Organogelators from self-assembling peptide based dendrimers: structural and morphological features

Tetrahedron

Volumn 64, Issue 1, 2008, Pages 175-185

  Palui, Goutam ^a   Simon, François Xavier ^c   Schmutz, Marc ^c   Mesini, Philippe J ^c   Banerjee, Arindam ^a,b  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

^b INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^c INSTITUT CHARLES SADRON   (France)

Author keywords

Dendrimer; Gelation; Nanostructure; Self assembly

Indexed keywords

1,2 DICHLOROBENZENE; AMIDE; ASPARTIC ACID; BENZENE; CHLOROBENZENE; DENDRIMER; ESTER; HEXANOL; NITROBENZENE; ORGANIC SOLVENT; PEPTIDE DERIVATIVE; SUCCINIC ACID; TEREPHTHALIC ACID; TETRALIN DERIVATIVE; TOLUENE; XYLENE;

ARTICLE; CHEMICAL STRUCTURE; FIELD EMISSION SCANNING ELECTRON MICROSCOPY; GELATION; HEATING; HYDROGEN BOND; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; X RAY POWDER DIFFRACTION;

EID: 36348956841     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.061     Document Type: Article

References (94)

1. Terech P., and Weiss R.G. Chem. Rev. 97 (1997) 3133-3159
2. Gronwald O., Snip E., and Shinkai S. Curr. Opin. Colloid Interface Sci. 7 (2002) 148-156
3. Oda R., Huc I., and Candau S.J. Angew. Chem., Int. Ed. 37 (1998) 2689-2691
4. Abdallah D.J., and Weiss R.G. Adv. Mater. 12 (2000) 1237-1247
5. Shimizu T. Polym. J. 35 (2003) 1-22
6. Sangeetha N.M., and Maitra U. Chem. Soc. Rev. 34 (2005) 821-836
7. Yoha K., Amanokura N., Ono Y., Akao T., Shinmori H., Takeuchi M., Shinkai S., and Reinhout D.N. Chem.-Eur. J. 5 (1995) 2722-2729
8. Yoza K., Ono Y., Yoshihara K., Akao T., Shinmori H., Takeuchi M., Shinkai S., and Reinhoudt D.N. Chem. Commun. (1998) 907-908
9. Schmidt R., Michel M., Schmutz M., Decher G., and Mésini P.J. Langmuir 18 (2002) 5668-5672
10. Schmidt R., Adam F.B., Michel M., Schmutz M., Decher G., and Mésini P.J. Tetrahedron Lett. 44 (2003) 3171-3174
11. de Loops M., van Esch J., Kellogg R.M., and Feringa B.L. Angew. Chem., Int. Ed. 40 (2001) 613-616
12. Schoonbeek F.S., van Esch J.H., Hulst R., Kellogg R.M., and Feringa B.L. Chem.-Eur. J. 6 (2000) 2633-2643
13. Jeong Y., Hanabusa K., Masunaga H., Akiba I., Miyoshi K., Sakurai S., and Sakurai K. Langmuir 21 (2005) 586-594
14. Moniruzzaman M., and Sundarajan P.R. Langmuir 21 (2005) 3802-3807
15. Sangeetha N.M., Balasubramanian R., Maitra U., Ghosh S., and Raju A.R. Langmuir 18 (2002) 7154-7157
16. Willemen H.M., Marcelis A.T.M., Sudholter E.J.R., Bouwman W.G., Deme B., and Terech P. Langmuir 20 (2004) 2075-2080
17. Whitesides G.M., and Grzybowski B.A. Science 295 (2002) 2418-2421
18. Hamley I.W. Angew. Chem., Int. Ed. 42 (2003) 1692-1712
19. Elemans J.A.A.W., Rowan A.E., and Nolte R.J.M. J. Mater. Chem. 13 (2003) 2661-2670
20. An B.-K., Lee D.-S., Lee J.-S., Park Y.-S., Song H.-S., and Park S.Y. J. Am. Chem. Soc. 126 (2004) 10232-10233
21. Xing B., Choi M.-F., and Xu B. Chem. Commun. (2002) 362-363
22. Ihara H., Sakurai T., Yamada T., Hashimoto T., Takafuji M., Sagawa T., and Hachisako H. Langmuir 18 (2002) 7120-7123
23. Beck J.B., and Rowan S.J. J. Am. Chem. Soc. 125 (2003) 13922-13923
