Evolution from lyotropic liquid crystal to helical fibrous organogel of an achiral fluorescent twin-tapered bi-1,3,4-oxadiazole derivative

Chemistry - A European Journal

Volumn 17, Issue 12, 2011, Pages 3512-3518

  Qu, Songnan ^a   Wang, Lijun ^a   Liu, Xingyuan ^a   Li, Min ^b  

^a CHANGCHUN INSTITUTE OF OPTICS   (China)

^b JILIN UNIVERSITY   (China)

Author keywords

helical structures; liquid crystals; organogels; oxadiazoles; self assembly

Indexed keywords

AGGREGATE FORMATION; DRIVING FORCES; HELICAL STRUCTURES; HIERARCHICAL SELF-ASSEMBLY; INTERMEDIATE LAYERS; LIQUID-CRYSTALLINE; LYOTROPIC LIQUID CRYSTAL; LYOTROPICS; NONUNIFORM; ORGANOGELS; OXADIAZOLE DERIVATIVES; OXADIAZOLES; SELF ASSEMBLY PROCESS; SUPRAMOLECULAR CHIRALITY;

CONCENTRATION (PROCESS); CRYSTALS; FLUORESCENCE; LIQUID CRYSTALS; STEREOCHEMISTRY;

SELF ASSEMBLY;

(2,2 BIS(3,4,5 TRIOCTANOXYPHENYL) BI 1,3,4 OXADIAZOLE); (2,2-BIS(3,4,5-TRIOCTANOXYPHENYL)-BI-1,3,4-OXADIAZOLE); OXADIAZOLE DERIVATIVE; SOLVENT;

ARTICLE; ATTENTION; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; LIQUID CRYSTAL; STEREOISOMERISM;

ATTENTION; CIRCULAR DICHROISM; LIQUID CRYSTALS; MOLECULAR STRUCTURE; OXADIAZOLES; SOLVENTS; STEREOISOMERISM;

EID: 79952410046     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003156     Document Type: Article

References (100)

