Structure-function studies of modular aromatics that form molecular organogels

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7270-7278

  Baddeley, Christopher ^a   Yan, Zhiqing ^a   King, Graham ^a   Woodward, Patrick M ^a   Badjić, Jovica D ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; MOLECULAR MECHANICS; ORGANIC SOLVENTS; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL); TRANSMISSION ELECTRON MICROSCOPY; X RAY POWDER DIFFRACTION;

3D FIBRILLAR NETWORK; ENCAPSULATING SOLVENT MOLECULES; HIERARCHICAL ASSEMBLY; SONIC WAVES;

AROMATIC COMPOUNDS;

ALCOHOL; AROMATIC COMPOUND; NITROGEN; UREA;

ANISOTROPY; ARTICLE; CONFORMATIONAL TRANSITION; GEL; GELATION; HYDROGEN BOND; INFRARED SPECTROSCOPY; MOLECULAR INTERACTION; MOLECULAR MODEL; ORGANOGEL; PHASE TRANSITION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; X RAY POWDER DIFFRACTION;

EID: 34548727335     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo071159y     Document Type: Article

References (111)

1. (a) DeRossi, D.; Kajiwara, K.; Osada, Y.; Yamauchi, A., Eds. Polymer Gels. Fundamentals and Biomedical Applications; Plenum: New York, 1991.
2. (b) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133.
3. (c) Osada, Y.; Khokhlov, A. R., Eds. Polymer Gels and Networks; Marcel Dekker Inc.: New York, 2002.
4. (d) Mallia, V. A.; Tamaoki, N. Chem. Soc. Rev. 2004, 33, 76.
5. (e) Jung, J. H.; Shinkai, S. Top. Curr. Chem. 2005, 248, 223.
6. (f) Carretti, E.; Dei, L.; Weiss, R. G. Soft Matter 2005, 1, 17-22.
7. (g) Wang, R-Y.; Liu, X-Y.; Narayanan, J.; Xiong, J-Y.; Li, J-L. J. Phys. Chem. B 2006, 110, 25797.
8. (h) Weiss, R. G.; Terech P., Eds. Molecular Gels: Materials with Self-Assembled Fibrillar Networks; Springer: Dordrecht, The Netherlands, 2006.
9. (a) Van, E. J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263.
10. (b) Suzuki, M.; Nakajima, Y.; Yumoto, M.; Kimura, M.; Shirai, H.; Hanabusa, K. Org. Biomol. Chem. 2004, 2, 1155.
11. (c) Estroff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 104, 1201.
12. (d) de Loos, M.; Feringa, B. L.; van Esch, J. H. Eur. J. Org. Chem. 2005, 17, 3615.
13. (e) Sangeetha, N. M.; Maitra, U. Chem. Soc. Rev. 2005, 34, 821.
14. (f) Hirst, A. R.; Smith, D. K.; Harrington, J. P. Chem. Eur. J. 2005, 11, 6552.
15. (g) Li, J. L.; Liu, X. Y.; Strom, C. S.; Ying, X. J. Adv. Mat. 2006, 18, 2574.
16. (h) Escuder, B.; LLusar, M.; Miravet, J. F. J. Org. Chem. 2006, 71, 7747.
17. (i) George, M.; Weiss, R. G. Acc. Chem. Res. 2006, 39, 489.
18. (j) Ballabh, A.; Trivedi, D. R.; Dastidar, P. Chem. Mater. 2006, 18, 3795.
19. (k) Weng, W.; Beck, J. B.; Jamieson, A. M.; Rowan, S. J. J. Am. Chem. Soc. 2006, 128, 11663.
20. (l) Rieth, S.; Baddeley, C.; Badjić, J. D. Soft Matter 2007, 1, 137.