24. Ziessel R., Pickaert G., Camerel F., Donnio B., Guillon D., Cesario M., and Prangé T. J. Am. Chem. Soc. 126 (2004) 12403-12413
25. Kuroiwa K., Shibata T., Takada A., Nemoto N., and Kimizuka N. J. Am. Chem. Soc. 126 (2004) 2016-2021
26. Sugiyasu K., Numata M., Fujita N., Park S.M., Yun Y.J., Kim B.H., and Shinkai S. Chem. Commun. (2004) 1996-1997
27. Sugiyasu K., Fujita N., Takeuchi M., Yamada S., and Shinkai S. Org. Biomol. Chem. 1 (2003) 895-899
28. Kawano S., Fujita N., and Shinkai S. Chem. Commun. (2003) 1352-1353
29. Pozzo J.-L., Desvergne J.-P., Clavier G.M., Bouas-Laurent H., Jones P.G., and Perlstein J. J. Chem. Soc., Perkin Trans. 2 (2001) 824-826
30. Placin F., Desvergne J.-P., and Lassègues J.-C. Chem. Mater. 13 (2001) 117-121
31. Xue P., Lu R., Li D., Jin M., Bao C., Zhao Y., and Wang Z. Chem. Mater. 16 (2004) 3702-3707
32. Jung J.H., Kobayashi H., Masuda M., Shimizu T., and Shinkai S. J. Am. Chem. Soc. 123 (2001) 8785-8789
33. Lu L., and Weiss R.G. Chem. Commun. (1996) 2029-2030
34. Lin Y.-C., Kachar B., and Weiss R.G. J. Am. Chem. Soc. 111 (1989) 5542-5551
35. George M., Snyder S.L., Terech P., Glinka C.J., and Weiss R.G. J. Am. Chem. Soc. 125 (2003) 10275-10283
36. George M., and Weiss R.G. Chem. Mater. 15 (2003) 2879-2888
37. Abdallah D.J., Lu L., and Weiss R.G. Chem. Mater. 11 (1999) 2907-2911
38. Abdallah D.J., and Weiss R.G. Langmuir 16 (2000) 352-355
39. Jung J.H., Nakashima K., and Shinkai S. Nano Lett. 1 (2001) 145-148
40. Jung J.H., Kobayashi H., van Bommel K.J.C., Shinkai S., and Shimizu T. Chem. Mater. 14 (2002) 1445-1447
41. Xue P., Lu R., Huang Y., Jin M., Tan C., Bao C., Wang Z., and Zhao Y. Langmuir 20 (2004) 6470-6475
42. Xue P., Lu R., Li D., Jin M., Tan C., Bao C., Wang Z., and Zhao Y. Langmuir 20 (2004) 11234-11239
43. Shumburo A., and Biewer M.C. Chem. Mater. 14 (2002) 3745-3750
44. Ray S., Das A.K., and Banerjee A. Chem. Commun. (2006) 2816-2818
45. Sugiyasu K., Fujita N., and Shinkai S. Angew. Chem., Int. Ed. 43 (2004) 1229-1233
46. Ajayaghosh A., George S.J., and Praveen V.K. Angew. Chem., Int. Ed. 42 (2003) 332-335
47. van Esch J.H., and Feringa B.L. Angew. Chem., Int. Ed. 39 (2000) 2263-2266
48. Wilder E.A., Wilson K.S., Quinn J.B., Skrtic D., and Antonucci J.M. Chem. Mater. 17 (2005) 2946-2952
49. Kubo W., Kitamura T., Hanabusa K., Wada Y., and Yanagida S. Chem. Commun. (2002) 374-377
50. Kanie K., and Sugimoto T. Chem. Commun. (2004) 1584-1585
51. Raj C.R., and Jana B.K. Chem. Commun. (2005) 2005-2007
52. Love C.S., Chechik V., Smith D.K., Wilson K., Ashworth I., and Brennan C. Chem. Commun. (2005) 1971-1973
53. Kim J., Altreute D.H., Clark D.S., and Dordick J.S. J. Am. Oil Chem. Soc. 75 (1998) 1109-1113
54. Smith D.K. Adv. Mater. 18 (2006) 2773-2778
55. Tomalia D.A. Aldrichimica Acta 37 (2004) 39-57
56. Frechet J.M.J. J. Polym. Sci., Part A 41 (2003) 3713-3725
57. Newkome G.R., Baker G.R., Saunders M.J., Russo P.S., Gupta V.K., Yao Z.Q., Miller J.E., and Bouillion K. J. Chem. Soc., Chem. Commun. (1986) 752-753
58. 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., and Pascal L. J. Am. Chem. Soc. 112 (1990) 8459-8465
59. Newkome G.R., Lin X.F., Yaxiong C., and Escamilla G.H. J. Org. Chem. 58 (1993) 3123-3129
