Self-assembly of carbazole-containing gelators: alignment of the chromophore in fibrous aggregates

Tetrahedron

Volumn 63, Issue 31, 2007, Pages 7358-7365

  Yabuuchi, Kazuhiro ^a   Tochigi, Yusuke ^a   Mizoshita, Norihiro ^a   Hanabusa, Kenji ^b   Kato, Takashi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

Carbazole; Liquid crystal; Organogel; Self assembled fiber

Indexed keywords

CARBAZOLE DERIVATIVE; ISOLEUCINE; ORGANIC SOLVENT;

ANISOTROPY; ARTICLE; CHROMATOPHORE; DISSOCIATION; FIBER; GELATION; HYDROGEN BOND; LIQUID CRYSTAL; PRIORITY JOURNAL; SPECTROSCOPY;

EID: 34250673590     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.121     Document Type: Article

References (83)

1. Lehn J.-M. Science 295 (2002) 2400-2403
2. Ciferri A. Supramolecular Polymers. 2nd ed. (2005), Marcel Dekker, New York, NY
3. Reinhoudt D.N., and Crego-Calama M. Science 295 (2002) 2403-2407
4. Kato T. Science 295 (2002) 2414-2418
5. Kato T., Mizoshita N., and Kishimoto K. Angew. Chem., Int. Ed. 45 (2006) 38-68
6. Hoeben F.J.M., Jonkheijm P., Meijer E.W., and Schenning A.P.H.J. Chem. Rev. 105 (2005) 1491-1546
7. Ikkala O., and ten Brinke G. Chem. Commun. (2004) 2131-2137
8. Abdallah D.J., and Weiss R.G. Adv. Mater. 12 (2000) 1237-1247
9. van Esch J.H., and Feringa B.L. Angew. Chem., Int. Ed. 39 (2000) 2263-2266
10. Shinkai S., and Murata K. J. Mater. Chem. 8 (1998) 485-495
11. In: Weiss R.G., and Terech P. (Eds). Molecular Gels (2005), Kluwer Academic, Amsterdam
12. Liu X.Y. Top. Curr. Chem. 256 (2005) 1-37
13. Žinic M., Vögtle F., and Fages F. Top. Curr. Chem. 256 (2005) 39-76
14. Fages F., Vögtle F., and Žinic M. Top. Curr. Chem. 256 (2005) 77-131
15. Araki K., and Yoshikawa I. Top. Curr. Chem. 256 (2005) 133-165
16. Brizard A., Oda R., and Huc I. Top. Curr. Chem. 256 (2005) 167-218
17. Kato T., Mizoshita N., Moriyama M., and Kitamura T. Top. Curr. Chem. 256 (2005) 219-236
18. Hirst A.R., and Smith D.K. Top. Curr. Chem. 256 (2005) 237-273
19. Estroff L.A., and Hamilton A.D. Chem. Rev. 104 (2004) 1201-1218
20. Sangeetha N.M., and Maitra U. Chem. Soc. Rev. 34 (2005) 821-836
21. Hanabusa K., Yamada M., Kimura M., and Shirai H. Angew. Chem., Int. Ed. 35 (1996) 1949-1951
22. Hafkamp R.J.H., Feiters M.C., and Nolte R.J.M. J. Org. Chem. 64 (1999) 412-426
23. Yoza K., Amanokura N., Ono Y., Akao T., Shinmori H., Takeuchi M., Shinkai S., and Reinhoudt D.N. Chem.-Eur. J. 5 (1999) 2722-2729
24. van Esch J., Schoonbeek F., de Loos M., Kooijman H., Spek A.L., Kellogg R.M., and Feringa B.L. Chem.-Eur. J. 5 (1999) 937-950
25. Brotin T., Utermöhlen R., Fages F., Bouas-Laurent H., and Desvergne J.-P. J. Chem. Soc., Chem. Commun. (1991) 416-418
