Structure and dynamics of a molecular hydrogel derived from a tripodal cholamide

Journal of the American Chemical Society

Volumn 126, Issue 48, 2004, Pages 15905-15914

  Mukhopadhyay, Samrat ^a   Maitra, Uday ^a   Ira, ^b   Krishnamoorthy, Guruswamy ^b   Schmidt, Judith ^c   Talmon, Yeshayahu ^c  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b TATA INSTITUTE OF FUNDAMENTAL RESEARCH   (India)

^c TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; BROWNIAN MOVEMENT; FLUORESCENCE; LIGHT SCATTERING; SOLUTIONS; TRANSMISSION ELECTRON MICROSCOPY;

CIRCULAR DICHROISM (CD); MINIMUM GEL CONCENTRATION (MGC); TIME-RESOLVED FLUORESCENCE;

HYDROGELS;

AMIDE; OXYGEN; PYRENE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONCENTRATION RESPONSE; GELATION; HYDROGEL; MOLECULAR DYNAMICS; REACTION ANALYSIS; STRUCTURE ANALYSIS; VISCOSITY;

EID: 10044229641     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja046788t     Document Type: Article

References (83)

1. (a) Terech, P. Encyclopedia of Surface and Colloid Science; Marcel Dekker: New York, 2002; pp 2299-2319.
2. (b) Guenet J. M. Thermoreversible Gelation of Polymers and Biopolymers; Academic Press: New York, 1992.
3. Molecular Gels; Terech, P., Wiess, R. G., Eds.; Kluwer Academic Publishers: The Netherlands, 2004.
4. For recent reviews on organogels, see: (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133. (b) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263. (c) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237. (d) See ref 2.
5. For recent reviews on organogels, see: (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133. (b) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263. (c) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237. (d) See ref 2.
6. For recent reviews on organogels, see: (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133. (b) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263. (c) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237. (d) See ref 2.
7. For recent reviews on organogels, see: (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133. (b) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263. (c) Abdallah, D. J.; Weiss, R. G. Adv. Mater. 2000, 12, 1237. (d) See ref 2.
8. (a) Bhattacharya, S.; Maitra, U.; Mukhopadhyay, S.; Srivastava, A. In Molecular Gels; Terech, P., Wiess, R. G., Eds.; Kluwer Academic Publishers: The Netherlands, 2004.
9. (b) Estroff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 104, 1201.
10. (a) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414.
11. (b) Fuhrhop, J.-H.; Spiroski, D.; Boettcher, C. J. Am. Chem. Soc. 1993, 115, 1600,
12. (c) Menger, F. M.; Caran, K. L. J. Am. Chem. Soc. 2000, 122, 11679.
13. (d) Estroff, L. A.; Hamilton, A. D. Angew. Chem., Int. Ed. 2000, 39, 3447.
14. (e) Frkanec, L.; Jokic, M.; Makarevic, J.; Wolsperger, K.; Zinic, M. J. Am. Chem. Soc. 2002, 124, 9716.
15. (f) Suzuki, M.; Yumoto, M.; Kimura, M.; Shirai, H.; Hanabusa, K. Chem. Commun. 2002, 884.
16. (g) Heeres, A.; van der Pol, C.; Stuart, M.; Friggeri, A.; Feringa, B. L.; van Esch, J. J. Am. Chem. Soc. 2003, 125, 14252,
17. (h) Suzuki, M.; Yumoto, M.; Kimura, M.; Shirai, H.; Hanabusa, K. Chem. - Eur. J. 2003, 9, 348.
