Evidence of intercolumnar π-π stacking interactions in amino-acid-based low-molecular-weight organogels

Langmuir

Volumn 26, Issue 22, 2010, Pages 16818-16827

  Allix, Florent ^a   Curcio, Pasquale ^a   Pham, Quoc Nghi ^a   Pickaert, Guillaume ^a   Jamart Grégoire, Brigitte ^a  

^a LAB DE CHIM PHYS MACROMOLECULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ASSEMBLY PROCESS; ASSOCIATION STATE; FIBRILLAR NETWORKS; GELATORS; HYDROGEN BOND NETWORKS; L-PHENYLALANINE; LOW MOLECULAR WEIGHT; NMR SPECTRUM; NMR STUDIES; ORGANO-GELATOR; ORGANOGELS; STACKING INTERACTION; SUPRAMOLECULAR AGGREGATES; SUPRAMOLECULAR ORGANIZATIONS; TEMPERATURE DEPENDENT;

AMINO ACIDS; GELATION; HYDROGEN; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY; TOLUENE;

COAGULATION;

AMINO ACID;

ARTICLE; CHEMISTRY; GEL; INFRARED SPECTROSCOPY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEMPERATURE;

AMINO ACIDS; GELS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR WEIGHT; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE;

EID: 78650326430     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la102864y     Document Type: Article

References (63)