60. Newkome G.R., Moorefield C.N., Baker G.R., Behera R.K., Escamilla G.H., and Saunders M.J. Angew. Chem., Int. Ed. Engl. 31 (1992) 917-919
61. Yu K.H., Russo P.S., Younger L., Henk W.G., Hua D.W., Newkome G.R., and Baker G. J. Polym. Sci., Polym. Phys. 35 (1997) 2787-2793
62. Jang W.D., Jiang D.L., and Aida T. J. Am. Chem. Soc. 122 (2000) 3232-3233
63. Jang W.D., and Aida T. Macromolecules 36 (2003) 8461-8469
64. Zhang W., Gonzalez S.O., and Simanek E.E. Macromolecules 35 (2002) 9015-9021
65. Mulders S.J.E., Brouwer A.J., and Liskamp R.M.J. Tetrahedron Lett. 38 (1997) 3085-3088
66. Prevote D., Le R.-G.S., Caminade A.-M., Masson S., and Majoral J.-P. Synthesis (1997) 1199-1207
67. Kayser B., Altman J., and Beck W. Chem.-Eur. J. 5 (1999) 754-758
68. Sadler K., and Tam J.P. Rev. Mol. Biotechnol. 90 (2002) 195-229
69. Kolhe P., Misra E., Kannan S., L-Lai M., and Kannan R.M. Int. J. Pharm. 259 (2003) 143-160
70. Smith D.K., and Diederich F. Chem.-Eur. J. 4 (1998) 1353-1361
71. Hirst A.R., Smith D.K., Feiters M.C., and Geurts H.P.M. Langmuir 20 (2004) 7070-7077
72. Love C.S., Hirst A.R., Chechik V., Smith D.K., Ashworth I., and Brennan C. Langmuir 20 (2004) 6580-6585
73. Partridge K.S., Smith D.K., Dykes G.M., and McGrail P.T. Chem. Commun. (2001) 319-320
74. Hirst A.R., Smith D.K., Feiters M.C., Geurts H.P.M., and Wright A.C. J. Am. Chem. Soc. 125 (2003) 9010-9011
75. Hirst A.R., Smith D.K., Feiters M.C., and Geurts H.P.M. Chem.-Eur. J. 10 (2004) 5901-5910
76. Ranganathan D., Kurur S., Gilardi R., and Karle I.L. Biopolymers 54 (2000) 289-295
77. Ji Y., Luo Y.-F., Jia X.-R., Chen E.-Q., Huang Y., Ye C., Wang B.-B., Zhou Q.-F., and Wei Y. Angew. Chem., Int. Ed. 44 (2005) 6025-6029
78. Li Y., Wang T., and Liu M. Tetrahedron 63 (2007) 7468-7473
79. Kim C., Kim K.T., Chang Y.H., Song H., Cho T.Y., and Jeon H.J. J. Am. Chem. Soc. 123 (2001) 5586-5587
80. Kim C., Lee S.J., Lee I.H., and Kim K.T. Chem. Mater. 15 (2003) 3638-3642
81. Bodanszky M., and Bodanszky A. The Practice of Peptide Synthesis (1984), Springer, New York, NY pp 1-282
82. Garner M.C., Terech P., Aiiegraud J.-J., Mistrot B., Nguyen P., de Geyer A., and Rivera D. J. Chem. Soc., Faraday Trans. 94 (1998) 2173-2179
83. Li Y., Yan D., and Zhou E. Colloid Polym. Sci. 280 (2002) 124-129
84. Skrovanek D.J., Painter P.C., and Coleman M.M. Macromolecules 19 (1986) 699-705
85. Spencer J.N., Berger S.K., Powell C.R., Henning B.D., Furman G.S., Loffredo W.M., Rydberg E.M., Neubert R.A., Shoop C.E., and Blauch D.N. J. Phys. Chem. 85 (1981) 1236-1241
86. Huang X., Raghavan R.S., Terech P., and Weiss G.R. J. Am. Chem. Soc. 128 (2006) 15334-15352
87. Ramachandran G.N., and Kartha G. Nature 179 (1955) 593-594
88. Eyre D.R. Science 207 (1980) 1315-1322
89. Pouling L., Corey R.B., and Branson H.R. Proc. Natl. Acad. Sci. U.S.A. 37 (1951) 205-211
90. Watson J.D., and Crick F.H.C. Nature 171 (1953) 737-738
91. Hirst A.R., Smith D.K., and Harrington J.P. Chem.-Eur. J. 11 (2005) 6552-6559
92. Zhou Y., Yi T., Li T., Zhou Z., Li F., Huang W., and Huang C. Chem. Mater. 18 (2006) 2974-2981
93. Zhu G., and Dordick J.S. Chem. Mater. 18 (2006) 5988-5995
94. Malik S., Kawano S., Fujita N., and Shinkai S. Tetrahedron 63 (2007) 7326-7333