18. van Bommel, K. J. C.; van der Pol, C.; Muizebelt, I.; Friggeri, A.; Heeres, A.; Meetsma, A.; Feringa, B. L.; van Esch, J. Angew. Chem., Int. Ed. 2004, 43, 1663.
19. (a) Hartgerink, J. D.; Beniash, E.; Stupp, S. I. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5133.
20. (b) Aggeli, A.; Bell, M.; Boden, N.; Keen, J. N.; Knowles, P. F.; McLeish, T. C. B.; Pitkeathly, M.; Radford, S. E. Nature 1997, 386, 259,
21. (c) Collier, J. H.; Hu, B.-H.; Ruberti, J. W.; Zhang, J.; Shum, P.; Thompson, D. H.; Messersmith, P. B. J. Am. Chem. Soc. 2001, 123, 9463.
22. (d) Xing, B.; Yu, C.-W.; Chow, K.-H.; Ho, P.-L.; Fu, D.; Xu, B. J. Am. Chem. Soc. 2002, 124, 14846.
23. (e) Schneider, J. P.; Pochan, D. J.; Ozbas, B.; Rajagopal, K.; Pakstis, L.; Kretsinger, J. J. Am. Chem. Soc. 2002, 124, 15030.
24. (f) Pochan, D. J.; Schneider, J. P.; Kretsinger, J.; Ozbas, B.; Rajagopal, K.; Haines, L. J. Am. Chem. Soc. 2003, 125, 11802.
25. (g) Claussen, R. C.; Rabatic, B. M.; Stupp, S. I. J. Am. Chem. Soc. 2003, 125, 12680.
26. (a) Pfannemuller, B.; Welte, W. Chem. Phys. Lipids 1985, 37, 227.
27. (b) Furhorp, J.-H.; Schnieder, P.; Rosenberg, J.; Boekema, E. J. Am. Chem. Soc. 1987, 109, 3387.
28. (c) Bhattacharya, S.; Acharya, S. N. G. Chem. Mater. 1999, 11, 3504.
29. (d) Kobayashi, H.; Friggeri, A.; Koumoto, K.; Amaike, M.; Shinkai, S.; Reinhoudt, D. N. Org. Lett. 2002, 4, 1423.
30. (e) Jung, J. H.; Shinkai, S.; Shimizu, T. Chem. - Eur. J. 2002, 8, 2684,
31. (f) Kiyonaka, S.; Shinkai, S.; Hamachi, I. Chem. - Eur, J. 2003, 9, 976.
32. (a) Newkome, G. R.; Baker, G. R.; Arai, S.; Saunders, M. J.; Russo, P. S.; Theriot, K. J.; Moorefield, C. N.; Rogers, L. E.; Miller, J. E.; Lieux, T. R.; Murray, M. E.; Phillips, B.; Pascal, L. J. Am. Chem. Soc. 1990, 112, 8458.
33. (b) Oda, R.; Hue, I.; Candau, S. J. Angew. Chem., Int. Ed. 1998, 37, 2689.
34. (c) Iwaura, R.; Yoshida, K.; Masuda, M.; Yase, K.; Shimizu, T. Chem. Mater. 2002, 14, 3047.
35. (d) Menger, F. M.; Peresypkin, A. J. Am. Chem. Soc. 2003, 125, 5340.
36. (a) Schryver, S. B. R. Soc. Proc., Ser. B 1914, 87, 366.
37. (b) Schryver, S. B. R. Soc Proc. Ser. B 1916, 89, 361.
38. (c) Sobotka, H.; Czeczowiczka, N. J. Colloid Sci. 1958, 13, 188.
39. (d) Rich, A.; Blow, D. M. Nature 1958, 182, 423.
40. (e) Blow, D. M.; Rich, A. J. Am. Chem. Soc. 1960, 82, 3566.
41. (f) Igimi, H.; Carey, M. J. Lipid Res. 1980, 21, 72.
42. (g) Terech, P.; Smith, W. G.; Weiss, R. G. J. Chem. Soc., Faraday Trans. 1996, 92, 3157.
43. (h) Jover, A.; Meijide, F.; Núñez, E. R.; Tato, J. V. Langmuir 1996, 12, 1789.
44. (i) Lopez, F.; Samseth, J.; Mortensen, K.; Rosenqvist, E.; Rouch, J. Langmuir 1996, 12, 6188.
45. (a) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827.
46. (b) Haines, S. R.; Harrison, R. G. Chem. Commun. 2002, 2846.
47. (c) Marmillon, C.; Gauffre, F.; Gulik-Krzywicki, T.; Loup, C.; Caminade, A.-M.; Majoral, J.-P.; Vors, J.-P.; Rump, E. Angew. Chem., Int. Ed. 2001, 40, 2626.
48. (d) Park, S. M.; Lee, Y. S.; Kim, B. H. Chem. Commun. 2003, 2912.
49. (a) Lee, K. Y.; Moony, D. J. Chem, Rev. 2001, 101, 1869.
50. (b) Miyata, T.; Uragami, T.; Nakamae, K. Adv. Drug Delivery Rev. 2002, 54, 79.
51. (c) Kiyonaka, S.; Sada, K.; Yoshimura, I.; Shinkai, S.; Kato, N.; Hamachi, I. Nat. Mater. 2004, 3, 58.
