Y. Chang, Tetrahedron Lett. 2007, 48, 6839-6844
54. J. H. Park, M. S. Kim, S. H. Seo, J. Y. Chang, Bull. Korean Chem. Soc. 2011, 32, 2193-2198.
55. M. Lee, B. K. Cho, H. Kim, W. C. Zin, Angew. Chem. 1998, 110, 661-663
56. Angew. Chem. Int. Ed. 1998, 37, 638-640
57. D. Kim, S. Jon, H.-K. Lee, K. Baek, N.-K. Oh, W.-C. Zin, K. Kim, Chem. Commun. 2005, 5509-5511
58. J.-K- Kim, M.-K. Hong, J.-H. Ahn, M. Lee, Angew. Chem. 2005, 117, 332-336
59. Angew. Chem. Int. Ed. 2005, 44, 328-332.
60. T. Yasuda, H. Ooi, J. Morita, Y. Akama, K. Minoura, M. Funahashi, T. Shimomura, T. Kato, Adv. Funct. Mater. 2009, 19, 411-419.
61. M. Ariyoshi, M. Sugibayashi-Kajita, A. Suzuki-Ichihara, T. Kato, T. Kamei, E. Itoh, K. Ohta, J. Porphyrins Phthalocyanines 2012, 16, 1114-1123
62. H. Mukai, M. Yokokawa, M. Ichihara, K. Hatsusaka, K. Ohta, J. Porphyrins Phthalocyanines 2010, 14, 188-197.
63. T. Kato, T. Matsuoka, M. Nishii, Y. Kamikawa, K. Kanie, T. Nishimura, E. Yashima, S. Ujiie, Angew. Chem. 2004, 116, 2003-2006
64. Angew. Chem. Int. Ed. 2004, 43, 1969-1972.
65. V. Percec, M. R. Imam, M. Peterca, D. A. Wilson, R. Graf, H. W. Spiess, V. S. K. Balagurusamy, P. A. Heiney, J. Am. Chem. Soc. 2009, 131, 7662-7667.
66. B. M. Rosen, D. A. Wilson, C. J. Wilson, M. Peterca, B. C. Won, C. Huang, L. R. Lipski, X. Zeng, G. Ungar, P. A. Heiney, V. Percec, J. Am. Chem. Soc. 2009, 131, 17500-17521
67. M. Peterca, M. R. Imam, P. Leowanawat, B. M. Rosen, D. A. Wilson, C. J. Wilson, X. Zeng, G. Ungar, P. A. Heiney, V. Percec, J. Am. Chem. Soc. 2010, 132, 11288-11305.
68. C. W. Tornøe, M. Meldal, Peptidotriazoles: Copper(I)-catalyzed 1,3-dipolar cycloadditions on solid-phase, Peptides 2001, Proc. Am. Pept. Symp, American Peptide Society and Kluwer Academic Publishers, San Diego, CA. 2001, pp 263-264
69. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064
70. V. V. Rostovtsev, L. G. Green, V. V. Fokin, B. K. Sharpless, Angew. Chem. 2002, 114, 2708-2711
71. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
72. M. Meldal, C. W. Tornøe, Chem. Rev. 2008, 108, 2952-3015
73. R. W. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128-1137.
74. A. C. Tome, R. C. Storr, T. L. Gilchrist, Science of Synthesis, vol. 13, Thieme, Stuttgart, 2004, pp. 415
75. V. P. Krivopalov, O. P. Russ Shkurko, Russ. Chem. Rev. 2005, 74, 339-379.
76. G. Nagarjuna, S. Yurt, K. G. Jadhav, D. Venkataraman, Macromolecules 2010, 43, 8045-8050.
77. G. Conte, R. Cristiano, F. Ely, H. Gallardo, Synth. Commun. 2006, 36, 951-958
78. A. A. Vieira, R. Cristiano, A. J. Bortoluzzi, H. Gallardo, J. Mol. Struct. 2008, 875, 364-371
79. G. Conte, F. Ely, H. Gallardo, Liq. Cryst. 2005, 32, 1213-1222
80. H. Gallardo, A. J. Bortoluzzi, D. M. P. D. Santos, Liq. Cryst. 2008, 35, 719-725
81. H. Gallardo, A. J. Bortoluzzi, G. Conte, Liq. Cryst. 2005, 32, 667-671.
82. E. Beltrán, J. L. Serrano, T. Sierra, R. Gimenez, Org. Lett. 2010, 12, 1404-1407
83. E. Beltrán, J. L. Serrano, T. Sierra, R. Gimenez, J. Mater. Chem. 2012, 22, 7797-7805
84. K. C. Majumdar, N. De, B. Roy, A. Bhaumik, Liq. Cryst. 2010, 37, 1459-1464
85. J.-W. Choi, M.-H. Ryu, E. Lee, B.-K. Cho, Chem. Eur. J. 2010, 16, 9006-9009.
86. N. Gimeno, R. Martin-Rapun, S. Rodrbox drawings light down and leftguez-Conde, J. L. Serrano, C. L. Folcia, M. A. Pericas, M. B. Ros, J. Mater. Chem. 2012, 22, 16791-16800.
87. V. Van Rheenen, D. Y. Cha, W. M. Hartley, Org. Synth. 1978, 58, 43-51.
88. P. Ziherl, R. D. Kamien, J. Phys. Chem. B. 2001, 105, 10147-10158
89. G. M. Grason, B. A. DiDonna, R. D. Kamien, Phys. Rev. Lett. 2003, 91, 058304.
90. A. Immirzi, B. Perini, Acta Crystallogr. Sect. A. 1997, 33, 216-218.
91. V. Percec, W. D. Cho, G. Ungar, D. J. P. Yeardley, J. Am. Chem. Soc. 2001, 123, 1302-1315.
92. J. Malthete, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171-187
93. H. T. Nguyen, C. Destrade, J. Malthete, Adv. Mater. 1997, 9, 375-388
94. X. W. Wang, C. M. Cho, W. Y. Say, A. Y. X. Tan, C. He, H. S. O. Chan, J. Xu, J. Mater. Chem. 2011, 21, 5248-5257
95. X. Zeng, L. Cseh" G. H. Mehl, G. Ungar, J. Mater. Chem. 2008, 18, 2953-2961.
96. B. M. Rosen, M. Peterca, C. Huang, X. Zeng, G. Ungar, V. Percec, Angew. Chem. 2011, 122, 7156-7159
97. Angew. Chem. Int. Ed. 2010, 49, 7002-7005.
98. S. Lecommandoux, H.-A. Klok, M. Sayar, S. I. Stupp, J. Polym. Sci. Part A 2003, 41, 3501-3518.
99. M. Sorai, K. Saito, Chem. Rec. 2003, 3, 29-39.
100. S. Buathong, D. Ung, T. J. Daou, C. Ulhaq-Bouillet, G. Pourroy, D. Guillon, L. Ivanova, I. Bernhardt, S. Begin-Colin, B. Donnio, J. Phys. Chem. C. 2009, 113, 12201-12212.
101. X. Zhu, B. Tartsch, U. Beginn, M. Möller, Chem. Eur. J. 2004, 10, 3871-3878.
102. J. H. Fuhrhop, T. Wang, Chem. Rev. 2004, 104, 2901-2937.
103. V. Luzzati, H. Mustacchi, A. Skoulios, Discuss. Faraday Soc. 1958, 25, 43-50.
104. X. Li, S. Kang, S. K. Lee, M. Tokita, J. Watanabe, Jpn. J. Appl. Phys. 2010, 49, 121701-121706
105. X. Li, M. Zhan, K. Wang, H. Zhou, Chem. Lett. 2011, 40, 820
106. S. Kang, M. Harada, X. Li, M. Tokita, J. Watanabe, Soft Matter 2012, 8, 1916-1922.
107. M. Peterca, V. Percec, P. Leowanawat, A. Bertin, J. Am. Chem. Soc. 2011, 133, 20507-20520.
108. V. Percec, M. R. Imam, T. K. Bera, V. S. K. Balagurusamy, M. Peterca, P. A. Heiney, Angew. Chem. 2005, 117, 4817-4823
109. Angew. Chem. Int. Ed. 2005, 44, 4739-4745.
110. I. Bury, B. Heinrich, C. Bourgogne, G. H. Mehl, D. Guillon, B. Donnio, New J. Chem. 2012, 36, 452-468.
111. H.-J. Kim, F. Liu, J.-H. Ryu, S.-K. Kang, X. Zeng, G. Ungar, J. K. Lee, W.-C. Zin, M. Lee, J. Am. Chem. Soc. 2012, 134, 13871-13880.