Spectroscopic properties and gelling ability of a set of rod-like 2,3-disubstituted anthracenes

New Journal of Chemistry

Volumn 28, Issue 2, 2004, Pages 234-243

  Desvergne, Jean Pierre ^a   Brotin, Thierry ^a   Meerschaut, Danny ^a   Clavier, Gilles ^a   Placin, Frédéric ^a   Pozzo, Jean Luc ^a   Bouas Laurent, Henri ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIDECYLOXYANTHRACENE; 2,3 DIOXYDIMETHYLENEANTHRACENE; 2,3 DIOXYTRIMETHYLENEANTHRACENE; ACETONITRILE; ALCOHOL; ANTHRACENE DERIVATIVE; CYCLOHEXANE DERIVATIVE; GELLING AGENT; METHANOL; METHYLCYCLOHEXANE; PROPANOL; UNCLASSIFIED DRUG;

ARTICLE; FLUORESCENCE; GEL; MELTING POINT; PARAMETER; PHASE TRANSITION; PRIORITY JOURNAL; SCREENING; SOLID STATE; TEMPERATURE DEPENDENCE; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 1542299115     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b306961c     Document Type: Article

References (93)

1. Reversible Polymeric Gels and Related Systems, ed. P. S. Russo, ACS Symposium Series 350, American Chemical Society, Washington, D.C., 1987.
2. Physical Networks, Polymers and Gels, eds. W. Buchard and S. B. Ross-Murphy, Elsevier Applied Science, London, 1990.
3. Food Polymers, Gels and Colloids, ed. E. Dickinson The Royal Society of Chemistry, Cambridge, UK, 1991.
4. J. M. Guenet, Thermoreversible Gelation of Polymers and Biopolymers, Academic Press, London, 1992.
5. J. H. Fuhrhop and W. Helfrich, Chem. Rev., 1993, 93, 1565.
6. K. te Nijenhuis, Thermoreversible Networks, Springer-Verlag, Berlin, 1997.
7. (a) T. Tanaka, C. Wang, V. Pande, A. Y. Grosberg, A. English, S. Masamune, H. Gold, R. Levy and K. King, Faraday Discuss., 1996, 102, 201;
8. (b) "Physikalische Chemie der Gele und Netzwerke", guest eds. H. Hoffman, H. Rehage and W. Oppermann, Ber. Bunsenges Phys. Chem., 1998, 102, 1523-1717.
9. (a) M. Jacoby, Chem. Eng. News, 1997, 75(43), 10;
10. (b) R. Dagani, Chem. Eng. News, 1997, 75(23), 26.
11. (a) P. Terech and R. G. Weiss, Chem. Rev., 1997, 97, 3133;
12. (b) P. Terech, Ber. Bunsenges. Phys. Chem., 1998, 102, 1630.
13. W. Gu, L. Lu, G. B. Chapman and R. G. Weiss, Chem. Commun., 1997, 543.
14. J. van Esch, S. de Feyter, R. M. Kellog, F. de Schryver and B. L. Feringa, Chem.-Eur. J., 1997, 3, 1238.
15. R. J. H. Hafkamp, B. P. A. Kokke, I. M. Danke, H. P. M. Geurts, A. E. Rowan, M. C. Feiters and R. J. M. Nolte, Chem. Commun., 1997, 545.
16. J. E. Sohna-Sohna and F. Fages, Chem. Commun., 1997, 327.
17. M. de Loos, J. van Esch, I. Stokroos, R. M. Kellogg and B. L. Feringa, J. Am. Chem. Soc., 1997, 119, 12 675.
18. C. M. Garner, P. Terech, J. J. Allegraud, B. Mistrot, P. Nguyen, A. de Geyer and D. Rivera, J. Chem. Soc., Faraday Trans., 1998, 94, 2173.
19. (a) S. Yamasaki and H. Tsutsumi, Bull. Chem. Soc. Jpn., 1996, 69, 561;
20. (b) M. Watase and H. Itagaki, Bull. Chem. Soc. Jpn., 1998, 71, 1457;
21. (c) M. Watase, Y. Nakatani and H. Itagaki, J. Phys. Chem. B, 1999, 103, 2366.
22. K. Inoue, Y. Ono, Y. Kanekiyo, T. Ishi-i, K. Yoshihara and S. Shinkai, Tetrahedron Lett., 1998, 39, 2981.
23. (a) R. Oda, I. Huc and S. J. Candau, Angew. Chem., Int. Ed., 1998, 37, 2689;
24. (b) R. Oda, I. Huc, M. Schmutz, S. J. Candau and F. C. Macintosh, Nature (London), 1999, 399, 566.
25. Y.-C. Lin and R. G. Weiss, Macromolecules, 1987, 20, 414.
26. Y.-C. Lin, B. Kachar and R. G. Weiss, J. Am. Chem. Soc., 1989, 111, 5542.