1. N. Berova, K. Nakanishi, R. W. Woody, (Eds.), Circular Dichroism: Principles and Applications, 2 nd ed., Wiley-VCH, New York, 2000
2. D. Clines, (Ed.), The Physical Origin of Homochirality in Life, AIP Press, Woodbury, New York, 1996
3. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, Wiley-VCH, Weinheim, 1995
4. A. Guijarro, M. Yus, The Origin of Chirality in the Molecules of Life, RSC, Cambridge, 2009
5. E. L. Eliel, S. H. Wilen, L. N. Mander, Stereochemistry of Organic Compounds, Wiley, New York, 1994
6. H. G. Kuball, T. Höfer, Chirality 2000, 12, 278
7. L. Pérez-García, D. B. Amabilino, Chem. Soc. Rev. 2002, 31, 342
8. M. Quack, Angew. Chem. 2002, 114, 4812
9. Angew. Chem. Int. Ed. 2002, 41, 4618
10. R. Lemieux, Acc. Chem. Res. 2001, 34, 845
11. R. Holzwarth, R. Bartsch, Z. Cherkaoui, G. Solladie, Chem. Eur. J. 2004, 10, 3931
12. A. Brizard, R. Oda, I. Huc, Top. Curr. Chem. 2005, 256, 167.
13. C. C. Lee, C. Grenier, E. W. Meijer, A. P. H. J. Schenning, Chem. Soc. Rev. 2009, 38, 671
14. F. Vera, J. L. Serrano, T. Sierra, Chem. Soc. Rev. 2009, 38, 781
15. Z. Chen, A. Lohr, C. R. S. Möller, F. Würthner, Chem. Soc. Rev. 2009, 38, 564
16. J. H. Ryu, D. J. Hong, M. Lee, Chem. Commun. 2008, 1043
17. H. Frauenrath, E. Jahnke, Chem. Eur. J. 2008, 14, 2942
18. G. A. Hembury, V. V. Borovkov, Y. Inoue, Chem. Rev. 2008, 108, 1
19. S. Yagai, H. Aonuma, Y. Kikkawa, S. Kubota, T. Karatsu, A. Kitamura, S. Mahesh, A. Ajayaghosh, Chem. Eur. J. 2010, 16, 8652
20. V. K. Praveen, S. S. Babu, C. Vijayakumar, R. Varghese, A. Ajayaghosh, Bull. Chem. Soc. Jpn. 2008, 81, 1196.
21. K. Tang, M. M. Green, K. S. Cheon, J. V. Selinger, B. A. Garetz, J. Am. Chem. Soc. 2003, 125, 7313
22. J. vanGestel, A. R. A. Palmans, B. Titulaer, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2005, 127, 5490
23. M. M. J. Smulders, A. P. H. J. Schenning, E. W. Meijer, J. Am. Chem. Soc. 2008, 130, 606
24. Y. Li, T. Wang, M. Liu, Soft Matter 2007, 3, 1312
25. T. Miyagawa, M. Yamamoto, R. Muraki, H. Onouchi, E. Yashima, J. Am. Chem. Soc. 2007, 129, 3676
26. K. Morino, N. Watase, K. Maeda, E. Yashima, Chem. Eur. J. 2004, 10, 4703
27. D. Ogata, T. Shikata, K. Hanabusa, J. Phys. Chem. B 2004, 108, 15503
28. M. Waki, H. Abe, M. Inouye, Angew. Chem. 2007, 119, 3119
29. Angew. Chem. Int. Ed. 2007, 46, 3059
30. R. M. Meudtner, S. Hecht, Angew. Chem. 2008, 120, 5004
31. Angew. Chem. Int. Ed. 2008, 47, 4926
32. W. Cai, G. T. Wang, P. Du, R. X. Wang, X. K. Jiang, Z. T. Li, J. Am. Chem. Soc. 2008, 130, 13450.
33. E. D. Sone, E. R. Zubrarev, S. I. Stupp, Angew. Chem. 2002, 114, 1781
34. Angew. Chem. Int. Ed. 2002, 41, 1705
35. U. Siemeling, I. Scheppelmann, B. Neumann, A. Stammel, H. G. Stammler, J. Frelek, Chem. Commun. 2003, 2236
36. K. Köhler, G. Föester, A. Hauster, B. Dobner, U. F. Heiser, F. Ziethe, W. Richter, F. Steiniger, M. Drechsler, H. Stettin, A. Blume, J. Am. Chem. Soc. 2004, 126, 16804