26. Estroff L.A., and Hamilton A.D. Angew. Chem., Int. Ed. 39 (2000) 3447-3450
27. Yabuuchi K., Marfo-Owusu E., and Kato T. Org. Biomol. Chem. 1 (2003) 3464-3469
28. Dykes G.M., and Smith D.K. Tetrahedron 59 (2003) 3999-4009
29. Trivedi D.R., Ballabh A., Dastidar P., and Ganguly B. Chem.-Eur. J. 10 (2004) 5311-5322
30. Inoue D., Suzuki M., Shirai H., and Hanabusa K. Bull. Chem. Soc. Jpn. 78 (2005) 721-726
31. Suzuki M., Sato T., Kurose A., Shirai H., and Hanabusa K. Tetrahedron Lett. 46 (2005) 2741-2745
32. Makarević J., Jokić M., Perić B., Tomišić V., Kojić-Prodić B., and Žinić M. Chem.-Eur. J. 7 (2001) 3328-3341
33. Schoonbeek F.S., van Esch J., Wegewijs B., Rep D.B.A., Klapwijk T.M., Kellogg R.M., and Feringa B.L. Angew. Chem., Int. Ed. 38 (1999) 1393-1397
34. Liu P., Shirota Y., and Osada Y. Polym. Adv. Technol. 11 (2000) 512-517
35. Ishi-i T., Jung J.H., and Shinkai S. J. Mater. Chem. 10 (2000) 2238-2240
36. Kimura M., Kitamura T., Muto T., Hanabusa K., Shirai H., and Kobayashi N. Chem. Lett. (2000) 1088-1089
37. Jørgensen M., and Bechgaard K. J. Org. Chem. 59 (1994) 5877-5882
38. Kitahara T., Shirakawa M., Kawano S., Beginn U., Fujita N., and Shinkai S. J. Am. Chem. Soc. 127 (2005) 14980-14981
39. Kitamura T., Nakaso S., Mizoshita N., Tochigi Y., Shimomura T., Moriyama M., Ito K., and Kato T. J. Am. Chem. Soc. 127 (2005) 14769-14775
40. Tamaoki N., Shimada S., Okada Y., Belaissaoui A., Kruz G., Yase K., and Matsuda H. Langmuir 16 (2000) 7545-7547
41. Masuda M., Hanada T., Okada Y., Yase K., and Shimizu T. Macromolecules 33 (2000) 9233-9238
42. Su L., Bao C., Lu R., Chen Y., Xu T., Song D., Tan C., Shi T., and Zhao Y. Org. Biomol. Chem. 4 (2006) 2591-2594
43. Li X.-Q., Stepanenko V., Chen Z., Prins P., Siebbelesb L.D.A., and Würthner F. Chem. Commun. (2006) 3871-3873
44. George S.J., Ajayaghosh A., Jonkheijm P., Schenning A.P.H.J., and Meijer E.W. Angew. Chem., Int. Ed. 43 (2004) 3422-3425
45. Kamikawa Y., and Kato T. Langmuir 23 (2007) 274-278
46. Murata K., Aoki M., Suzuki T., Harada T., Kawabata H., Komori T., Ohseto F., Ueda K., and Shinkai S. J. Am. Chem. Soc. 116 (1994) 6664-6676
47. de Loos M., van Esch J., Kellogg R.M., and Feringa B.L. Angew. Chem., Int. Ed. 40 (2001) 613-616
48. Moriyama M., Mizoshita N., Yokota T., Kishimoto K., and Kato T. Adv. Mater. 15 (2003) 1335-1338
49. Moriyama M., Mizoshita N., and Kato T. Bull. Chem. Soc. Jpn. 79 (2006) 962-964
50. Moriyama M., Mizoshita N., and Kato T. Polym. J. 36 (2004) 661-664
51. Mamiya J., Kanie K., Hiyama T., Ikeda T., and Kato T. Chem. Commun. (2002) 1870-1871
52. Sugiyasu K., Fujita N., Takeuchi M., Yamada S., and Shinkai S. Org. Biomol. Chem. 1 (2003) 895-899