27. Y.-C. Lin and R. G. Weiss, Liq. Cryst., 1989, 4, 367.
28. I. Furman and R. G. Weiss, Langmuir, 1993, 9, 2084.
29. R. Mukkamala and R. G. Weiss, J. Chem. Soc. Chem. Commun., 1995, 375.
30. P. Terech, I. Furman and R. G. Weiss, J. Phys. Chem., 1995, 99, 9558.
31. P. Terech, E. Ostuni and R. G. Weiss, J. Phys. Chem., 1996, 100, 3759.
32. E. Ostuni, P. Kamaras and R. G. Weiss, Angew. Chem., Int. Ed. Engl., 1996, 35, 1324.
33. (a) D. J. Abdallah and R. G. Weiss, Langmuir, 2000, 16, 352;
34. (b) D. J. Abdallah, S. A. Sirchio and R. G. Weiss, Langmuir, 2000, 16, 7558;
35. (c) A. Ballabh, D. R. Trivedi and P. Dastidar, Chem. Mater., 2003, 15, 2136.
36. T. Brotin, R. Utermöhlen, F. Fages, H. Bouas-Laurent and J.-P. Desvergne, J. Chem. Soc., Chem. Commun., 1991, 416.
37. (a) P. Terech, J.-P. Desvergne and H. Bouas-Laurent, J. Colloid Interface Sci., 1995, 174, 258;
38. (b) P. Terech, I. Furman, R. G. Weiss, H. Bouas-Laurent, J.-P. Desvergne and R. Ramasseul, Faraday Discuss., 1996, 101, 345.
39. F. Placin, J.-P. Desvergne and F. Cansell, J. Mater. Chem., 2000, 10, 2147.
40. F. Placin, J.-P. Desvergne and J.-C. Lassègues, Chem. Mater., 2001, 13, 117.
41. (a) G. M. Clavier, J.-L. Pozzo, H. Bouas-Laurent, C. Liere, C. Roux and C. Sanchez, J. Mater. Chem., 2000, 10, 1725;
42. (b) M. Llusar, L. Pidol, C. Roux, J.-L. Pozzo and C. Sanchez, Chem. Mater., 2002, 14, 5124.
43. T. Kato, T. Kutsuna, K. Yabuuchi and N. Mizoshita, Langmuir, 2002, 18, 7086.
44. (a) K. Hanabusa, R. Tanaka, M. Suzuki, M. Kimura and S. Shirai, Adv. Mater., 1997, 8, 740;
45. (b) Y. Hishikawa, K. Sada, R. Watanabe, M. Miyata and K. Hanabusa, Chem. Lett., 1998, 795.
46. (a) S. Shinkai and K. Murata, J. Mater. Chem., 1998, 8, 485;
47. (b) K. Yoza, Y. Ono, K. Yoshihara, T. Akao, H. Shinmori, M. Takeuchi, S. Shinkai and D. N. Reinhoudt, Chem. Commun., 1998, 907;
48. (c) O. Gronwald and S. Shinkai, Chem.-Eur. J., 2001, 7, 4328;
49. (d) H. Kobayashi, A. Friggeri, K. Koumoto, M. Amaike, S. Shinkai and D. N. Reinhoudt, Org. Lett., 2002, 4, 1423 and references therein;
50. (e) O. Gronwald, E. Snip and S. Shinkai, Curr. Opin. Colloid Interface Sci., 2002, 7, 148. The lowest concentrations reported for methyl-4,6-O-/para- nitrobenzylidene-α-D-galactopyranoside and methyl-4,6-O-α-D- mannopyranoside in alkanes were found to be 0.9-2.5 mM.
51. (a) U. Maitra, P. V. Kumar, N. Chandra, L. J. D'Souza, M. D. Prasanna and A. R. Raju, Chem. Commun., 1999, 595;
52. (b) U. Maitra, P. V. Kumar, N. M. Sangeetha, P. Babu and A. R. Raju, Tetrahedron: Asymmetry, 2001, 12, 477.
53. (a) J. van Esch, F. Schoonbeek, M. De Loos, H. Kooijman, A. L. Spek, R. M. Kellogg and B. L. Feringa, Chem.-Eur. J., 1999, 5, 937;
54. (b) J. van Esch, F. Schoonbeek, M. De Loos, H. Kooijman, A. L. Spek, R. M. Kellogg and B. L. Feringa, Chem.-Eur. J., 1999, 5, 6445;
55. (c) L. N. Lucas, J. van Esch, R. M. Kellogg and B. L. Feringa, Chem. Commun., 2001, 759.
56. G. Clavier, M. Mistry, F. Fages and J. L. Pozzo, Tetrahedron Lett., 1999, 40, 9021.
57. H. Ihara, M. Yoshitake, M. Takafuji, T. Yamada, T. Sagawa, C. Hirayama and H. Hachisako, Liq. Cryst., 1999, 26, 1021.
58. L. A. Cuccia, J. M. Lehn, J. C. Homo and M. Schmutz, Angew. Chem., Int. Ed., 2000, 39, 233.
59. (a) L. D. Lu, T. M. Cocker, R. E. Bachman and R. G. Weiss, Langmuir, 2000, 16, 20;