21. (a) Mieden-Gundert, G.; Klein, L.; Fischer, M.; Vogtle, F.; Heuze, K.; Pozzo, J-L.; Vallier, M.; Fages, F. Angew. Chem., Int. Ed. 2001, 40, 3164.
22. (b) Malìk, S.; Maji, S. K.; Banerjee, A.; Nandi, A. K. J. Chem. Soc., Perkin Trans. 2 2002, 6, 1177.
23. (c) Potluri, V. K.; Hamilton, A. D. J. Supramol. Chem. 2003, 2, 321.
24. (d) Ishi-i, T.; Shinkai, S. Top. Curr. Chem. 2005, 258, 119.
25. (e) Serpe, M. J.; Craig, S. L. Langmuir 2007, 23, 1626.
26. (a) Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155.
27. (b) Whitesides, G. M.; Grzybowski, B. Science 2002, 295, 2418.
28. (c) Ikkala, O.; ten Brinke, G. Chem. Commun. 2004, 19, 2131.
29. (d) Lehn, J-M. In Supramolecular Polymers; Ciferri, A., Ed.; CRC Press LLC: Boca Raton, FL, 2005; p 3.
30. (e) Fialkowski, M.; Bishop, K. J. M.; Klajn, R.; Smoukov, S. K.; Campbell, C. J.; Grzybowski, B. A. J. Phys. Chem. B 2006, 110, 2482.
31. (a) Hanabusa, K.; Yamada, M.; Kimura, M.; Shirai, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1949.
32. (b) van Esch, J.; Kellogg, R. M.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 281.
33. (c) Schoonbeek, F. S.; Van Esch, J. H.; Wegewijs, B.; Rep, D. B. A.; De Haas, M. P.; Klapwijk, T. M.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed 1999, 38, 1393.
34. (d) George, M.; Snyder, S. L.; Terech, P.; Glinka, C. J.; Weiss, R. G. J. Am. Chem. Soc. 2003, 125, 10275.
35. (e) Liu, Y.; Li, Y.; Jiang, L.; Gan, H.; Liu, H.; Li, Y.; Zhuang, J.; Lu, F.; Zhu, D. J. Org. Chem. 2004, 69, 9049.
36. (f) Nie, X.; Wang, G. J. Org. Chem. 2006, 71, 4734.
37. (g) Chow, H-F.; Zhang, J.; Lo, C-M.; Cheung, S-Y.; Wong, K-W. Tetrahedron 2006, 63, 363.
38. (a) Zhu, G.; Dordick, J. S. Chem. Mater. 2006, 18, 5988.
39. (b) Pinault, T.; Isare, B.; Bouteiller, L. ChemPhysChem 2006, 7, 816.
40. (a) Flory, P. J. J. Phys. Chem. 1942, 46, 132.
41. (b) Flory, P. J. Faraday Discuss. Chem. Soc. 1974, 57, 7.
42. (a) van Esch, J.; De Feyter, S.; Kellogg, R. M.; De Schryver, F.; Feringa, B. L. Chem. Eur. J. 1997, 3, 1238.
43. (b) Van Esch, J.; Schoonbeek, F.; De Loos, M.; Kooijman, H.; Spek, A. L.; Kellogg, R. M.; Feringa, B. L. Chem. Eur. J. 1999, 5, 937.
44. (c) De Loos, M.; Ligtenbarg, A. G. J.; Van Esch, J.; Kooijman, H.; Spek, A. L.; Hage, R.; Kellogg, R. M.; Feringa, B. L. Eur. J. Org. Chem. 2000, 22, 3675-3678.
45. (d) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2001, 7, 4328.
46. (e) Mizoshita, N.; Monobe, H.; Inoue, M.; Ukon, M.; Watanabe, T.; Shimizu, Y.; Hanabusa, K.; Kato, T. Chem. Commun. 2002, 5, 428.
47. (f) George, M.; Tan, G.; John, V. T.; Weiss, R. G. Chem. Eur. J. 2005, 11, 3243.
48. (g) Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491.
49. (a) Etter, M. C.; Urbanczyk-Lipkowska, Z.; Zia-Ebrahimi, M.; Panunto, T. W. J. Am. Chem. Soc. 1990, 112, 8415.