37. G. Pelzl, S. Diele, W. Weissflog, Adv. Mater. 1999, 11, 707
38. K. U. Jeong, S. Jin, J. J. Ge, B. S. Knapp, M. J. Graham, J. Ruan, M. Guo, H. Xiong, F. W. Harris, S. Z. D. Cheng, Chem. Mater. 2005, 17, 2852
39. U. Jeong, B. S. Knapp, J. J. Ge, S. Jin, M. J. Graham, F. W. Harris, S. Z. D. Cheng, Chem. Mater. 2006, 18, 680
40. Y. Qiu, P. Chen, P. Guo, Y. Li, M. Liu, Adv. Mater. 2008, 20, 2908
41. Y. Qiu, P. Chen, M. Liu, J. Am. Chem. Soc. 2010, 132, 9644
42. D. M. Walba, E. Korblova, C. C. Huang, R. Shao, M. Nakata, N. A. Clark, J. Am. Chem. Soc. 2006, 128, 5318
43. O. Arteaga, C. Escudero, G. Oncins, Z. El-Hachemi, J. Llorens, J. Crusats, A. Canillas, J. M. Ribõ, Chem. Asian J. 2009, 4, 1687
44. Z. El-Hachemi, C. Escudero, O. Arteaga, A. Canillas, J. Crusats, G. Mancini, R. Purrello, A. Sorrenti, Al. D'′Urso, J. M. Ribõ, Chirality 2009, 21, 408
45. R. Lauceri, A. Raudino, L. M. Scolaro, N. Micali, R. Purrello, J. Am. Chem. Soc. 2002, 124, 894.
46. T. Sekine, T. Niori, J. Watanabe, T. Furukawa, S. W. Choi, H. Takezoe, J. Mater. Chem. 1997, 7, 1307
47. D. R. Link, G. Natale, R. Shao, J. E. Maclennan, N. A. Clark, E. Körblova, D. M. Walba, Science 1997, 278, 1924
48. D. A. Coleman, J. Fernsler, N. Chattham, M. Nakata, Y. Takanishi, E. Körblova, D. R. Link, R.-F. Shao, W. G. Jang, J. E. Maclennan, O. Mondainn-Monval, C. Boyer, W. Weissflog, G. Pelzl, L.-C. Chien, J. Zasadzinski, J. Watanabe, D. M. Walba, H. Takezoe, N. A. Clark, Science 2003, 301, 1204
49. H. N. ShreenivasaMurthy, B. K. Sadashiva, J. Mater. Chem. 2003, 13, 2863
50. R. AmaranathaReddy, M. W. Schröder, M. Bodyagin, H. Kresse, S. Diele, G. Pelzl, W. Weissflog, Angew. Chem. 2005, 117, 784
51. Angew. Chem. Int. Ed. 2005, 44, 774
52. R. A. Reddy, C. Tschierske, J. Mater. Chem. 2006, 16, 907
53. V. Görtz, J. W. Goodby, Chem. Commun. 2005, 3262
54. J. Thisayukta, Y. Nakayama, S. Kawauchi, H. Takezoe, J. Watanabe, J. Am. Chem. Soc. 2000, 122, 7441
55. J. Etxebarria, M. B. Ros, J. Mater. Chem. 2008, 18, 2919.
56. J. M. Ribõ, J. Crusats, F. Sagués, J. Claret, R. Rubires, Science 2001, 292, 2063
57. J. Crusats, J. Claret, I. Díez-Pérez, Z. El-Hachemi, H. García-Ortega, R. Rubires, F. Sagués, J. M. Ribõ, Chem. Commun. 2003, 1588
58. J. Crusats, Z. El-Hachemi, J. M. Ribõ, Chem. Soc. Rev. 2010, 39, 569.
59. J. Yuan, M. Liu, J. Am. Chem. Soc. 2003, 125, 5051
60. L. Zhang, Q. Lu, M. H. Liu, J. Phys. Chem. B 2003, 107, 2565
61. X. Huang, C. Li, S. Jiang, X. Wang, B. Zhang, M. Liu, J. Am. Chem. Soc. 2004, 126, 1322
62. P. Guo, M. Liu, Langmuir 2005, 21, 3410.
63. C. Bao, R. Lu, M. Jin, P. Xue, C. Tan, T. Xu, G. Liu, Y. Zhao, Chem. Eur. J. 2006, 12, 3287.
64. L. L. Cheng, Y. Y. Luk, C. J. Murphy, B. A. Israel, N. L. Abbott, Biomaterials 2005, 26, 7173
