L-lysine-based supramolecular hydrogels containing various inorganic ions

Organic and Biomolecular Chemistry

Volumn 3, Issue 16, 2005, Pages 3073-3078

  Suzuki, Masahiro ^a   Yumoto, Mariko ^a   Shirai, Hirofusa ^a   Hanabusa, Kenji ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROGELS; INORGANIC ACIDS; IONS; THERMODYNAMIC STABILITY;

ELECTRON MICROGRAPHS; GEL STRENGTHS; HYDROGELATORS; L-LYSINE-BASED SUPRAMOLECULAR HYDROGELS;

SUPRAMOLECULAR CHEMISTRY;

EID: 24144471053     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b507540h     Document Type: Article

References (76)

1. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995.
2. (a) P. Terech and R. G. Weiss, Chem. Rev., 1997, 97, 3133
3. (b) P. Terech, Ber. Bunsen-Ges. Phys. Chem., 1998, 102, 1630
4. (c) J. H. van Esch and B. L. Feringa, Angew. Chem., Int. Ed., 2000, 39, 2263
5. (d) D. J. Abdallah and R. G. Weiss, Adv. Mater., 2000, 12, 1237.
6. (a) L. Guan and Y. Zhao, Chem. Mater., 2000, 12, 3667
7. (b) M. Hashimoto, S. Ujiie and A. Mori, Adv. Mater., 2003, 15, 797
8. (c) M. Moriyama, N. Mizoshita, T. Yokota, K. Kishimoto and T. Kato, Adv. Mater., 2003, 15, 1335
9. (d) F. Camerel and C. F. J. Faul, Chem. Commun., 2003, 1958.
10. (a) J. H. van Esch and B. L. Feringa, Angew. Chem., Int. Ed., 2000, 39, 2263
11. (b) M. de Loos, J. van Esch, R. M. Kellogg and B. L. Feringa, Angew. Chem., Int. Ed., 2001, 40, 613
12. (c) G. Mieden-Gundert, L. Klein, M. Fischer, F. Vögtle, K. Heuzé, J.-L. Pozzo, M. Vallier and F. Pages, Angew. Chem., Int. Ed., 2001, 40, 3164
13. (d) H. M. Willemen, T. Vermonden, A. T. M. Marcelis and E. J. R. Sudhölter, Eur. J. Org. Chem., 2001, 2329
14. (e) K. S. Partridge, D. K. Smith, G. M. Dykes and P. T. McGrail, Chem. Commun., 2001, 319
15. (f) R. P. Lyon and W. M. Atkins, J. Am. Chem. Soc., 2001, 123, 4408
16. (g) A. Ajayaghosh and S. J. George, J. Am. Chem. Soc., 2001, 123, 5148
17. (h) U. Beginn and B. Tartsch, Chem. Commun., 2001, 1924
18. (i) A. Friggeri, O. Gronwald, K. J. C. van Bommel, S. Shinkai and D. N. Reinhoudt, J. Am. Chem. Soc., 2002, 124, 10754
19. (j) K. Yabuuchi, E. Marfo-Owusu and T. Kato, Org. Biomol. Chem., 2003, 1, 3464
20. (k) F. Würthner, S. Yao and U. Beginn, Angew. Chem., Int. Ed., 2003, 42, 3247
21. (l) P. Babu, N. M. Sangeetha, P. Vijaykumar, U. Maitra, K. Pissanen and A. R. Raju, Chem.-Eur. J., 2003, 9, 1922;
22. (m) E. Carretti, L. Dei, P. Baglioni and R. G. Weiss, J. Am. Chem. Soc, 2003, 125, 5121
23. (n) J. Makarević, M. Jokić, Z. Raza, Z. Štefanie, B. Kojić-Prodić and M. Zinic, Chem.-Eur. J., 2003, 9, 5567.
24. (a) K. Hanabusa, K. Hiratsuka, M. Kimura and H. Shirai, Chem. Mater., 1999, 11, 649
25. (b) N. Mizoshita, K. Kutsuna, K. Hanabusa and T. Kato, J. Photopolym. Sci. Technol., 2000,13, 307
26. (c) L. Gu and Y. Zhao, Chem. Mater., 2000, 12, 3667
27. (d) F Placin, J.-P. Desvergne and J.-C. Lasségus, Chem. Mater., 2001, 13, 117;
28. (e) W. Kubo, K. Murakoshi, T. Kitamura, S. Yoshida, K. Hanabusa, H. Shirai, Y. Wada and S. Yanagida, J. Phys. Chem. B, 2001, 105, 12809
29. (f) W. Kubo, T. Kitamura, K. Hanabusa, Y. Wada and S. Yanagida, Chem. Commun., 2002, 374
30. (g) Y. Shibata, T. Kato, T. Kado, R. Shiratuchi, W. Takashima, K. Kaneto and S. Hayase, Chem. Commun., 2003, 2730.
31. (a) S. Li, V. T. John, G. C. Irvin, S. H. Bachakonda, G. L. Mcpherson and C. J. O'Connor, J. Appl. Phys., 1999, 85, 5965
32. (b) N. Velasco-Garcia, M. J. Valencia-Gonzàes and M. E. Diaz-Garcia, Analyst, 1997, 122, 5008.
33. (a) W. Gu, L. Lu, G. B. Chapman and R. G. Weiss, Chem. Commun., 1997, 543
34. (b) 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