50. (b) Masunov, A.; Dannenberg, J. J. J. Phys. Chem. B 2000, 104, 806.
51. (c) Shimizu, L. S.; Hughes, A. D.; Smith, M. D.; Davis, M. J.; Zhang, B. P.; Zur Loye, H-C.; Shimizu, K. D. J. Am. Chem. Soc. 2003, 125, 14972.
52. (d) Laliberte, D.; Maris, T.; Wuest, J. D. Can. J. Chem. 2004, 82, 386.
53. Etter, M. C. Acc. Chem. Res. 1990, 23, 120.
54. (a) Jadzyn, J.; Stockhausen, M.; Zywucki, B. J. Phys. Chem. 1987, 91, 754.
55. (b) Lortie, F.; Boileau, S.; Bouteiller, L. Chem. Eur. J. 2003, 9, 3008.
56. (c) Simić, V.; Bouteiller, L.; Jalabert, M. J. Am. Chem. Soc. 2003, 125, 13148.
57. (d) Bouteiller, L.; Colombani, O.; Lortie, F.; Terech, P. J. Am. Chem. Soc. 2005, 127, 8893.
58. Badjić, J. D.; Nelson, A.; Cantrill, S. J.; Turnbull, W. B.; Stoddart, J. F. Acc. Chem. Res. 2005, 38, 723.
59. (a) Xia, T. K.; Landman, U. Science 1993, 261, 1310.
60. (b) Song, J.; Hollingsworth, R. I. J. Am. Chem. Soc. 1999, 121, 1851.
61. (c) Xie, Z. X.; Xu, X.; Tang, J.; Mao, B. W. Chem. Phys. Lett. 2000, 323, 209.
62. (a) Tsuda, K.; Ikekawa, N.; Mishima, H.; Ilino, A.; Morishage, T. Pharm. Bull. Jpn. 1953, 1, 122.
63. (b) Mathia, J.; Seto, C.; Simanek, E.; Whitesides, G. M. J. Am. Chem. Soc. 1994, 116, 1725.
64. (c) Starnes, S. D.; Rudkevich, D. M.; Rebek, J., Jr. J. Am. Chem. Soc. 2001, 123, 4659.
65. (d) Collman, J. P.; Decreau, R. A.; Constanzo, S. Org. Lett. 2004, 6, 1033.
66. (e) Tsuge, A.; Matsubara, A.; Moriguchi, T. Tetrahedron Lett. 2006, 37, 6607.
67. For an example of the ultrasound promoted sol-gel phase transition, see: Naota, T.; Koori, H. J. Am. Chem. Soc. 2005, 127, 9324.
68. (a) Paulusse, J. M. J.; Sijbesma, R. P. Angew. Chem., Int. Ed. 2006, 45, 2334.
69. (b) Paulusse, J. M. J.; Huijbers, J. P. J.; Sijbesma, R. P. Chem. Eur. J. 2006, 12, 4928.
70. The concept of dynamic combinatorial chemistry is based on the fast exchange of various host-guest thermodynamic states. See: (a) Rowan, S. J.; Cantrill, S. J.; Cousins, G. R. L.; Sanders, J. K. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2002, 41, 899.
71. (b) Corbett. P. T.; Leclaire. J.; Vial, L.; West, K. R.; Wietor, J-L.; Sanders, J. K. M.; Otto, S. Chem. Rev. 2006, 106, 3652.
72. Huang, X.; Terech, P.; Raghavan, S. R.; Weiss, R. G. J. Am. Chem. Soc. 2005, 127, 4336.
73. Coelho, A. A. Topas Academic, General Profile and Structure Analysis Software for Powder Diffraction Data; Bruker AXS: Karlsruhe, Germany, 2004.
74. David, W. I. F.; Shankland, K.; Shankland, N. Chem. Commun. 1998, 931-932.
75. David, W. I. F.; Shankland, K.; van de Streek, J.; Pidcock, E.; Motherwell, W. D. S.; Cole, J. C. J. Appl. Crystallogr. 2006, 39, 910-915.
76. (a) Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc. Perkin Trans. 2 2001, 5, 651.