52. Tiller, J. C. Angew Chem., Int. Ed. 2003, 42, 3072.
53. Ross-Murphy, S. B. Physical Techniques for the Study of Food Biopolymers; Blackie: London, 1994.
54. Maitra, U.; Mukhopadhyay, S.; Sarkar, A.; Rao, P.; Indi, S. S. Angew. Chem., Int. Ed. 2001, 40, 2281.
55. Mukhopadhyay, S.; Ira; Krishnamoorthy, G.; Maitra, U. J. Phys. Chem. B. 2003, 107, 2189.
56. Gundiah, G.; Mukhopadhyay, S.; Tumkurkar, U. G.; Govindaraj, A.; Maitra, U.; Rao, C. N. R. J. Mater. Chem. 2003, 13, 2118.
57. Partial gelations could still be observed at micromolar concentrations (75 μM) of 1, but these gels were unstable at room temperature.
58. (a) Kalyanasundaram, K. In Photochemistry in Organized & Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991; Chapter 2.
59. (b) Bohne, C.; Redmond, R. W.; Scaiano, J. C. In Photochemistry in Organized & Constrained Media; Ramamurthy, V., Ed.; VCH Publishers; New York. 1991; Chapter 3.
60. (c) Kalyansundaram, K.; Thomas, J. K. J. Am. Chem. Soc. 1977, 99, 2039.
61. (d) Gouin, S.; Zhu, X. X. Langmuir 1998, 14, 4025.
62. Sahoo, L.; Sarangi, J.; Misra, P. K. Bull. Chem. Soc. Jpn. 2002, 75, 859.
63. Kweon, M.; Lee, Y. H.; Ahn, B. T.; Lee, M. Bull. Korean Chem. Soc. 1996, 17, 158.
64. (a) Nakajima, A. Bull. Chem. Soc. Jpn. 1973, 46, 2602.
65. (b) Hara, K.; Ware, W. Chem. Phys. 1981, 51, 61.
66. (c) Karpovich, D. S.; Blanchard, G. J. J. Phys. Chem. 1995, 99, 3951.
67. Slavik, J. Biochim. Biophys. Acta 1982, 694, 1.
68. Lakowicz, J. R. Principles of Fluorescence Spectroscope; Plenum Press: New York, 1999.
69. (a) Maitra, U.; Kumar, P. V.; Chandra, N.; D'Souza, L. J.; Prasann, M. D.; Raju, A. R. Chem. Commun. 1999, 595.
70. (b) Maitra, U.; Kumar, P. V.; Sangeetha, N. M.; Babu, P.; Raju, A. R. Tetrahedron: Asymmetry 2001, 12, 477.
71. (c) Babu, P.; Sanseetha, N. M.; Kumar, P. V.; Maitra, U.; Rissanen, K.; Raju, A. R. Chem. - Eur. J. 2003, 9, 1922.
72. (a) Saxena, A.; Udgaonkar, J. B.; Krishnamoorthy, G. In Applications of Fluorescence Spectroscopy; Hof, M., Ed.; Springer-Verlag: New York, 2004.
73. (b) Krishnamoorthy, G. Indian J. Biochem. Biophys. 2003, 40, 147.
74. (c) Maiti, N. C.; Krishna, M. M. G.; Britto, P. J.; Periasamy, N. J. Phys. Chem. B 1997, 101, 11051.
75. (d) Lakshmikanth, G. S.; Krishnamoorthy, G. Biophys. J. 1999, 77, 1100.
76. Rotational relaxation time of ANS was estimated to be 161 ns (using the Perrin equation) in pure glycerol at 22.6°C: Treloar, F. E. Chem. Scr. 1976, 10, 215.
77. Cortese, F.; Bauman, L. J. Am. Chem. Soc. 1935, 57, 1393.
78. Takahashi, A.; Sakai, M.; Kato, T. Polym. J. 1980, 12, 335.
79. (a) Talmon, Y. Cryogenic Temperature Transmission Electron Microscopy in the Study of Surfactant Systems. In Modern Characterization Methods of Surfactant Systems; Binks, B. P., Ed.; Marcel Dekker: New York, 1999; Chapter 5, pp 147-178.
80. (b) Estroff, L. A.; Leiserowitz, L.; Addadi, L.; Weiner, S.; Hamilton, A. D. Adv. Mater. 2003, 15, 38.
81. Vethamathu, M. S.; Almgren, M.; Mukhtar, E.; Bahadur, P. Langmuir 1992, 8, 2396.
82. (a) Ludescher, R. D.; Peting, L.; Hudson, S.; Hudson, B. Biophys. Chem. 1987, 28, 59.
83. (b) Srivastava, A.; Krishnamoorthy, G. Arch. Biochem. Biophys. 1997, 340, 159.