35. (c) S. Kobayashi, K. Hanabusa, N. Hamasaki, M. Kimura, H. Shirai and S. Shinkai, Chem. Mater., 2000, 12, 1523
36. (d) J. H. Jung, H. Kobayashi, M. Masuda, T. Shimizu and S. Shinkai, J. Am. Chem. Soc., 2001, 123, 8785
37. (e) J. H. Jung, S.-H. Lee, J. Shin, K. Yoshida, T. Shimizu and S. Shinkai, Chem.-Eur. J., 2003, 9, 5307
38. (f) G. Gundiah, S. Mukhopadhyay, U. G. Tumkurkar, A. Govindaraj, U. Maitra and C. N. R. Rao, J. Mater. Chem., 2003, 13, 2118.
39. (a) N. A. Peppas, Y. Huang, M. Tottes-Lugo, J. H. Ward and J. Zhang, Annu. Rev. Biomed. Eng., 2000, 2, 9
40. (b) R. Langer, Acc. Chem. Res., 2000, 33, 94
41. (c) K. Yong and D. J. Mooney, Chem. Rev., 2001, 101, 1869.
42. (a) B. Zhao and J. S. Moore, Langmuir, 2001, 17, 4758
43. (b) Y. Luo, P. D. Dalton and M. S. Shoichet, Chem. Mater., 2001, 13, 4087
44. (c) V. Pardo-Yissar, R. Gabai, A. N. Shipway, T. Bourenko and I. Willner, Adv. Mater., 2001, 13, 1320
45. (d) Z. Hu, X. Lu and J. Gao, Adv. Mater., 2001, 13, 1708.
46. (a) L. A. Estroff and A. D. Hamilton, Chem. Rev., 2004, 104, 1201 and references cited therein
47. (b) Z. Yang, H. Gu, Y. Zhang, L. Wang and B. Xu, Chem. Commun., 2004, 208
48. (c) A. D'Aleo, J.-L. Pozzo, F Fages, M. Schmutz, G. Mieden-Gundert, F. Vogtle, V. Caplar and M. Zinic, Chem. Commun., 2004, 190
49. (d) M. Suzuki, M. Yumoto, M. Kimura, H. Shirai and K. Hanabusa, Tetrahedron Lett., 2004, 45, 2947.
50. (a) Y. Zhang, H. Gu, Z. Yang and B. Xu, J. Am. Chem. Soc., 2003, 125, 13680
51. (b) D. J. Pochan, J. P. Schneider, J. Kretsinger, B. Ozbas, K. Rajagopal and L. Haines, J. Am. Chem. Soc., 2003, 125, 11802
52. (c) J. C. Tiller, Angew. Chem., Int. Ed., 2003, 42, 3072
53. (d) F. M. Menger and A. V. Peresypkin, J. Am. Chem. Soc., 2003, 125, 5340
54. (e) G. Wang and A. D. Hamilton, Chem. Commun., 2003, 310
55. (f) L. A. Estroff, L. Leiserowitz, L. Addadi, S. Weiner and A. D. Hamilton, Adv. Mater., 2003, 15, 38
56. (g) J. H. Jung, S. Shinkai and T. Shimizu, Chem.-Eur. J., 2002, 8, 2684
57. (h) H. Kobayashi, A. Friggeri, K. Koumoto, M. Amaike, S. Shinkai and D. N. Reinhoudt, Org. Lett., 2002, 4, 1423
58. (i) T. Nakashima and N. Kimizuka, Adv. Mater., 2002, 16, 1113.
59. (a) S. Bhattacharya and S. N. G. Acharya, Langmuir, 2000, 16, 87
60. (b) F. M. Menger and K. L. Caran, J. Am. Chem. Soc., 2000, 122, 11679
61. (c) L. A. Estroff and A. D. Hamilton, Angew. Chem., Int. Ed., 2001, 39, 3447
62. (d) U. Maitra, S. Mukhopadhyay, A. Sarkar, P. Rao and S. Indi, Angew. Chem., Int. Ed., 2001, 40, 2281
63. (e) M. Amaike, H. Kobayashi and S. Shinkai, Chem. Lett., 2001, 620
64. (f) J. H. Jung, G. John, M. Masuda, K. Yoshida, S. Shinkai and T. Shimizu, Langmuir, 2001, 17, 7229
65. (g) J. Makarevic, M. Kokic, B. Perić, V. Tomišic̀, B. Kojić-Prodić and M. Žinić, Chem.-Eur. J., 2001, 7, 3328.
66. (a) M. Suzuki, M. Yumoto, M. Kimura, H. Shirai and K. Hanabusa, Chem. Commun., 2002, 884
67. (b) M. Suzuki, M. Yumoto, M. Kimura, H. Shirai and K. Hanabusa, New J. Chem., 2002, 26, 817
68. (c) M. Suzuki, M. Yumoto, M. Kimura, H. Shirai and K. Hanabusa, Chem.-Eur. J., 2003, 9, 348
69. (d) M. Suzuki, M. Yumoto, M. Kimura, H. Shirai and K. Hanabusa, Helv. Chim. Acta, 2004, 87, 1.
70. 2 did not form a hydrogel even at 8 wt%.
71. W. R. Carmody, J. Chem. Educ., 1961, 38, 559.
72. (a) K. Hanabusa, K. Shimura, K. Hirose, M. Kimura and H. Shirai, Chem. Lett., 1996, 885
73. (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, 937.
74. The carbonyl group of the ester did not participate in an intermolecular hydrogen bonding interaction.
75. S. Tamaru, R. Laboradzki and S. Shinkai, Chem. Lett., 2001, 336.
76. C. F. H. Allen and A. Bell, Org. Synth. III, 1955, 846.