53. Zhao Y., and Tong X. Adv. Mater. 15 (2003) 1431-1435
54. Deindörfer P., Eremin A., Stannarius R., Davisa R., and Zentel R. Soft Matter 2 (2006) 693-698
55. Kato T., Kutsuna T., Hanabusa K., and Ukon M. Adv. Mater. 10 (1998) 606-608
56. Yabuuchi K., Rowan A.E., Nolte R.J.M., and Kato T. Chem. Mater. 12 (2000) 440-443
57. Mizoshita N., Hanabusa K., and Kato T. Adv. Mater. 11 (1999) 392-394
58. Mizoshita N., Hanabusa K., and Kato T. Adv. Funct. Mater. 13 (2003) 313-317
59. Mizoshita N., Suzuki Y., Hanabusa K., and Kato T. Adv. Mater. 17 (2005) 692-696
60. Mizoshita N., and Kato T. Adv. Funct. Mater. 16 (2006) 2218-2224
61. Mizoshita N., Kutsuna T., Hanabusa K., and Kato T. Chem. Commun. (1999) 781-782
62. Kato T., Kutsuna T., Yabuuchi K., and Mizoshita N. Langmuir 18 (2002) 7086-7088
63. Mizoshita N., Monobe H., Inoue M., Ukon M., Watanabe T., Shimizu Y., Hanabusa K., and Kato T. Chem. Commun. (2002) 428-429
64. Kubo W., Kitamura T., Hanabusa K., Wada Y., and Yanagida S. Chem. Commun. (2002) 374-375
65. Placin F., Desvergne J.-P., and Lassègues J.-C. Chem. Mater. 13 (2001) 117-121
66. Hanabusa K., Hiratsuka K., Kimura M., and Shirai H. Chem. Mater. 11 (1999) 649-655
67. Hanabusa K., Fukui H., Suzuki M., and Shirai H. Langmuir 21 (2005) 10383-10390
68. Ikeda A., Sonoda K., Ayabe M., Tamaru S., Nakashima T., Kimizuka N., and Shinkai S. Chem. Lett. (2001) 1154-1155
69. van Bommel K.J.C., Friggeri A., and Shinkai S. Angew. Chem., Int. Ed. 42 (2003) 980-999
70. Kobayashi S., Hanabusa K., Hamasaki N., Kimura M., Shirai H., and Shinkai S. Chem. Mater. 12 (2000) 1523-1525
71. Yang Y., Fukui H., Suzuki M., Shirai H., and Hanabusa K. Bull. Chem. Soc. Jpn. 78 (2005) 2069-2074
72. Adam D., Schuhmacher P., Simmerer J., Häussling L., Siemensmeyer K., Etzbach K.H., Ringsdorf H., and Haarer D. Nature 371 (1994) 141-143
73. Hulvat J.F., and Stupp S.I. Angew. Chem., Int. Ed. 42 (2003) 778-781
74. Bushey M.L., Nguyen T.-Q., and Nuckolls C. J. Am. Chem. Soc. 125 (2003) 8264-8269
75. Li L., Beniash E., Zubarev E.R., Xiang W., Rabatic B.M., Zhang G., and Stupp S.I. Nature Mater. 2 (2003) 689-694
76. Beginn U., Zipp G., and Möller M. Adv. Mater. 12 (2000) 510-513
77. Yoshio M., Mukai T., Ohno H., and Kato T. J. Am. Chem. Soc. 126 (2004) 994-995
78. Hogel H. J. Phys. Chem. 69 (1965) 755-766
79. Pai D.M. J. Chem. Phys. 52 (1970) 2285-2291
80. Dutta A.K. Langmuir 12 (1996) 5909-5914
81. Johnson G.E. J. Chem. Phys. 62 (1975) 4697-4709
82. Itaya A., Okamoto K., and Kusabayashi S. Bull. Chem. Soc. Jpn. 49 (1976) 2082-2088
83. Li X., Mintz E.A., Bu X.R., Zehnder O., Bosshard C., and Günter P. Tetrahedron 56 (2000) 5785-5791