65. S. V. Shiyanovskii, T. Schneider, I. I. Smalyukh, T. Ishikawa, G. D. Niehaus, K. J. Doane, C. J. Woolverton, O. D. Lavrentovitch, Phys. Rev. E 2005, 71, 020702
66. W. C. Pomerantz, N. L. Abbott, S. H. Gellman, J. Am. Chem. Soc. 2006, 128, 8730
67. I. W. Hamley, M. J. Krysmann, V. Castelletto, L. Noirez, Adv. Mater. 2008, 20, 4394.
68. N. M. Sangeetha, U. Maitra, Chem. Soc. Rev. 2005, 34, 821
69. M. George, R. G. Weiss, Acc. Chem. Res. 2006, 39, 489
70. A. Ajayaghosh, V. K. Praveen, Acc. Chem. Res. 2007, 40, 644
71. P. Dastidar, Chem. Soc. Rev. 2008, 37, 2699.
72. C. Vijayakumar, V. K. Praveen, A. Ajayaghosh, Adv. Mater. 2009, 21, 2059
73. S. S. Babu, V. K. Praveen, S. Prasanthkumar, A. Ajayaghosh, Chem. Eur. J. 2008, 14, 9577
74. A. Ajayaghosh, V. K. Praveen, C. Vijayakumar, S. J. George, Angew. Chem. 2007, 119, 6376
75. Angew. Chem. Int. Ed. 2007, 46, 6260
76. A. Ajayaghosh, V. K. Praveen, S. Srinivasan, R. Varghese, Adv. Mater. 2007, 19, 411
77. A. Ajayaghosh, R. Varghese, V. K. Praveen, S. Mahesh, Angew. Chem. 2006, 118, 3339
78. Angew. Chem. Int. Ed. 2006, 45, 3261
79. V. K. Praveen, S. J. George, R. Varghese, C. Vijayakumar, A. Ajayaghosh, J. Am. Chem. Soc. 2006, 128, 7542
80. A. Ajayaghosh, C. Vijayakumar, V. K. Praveen, S. S. Babu, R. Varghese, J. Am. Chem. Soc. 2006, 128, 7174
81. Y. Hirai, S. S. Babu, V. K. Praveen, T. Yasuda, A. Ajayaghosh, T. Kato, Adv. Mater. 2009, 21, 4029
82. J. W. Chung, S. J. Yoon, S. J. Lim, B. K. An, S. Y. Park, Angew. Chem. 2009, 121, 7164
83. Angew. Chem. Int. Ed. 2009, 48, 7030
84. B. K. An, D. S. Lee, J. S. Lee, Y. S. Park, H. S. Song, S. Y. Park, J. Am. Chem. Soc. 2004, 126, 10232
85. K. Sugiyasu, N. Fujita, S. Shinkai, Angew. Chem. 2004, 116, 1249
86. Angew. Chem. Int. Ed. 2004, 43, 1229
87. P. C. Xue, R. Lu, G. J. Chen, Y. Zhang, H. Nomoto, M. Takafuji, H. Ihara, Chem. Eur. J. 2007, 13, 8231
88. Q. Chen, D. Zhang, G. Zhang, X. Yang, Y. Feng, Q. Fan, D. Zhu, Adv. Funct. Mater. 2010, 20, 3244.
89. R. Ziessel, G. Pickaert, F. Camerel, B. Donnio, D. Guillon, M. Cesario, T. Prange, J. Am. Chem. Soc. 2004, 126, 12403
90. G. C. Kuang, Y. Ji, X. R. Jia, Y. Li, E. Q. Chen, Y. Wei, Chem. Mater. 2008, 20, 4173.
91. S. Qu, M. Li, Tetrahedron 2007, 63, 12429
92. S. Qu, L. Zhao, Z. Xiu, M. Li, Langmuir 2009, 25, 1713
93. S. Qu, X. Chen, X. Shao, F. Li, H. Zhang, H. Wang, P. Zhang, Z. Yu, K. Wu, Y. Wang, M. Li, J. Mater. Chem. 2008, 18, 3954
94. P. Zhang, S. Qu, H. Wang, B. Bai, M. Li, Liquid Crystals 2008, 35, 389.
95. J. vanEsch, S. D. Feyter, R. M. Kellogg, F. D. Schryver, B. L. Feringa, Chem. Eur. J. 1997, 3, 1238
96. S. Qu, H. Wang, Z. Yu, B. Bai, M. Li, New J. Chem. 2008, 32, 2023.
97. R. B. Martin, Chem. Rev. 1996, 96, 3043
98. F. Huang, H. W. Gibson, J. Am. Chem. Soc. 2004, 126, 14738
99. S. Qu, F. Li, H. Wang, B. Bai, C. Xu, L. Zhao, B. Long, M. Li, Chem. Mater. 2007, 19, 4839
100. S. Qu, M. Li, Tetrahedron 2008, 64, 10890.