77. (b) Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210.
78. Feiters, M. C.; Nolte, R. J. M. Adv. Supramol. Chem. 2000, 6, 41.
79. (a) Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127.
80. (b) Allinger, N. L.; Kok, R. A.; Imam, M. R. J. Comput. Chem. 1988, 9, 591.
81. (a) Rebek, J. Jr. Science 1987, 235, 1478.
82. (b) Cram, D. J. Science 1988, 240, 760.
83. Cram, D. J Angew. Chem. 1986, 98, 1041.
84. Cannon, W. R.; Madura, J. D.; Thummel, R. P.; McCammon, J. A. J. Am. Chem. Soc. 1993, 115, 879.
85. (a) Kontoyianni, M.; Bowen, J. P. J. Comput. Chem. 1992, 13, 657.
86. (b) Galabov, B.; Ilieva, S.; Hadjieva, B.; Dudev, T. J. Mol. Struct. 1997, 407, 47-51.
87. (c) Lecomte, F.; Lucas, B.; Gregoire, G.; Schermann, J. P.; Desfrancois, C. Phys. Chem. Chem. Phys. 2003, 5, 3120.
88. (d) Custelcean, R.; Gorbunova, M. G.; Bonnesen, P. V. Chem. Eur. J. 2005, 11, 1459.
89. (a) Rao, C. N. R.; Rao, K. G.; Goel, A.; Balasubramanian, D. J. Chem. Soc. A 1971, 19, 3077.
90. (b) Mido, Y. Spectrochim. Acta 1973, 29.
91. (c) Mido, Y. Bull. Chem. Soc. Jpn. 1974, 47, 1833.
92. (d) Mido, Y.; Gohda, T. Bull. Chem. Soc. Jpn. 1975, 48, 2704.
93. (a) Filleux-Blanchard, M. L.; Durand, A. Org. Magn. Reson. 1971, 3, 187.
94. (b) Olofsson, G.; Stilbs, P.; Drakenberg, T.; Forsen, S. Tetrahedron 1971, 27, 4583.
95. (c) Hartman, J. S.; Schrobilgen, G. J. Can. J. Chem. 1973, 51, 99.
96. Anet, F. A. L.; Ghiaci, M. J. Am. Chem. Soc. 1979, 101, 6857.
97. (a) Haushalter, K. A.; Lau, J.; Roberts, J. D. J. Am. Chem. Soc. 1996, 118, 8891.
98. (b) Kurth, T. L.; Lewis, F. D. J. Am. Chem. Soc. 2003, 125, 13760.
99. (c) Bryantsev, V. S.; Firman, T. K.; Hay, B. P. J. Phys. Chem. A 2005, 109, 832.
100. (a) Weiner, P. K.; Kollman, P. A. J. Comput. Chem. 1981, 2, 287.
101. (b) Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spellmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179.
102. (a) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart. J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
103. (b) Kamieth, M.; Klärner, F.-G.; Diederich, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 3303.
104. (a) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525.
105. (b) Cockroft, S. L.; Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Am. Chem. Soc. 2005, 127, 8594.
106. (a) Cozzi, F.; Siegel, J. S. Pure Appl. Chem. 1995, 67, 693.
107. (b) Rashkin, M. J.; Waters, M. L. J. Am. Chem. Soc. 2002, 124, 1860.
108. (a) Terech, P.; Ostuni, E.; Weiss, R. G. J. Phys. Chem. 1996, 100, 3759.
109. (b) Ostuni, E.; Kamaras, P.; Weiss, R. Angew. Chem., Int. Ed. Engl. 1996, 35, 1324.
110. (c) Sakurai, K.; Jeong, Y.; Koumoto, K.; Friggeri, A.; Gronwald, O.; Sakurai, S.; Okamoto, S.; lnoue, K.; Shinkai, S. Langmuir 2003, 19, 8211.
111. Reichardt, C. Chem. Rev. 1994, 94, 2319.