60. (b) M. George and R. G. Weiss, J. Am. Chem. Soc., 2001, 123, 10 393.
61. (a) R. Wang, C. Geiger, L. H. Chen, B. Swanson and D. G. Whitten, J. Am. Chem. Soc., 2000, 122, 2399;
62. (b) D. C. Duncan and D. G. Whitten, Langmuir, 2000, 16, 2399.
63. R. P. Lyon and W. M. Atkins, J. Am. Chem. Soc., 2001, 123, 4408.
64. A. Ajayagosh and S. J. George, J. Am. Chem. Soc., 2001, 123, 5148.
65. (a) J. Makarevic, M. Jokic, B. Peric, V. Tomsic, B. Kojic-Prodic and M. Zinic, Chem.-Eur. J., 2001, 7, 3328;
66. (b) L. Frkanec, M. Jokic, J. Makarevic, K. Wolsperger andZinic, J. Am. Chem. Soc., 2002, 124, 9716.
67. 2O-DMSO at concentrations <0.3 mM;
68. (b) M. Kölbel and F. M. Menger, Chem. Commun., 2001, 275;
69. (c) M. Kölbel and F. M. Menger, Langmuir, 2001, 17, 4490.
70. Y. Y. Waguespack, S. Barnerjee, P. Ramannair, G. C. Irvin, V. T. John and G. L. McPherson, Langmuir, 2000, 16, 3036.
71. A. J. Carr, R. Melendez, S. J. Geib and A Hamilton, Tetrahedron Lett., 1998, 39, 7447.
72. C. Shi, Z. Huang, S. Kilic, J. Xu, R. M. Enick, E. J. Beckman, A. J. Carr, R. E. Melendez and A. D. Hamilton, Science, 1999, 286, 1540.
73. J.-L. Pozzo, G. M. Clavier, M. Colomès and H. Bouas-Laurent, Tetrahedron, 1997, 53, 6377;
74. 1 was first prepared by: V. K. Lagodzinski, Ann. Chem., 1905, 342, 90.
75. D. Marquis, J.-P. Desvergne and H. Bouas-Laurent, J. Org. Chem., 1995, 60, 7984.
76. G. Biesmans, G. Verbeek, B. Verschuere, M. van der Auweraer and F. C. de Schryver, Thin Solid Films, 1989, 169, 127.
77. M. van der Auweraer, G. Biesmans and F. C. de Schryver, Chem. Phys., 1988, 119, 355.
78. J. Ferguson, A. Castellan, J.-P. Desvergne and H. Bouas-Laurent, Chem. Phys. Lett., 1981, 78, 446.
79. J.-L. Pozzo, J.-P. Desvergne, G. M. Clavier, H. Bouas-Laurent, P. G. Jones and J. Perlstein, J. Chem. Soc., Perkin Trans. 2, 2001, 824.
80. F. Placin, J.-P. Desvergne, C. Belin, T. Buffeteau, B. Desbats, L. Ducasse and J. C. Lassègues, Langmuir, 2003, 19, 4563.
81. (a) H. Bouas-Laurent, A. Castellan, J.-P. Desvergne and R. Lapouyade, Chem. Soc. Rev., 2000, 29, 43;
82. (b) H. Bouas-Laurent, A. Castellan, J.-P. Desvergne and R. Lapouyade, Chem. Soc. Rev., 2001, 30, 248;
83. (c) H. Bouas-Laurent and J.-P. Desvergne, in Photochromism, Molecules and Systems (revised edition), eds. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 2003, ch. 14, pp 561-630.
84. Y. Ono, K. Nakashima, M. Sano, Y. Kanekiyo, K. Inoue, J. Hojo and S. Shinkai, Chem. Commun., 1998, 1477.
85. J. H. Jung, M. Amaike and S. Shinkai, Chem. Commun., 2000, 2343.
86. K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda and S. Shinkai, J. Am. Chem. Soc., 1994, 116, 6664.
87. K. Hanabusa, K. Okui, K. Karaki, M. Kimura and H. Shirai, J. Colloid Interface Sci., 1997, 195, 86.
88. K. Yoza, N. Amanokura, Y. Ono, T. Akao, H. Shinmori, M. Takeuchi, S. Shinkai and D. N. Rheinhoudt, Chem.-Eur. J., 1999, 5, 2722.
89. L. N. Lucas, PhD Thesis, Groningen, The Netherlands, 2001.
90. F. Lahmani, A. Zehnacker, J.-P. Desvergne, H. Bouas-Laurent, M. Colomès and A. Krueger, J. Photochem. Photobiol. A, 1998, 113, 203.
91. T. Brotin, J. Waluk, J.-P. Desvergne, H. Bouas-Laurent and J. Michl, Photochem. Photobiol., 1992, 55, 335.
92. (a) P. W. Atkins, Physical Chemistry, Oxford University Press, 5th edn. 1994, pp. 226-227;
93. (b) J. E. Eldridge and J. D. Ferry, J. Phys. Chem., 1954, 58, 992.