1. (a) Vintiloiu, A.; Leroux, J.-C. J. Controlled Release 2008, 125, 179-192.
2. (b) Sangeetha, N. M.; Maitra, U. Chem. Soc. Rev. 2005, 34, 821-836.
3. (c) Llusar, M.; Sanchez, C. Chem. Mater. 2008, 20, 782-820.
4. (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3160.
5. (b) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237-1247.
6. (c) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263-2266.
7. (d) Fages, F.; Vögtle, F.; Zinic, M. Top. Curr. Chem. 2005, 256, 77-131.
8. (e) Weiss, R. G.; Terech, P. Molecular Gels: Materials with Self-Assembled Fibrillar Networks; Kluwer Academic: Norwell, MA, 2005.
9. (a) van Esch, J. H. Langmuir 2009, 25, 8392-8394.
10. (b) Hanabusa, K.; Yamada, M.; Kimura, M.; Shirai, H. Angew. Chem., Int. Ed. 1996, 35, 1949-1951.
11. (a) Melendez, R. E.; Carr, A. J.; Linton, B. R.; Hamilton, A. D. Struct. Bonding (Berlin, Ger.) 2000, 96, 31-61.
12. (b) Ishii, T.; Shinkai, S. Top. Curr. Chem. 2005, 258, 119-160.
13. Estroff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 104, 1201-1217.
14. (a) Chen, Y.; Lv, Y.; Han, Y.; Zhu, B.; Zhang, F.; Bo, Z.; Liu, C.-Y. Langmuir 2009, 25, 8548-8555.
15. (b) Debnath, S.; Shome, A.; Dutta, S.; Das, P. K. Chem.-Eur. J. 2008, 14, 6870-6881.
16. (c) Nam, S. R.; Lee, H. Y.; Hong, J.-I. Tetrahedron 2008, 64, 10531-10537.
17. (d) Zhou, Y.; Xu, M.; Wu, J.; Yi, T.; Han, J.; Xiao, S.; Li, F.; Huang, C. J. Phys. Org. Chem. 2008, 21, 338-343.
18. (e) Chow, H.-F.; Zhang, J.; Lo, C.-M.; Cheung, S.-Y.; Wong, K.-W. Tetrahedron 2007, 63, 363-373.
19. (f) Chow, H.-F.; Wang, G.-X. Tetrahedron 2007, 63, 7407-7418.
20. (g) Sureshan, K. M.; Yamaguchi, K.; Sei, Y.; Watanabe, Y. Eur. J. Org. Chem. 2004, 4703-4709.
21. (h) Makarevic, J.; Jokic, M.; Raza, Z.; Stefanic, Z.; Kojic-Prodic, B.; Zinic, M. Chem.-Eur. J. 2003, 9, 5567-5580.
22. (i) Jung, J. H.; Shinkai, S.; Shimizu, T. Chem.-Eur. J. 2002, 8, 2684-2690.
23. (j) Hanabusa, K.; Matsumoto, M.; Kimura, M.; Kakehi, A.; Shirai, H. J. Colloid Interface Sci. 2000, 224, 231-244.
24. (k) de Loos, M.; van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int Ed. 2001, 40, 613-616.
25. (a) Bielejewski, M.; Rachocki, A.; Luboradzki, R.; Tritt-Goc, J. Appl. Magn. Reson. 2008, 33, 431-438.
26. (b) Tritt-Goc, J.; Bielejewski, M.; Luboradzki, R.; Lapinski, A. Langmuir 2008, 24, 534-540.
27. (c) George, M.; Weiss, R. G. Langmuir 2003, 19, 8168-8176.
28. (d) Duncan, D. C.; Whitten, D. G. Langmuir 2000, 16, 6445-6452.
29. (e) Cassin, G.; de Costa, C.; van Duynhoven, J. P. M.; Agterof, W. G. M. Langmuir 1998, 14, 5757-5763.
30. (f) Capitani, D.; Segre, A. L.; Dreher, F.; Walde, P.; Luisi, P. L. J. Phys. Chem. 1996, 100, 15211-15217.
31. (g) Tata, M.; John, V. T.; Waguespack, Y. Y.; McPherson, G. L. J. Phys. Chem. 1994, 98, 3809-3817.
32. (h) Capitani, D.; Rossi, E.; Segre, A. L. Langmuir 1993, 9, 685-689.
33. (a) Samanta, S. K.; Pal, A.; Bhattacharya, S. Langmuir 2009, 25, 8567-8578.
34. (b) Xue, P.; Lu, R.; Chen, G.; Zhang, Y.; Nomoto, H.; Takafuji, M.; Ihara, H. Chem.-Eur. J. 2007, 13, 8231-8239.
35. (c) Kral, V.; Pataridis, S.; Setnicka, V.; Zaruba, K.; Urbanova, M.; Volka, K. Tetrahedron 2005, 61, 5499-5506.
36. (d) Rizkov, D.; Gun, J.; Lev, O.; Sicsic, R.; Melmann, A. Langmuir 2005, 21, 12130-12138.
37. (e) Sakurai, K.; Jeong, Y.; Koumoto, K.; Friggeri, A.; Gronwald, O.; Sakurai, S.; Okamoto, S.; Inoue, K.; Shinkai, S. Langmuir 2003, 19, 8211-8217.
38. (f) Terech, P.; Rossat, C.; Volino, F. J. Colloid Interface Sci. 2000, 227, 363-370.
39. (a) Escuder, B.; LLusar, M.; Miravet, J. F. J. Org. Chem. 2006, 71, 7747-7752.
40. (b) Hirst, A. R.; Coates, I. A.; Boucheteau, T. R.; Miravet, J. F.; Escuder, B.; Castelletto, V.; Hamley, I. W.; Smith, D. K. J. Am. Chem. Soc. 2008, 130, 9113-9121.
41. Menger, F. M.; Yamasaki, Y.; Catlin, K. K.; Nishimi, T. Angew. Chem., Int. Ed. 1995, 34, 585-586.
42. (a) Brosse, N.; Barth, D.; Jamart-Gregoire, B. Tetrahedron Lett. 2004, 45, 9521-9524.
43. (b) Pham, Q. N.; Brosse, N.; Frochot, C.; Dumas, D.; Hocquet, A.; Jamart-Gregoire, B. New J. Chem. 2008, 32, 1131-1139.
44. Housecroft, C. E.; Sharpe, A. G. Inorganic Chemisrty, 3rd ed.; Pearson Prentice Hall: New York, 2008; pp 69-70.
45. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; Wiley-VCH: Weinheim, Germany, 1988; pp 313-319.
46. (a) Nikolic, A. D.; Tarjani, M.; Perisic-Janjic, N.; Petrovic, S. D. J. Mol. Struct. 1988, 174, 129-134.
47. (b) Nikolic, A. D.; Kobilarov, N. L.; Brzic, A. N. J. Mol. Struct. 1983, 99, 179-188.
48. (a) George, M.; Weiss, R. G. J. Am. Chem. Soc. 2001, 123, 10393-10394.
49. (b) Abdallah, D. J.; Sirchio, S. A.; Weiss, R. G. Langmuir 2000, 16, 7558-7561.
50. (a) Wang, R.; Geiger, C.; Chen, L.; Swanson, B.; Whitten, D. G. J. Am. Chem. Soc. 2000, 122, 2399-2400.
51. (b) Sakurai, K.; Jeong, Y.; Koumoto, K.; Friggeri, A.; Gronwald, O.; Sakurai, S.; Okamoto, S.; Inoue, K.; Shinkai, S. Langmuir 2003, 19, 8211-8217.
52. (c) Geiger, C.; Stanescu, M.; Chen, Li.; Whitten, D. G. Langmuir 1999, 15, 2241-2245.
53. (a) Kral, V.; Pataridis, S.; Setnicka, V.; Zaruba, K.; Urbanova, M.; Volka, K. Tetrahedron 2005, 61, 5499-5506.
54. (b) Huang, B.; Hirst, A. R.; Smith, D. K.; Castelletto, V.; Hamley, I. W. J. Am. Chem. Soc. 2005, 127, 7130-7139.
55. (c) Schoonbeek, F. S.; van Esch, J. V.; Hulst, R.; Kellogg, R. M.; Feringa, B. L. Chem.-Eur. J. 2000, 6, 2633-2643.
56. (d) Makarevic, J.; Jokic, M.; Raza, Z.; Stefanic, Z.; Kojic-Prodic, B.; Zinic, M. Chem.-Eur. J. 2003, 9, 5567-5580.
57. Yabuuchi, K.; Tochigi, Y.; Mizoshita, N.; Hanabusa, K.; Kato, T. Tetrahedron 2007, 63, 7358-7365.
58. (a) Iqbal, S.; Miravet, J. F.; Escuder, B. Eur. J. Org. Chem. 2008, 4580-4590.
59. (b) Mizoshita, N.; Kutsuna, T.; Hanabusa, K.; Kato, T. Chem. Commun 1999, 781-782.
60. (a) de Loos, M.; Van Esch, J.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 613-616.
61. (b) Akiyama, M.; Ohtani, T. Spectrochim. Acta, Part A 1994, 50, 317-324.
62. (c) Martin, R. B. Chem. Rev. 1996, 96, 3043-3064.
63. (d) Smulders, M. M. J.; Nieuwenhuizen, M. M. L.; de Greef, T. F. A.; van der Schoot, P.; Schenning, A. P. H. J.; Meijer, E. W. Chem.-Eur. J. 2010, 16, 362-367.