Bis(Amino Acid) oxalyl amides as ambidextrous gelators of water and organic solvents: Supramolecular gels with temperature dependent assembly/dissolution equilibrium

Chemistry - A European Journal

Volumn 7, Issue 15, 2001, Pages 3328-3341

  Makarević, Janja ^a   Jokić, Milan ^a   Perić, Berislav ^a   Tomišić, Vladislav ^b   Kojić Prodić, Biserka ^a   Žinić, Mladen ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Amides; Amino acids; Gels; NMR spectroscopy; Supramolecular chemistry

Indexed keywords

DISSOLUTION; GELS; MOLECULAR WEIGHT; ORGANIC SOLVENTS; SPECTROSCOPY; WATER;

INTERACTIONS;

SUPRAMOLECULAR CHEMISTRY;

ALCOHOL DERIVATIVE; AMIDE; AMINO ACID DERIVATIVE; DIMETHYL SULFOXIDE; N,N DIMETHYLFORMAMIDE; N,N' OXALYLBIS(LEUCINAMIDE); N,N' OXALYLBIS(PHENYLGLYCINAMIDE); N,N' OXALYLBIS(VALINAMIDE); ORGANIC SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CRYSTAL STRUCTURE; DIELECTRIC CONSTANT; DISSOLUTION; GEL; HYDROGEN BOND; INFRARED SPECTROSCOPY; LIPOPHILICITY; MELTING POINT; MOLECULAR INTERACTION; MOLECULAR MODEL; MOLECULAR WEIGHT; PROTON NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; TEMPERATURE DEPENDENCE; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0035800495     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010803)7:15<3328::AID-CHEM3328>3.0.CO;2-C     Document Type: Article

References (68)

1. J.-M. Lehn, Supramolecular Chemistry. Concepts and perspectives, VCH, Weinheim, 1995.
2. a) D. Venkataraman, S. Lee, J. Zhang, J. S. Moore, Nature 1994, 371, 591-593;
3. b) G. R. Desiraju, Crystal Engineering. The Design of Organic Solids, Elsevier, Amsterdam, 1989.
4. J.-H. Furhop, Membranes and Molecular Assemblies: the Synkinetic Approach, RSC Monographs in Supramolecular Chemistry (Ed.: J. Fraser Stoddart), 1994.
5. Some recent examples on small organic gelators include the following: a) P. Terech, Ber. Bunsenges. Phys. Chem. 1998, 102, 1630-1643;
6. b) P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133-3159;
7. c) K. Yoza, N. Amanokura, Y. Ono, T. Akao, H. Shinomori, M. Takeuchi, S. Shinkai, D. N. Reinhoudt, Chem. Eur. J. 1999, 5, 2722-2729;
8. d) R. Oda, I. Huc, S. J. Candau, Angew. Chem. 1998, 110, 2853-2858;
9. Angew. Chem. Int. Ed. 1998, 37, 2689-2691;
10. e) T. Kato, G. Kondo, K. Hanabusa Chem. Lett. 1988, 193-194;
11. f) J. van Esch, S. De Feyter, R. M. Kellog, F. DeSchryver, B. L. Feringa, Chem. Eur. J. 1997, 3, 1238-1243;
12. g) J.-E. S. Sohna, F. Fages, Chem. Commun. 1997, 327-328;
13. h) F. Placin, M. Colomes, J.-P. Desvergne, Tetrahedron Lett. 1997, 38, 2665-2668.
14. a) K. Murata, M. Aoki, T. Suzuki, T. Harda, H. Kawabata, T. Komori, F. Ohseto, K. Ukeda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676,
15. b) R. Mukkamala, R. G. Weiss, Langmuir 1996, 12, 1474-1482;
16. c) P. Terech, I. Furman, R. G. Weiss, H. Bouas-Laurent, J. P. Desvergne, R. Ramasseul, Faraday Discuss. 1995, 101, 345-358;
17. d) S. W. Jeong, S. Shinkai, Nanotechnology 1997, 8, 179-185;
18. e) Y. Hishikawa, K. Sada, R. Watanabe, M. Miyata, K. Hanabusa, Chem. Lett. 1998, 795-796.
19. a) T. Brotin, R. Utermöhlen, F. Fages, H. Bouas-Laurent, J.-P. Desvergne, J. Chem. Soc. Chem. Commun. 1991, 416-418;
20. b) J. L. Pozzo, G. M. Clavier, M. Colomes, H. Bouas-Laurent, Tetrahedron 1997, 55, 6377-6390.
21. P. Terech, V. Rodriguez, J. D. Barnes, G. B. McKenna, Langmuir 1994, 10, 3406-3418.
22. a) N. Mizoshita, T. Kutsuna, K. Hanabusa, T. Kato, J. Chem. Soc. Chem. Commun. 1999, 781-782;
23. b) K. Hanabusa, K. Okui, K. Karaki, M. Kimura, H. Shirai, J. Colloid Interface Sci. 1997, 195, 86-93;
24. c) K. Hanabusa, R. Tanaka, M. Suzuki, M. Kimura, H. Shirai, Adv. Mater. 1997, 9, 1095-1097;
25. d) F. Menger, Y. Yamasaki, K. K. Catlin, T. Nishimi, Angew. Chem. 1995, 107, 616-618;
26. Angew. Chem. Int. Ed. Engl. 1995, 34, 585-586;
27. e) T. T. Stock, N. J. Turner, R. McCague, J. Chem. Soc. Chem. Commun. 1995, 2063-2064;
28. f) E. J. de Vries, R. M. Kellog, J. Chem. Soc. Chem. Commun. 1993, 238-240.
29. Urea-based gelators: a) see [4f];
30. b) A. J. Carr, R. Melendez, S. J. Geib, A. D. Hamilton, Tetrahedron Lett. 1998, 39, 7447-7450;
31. sugar-based gelators: c) see [4c];
32. d) N. Amanokura, K. Yoza, H. Shinomori, S. Shinkai, D. N. Reinhoudt, J. Chem. Soc. Perkin Trans. 2 1998, 2585-2591;
33. e) K. Inoue, Y. Ono, Y. Kanekiyo, S. Kiyonaka, I. Hamachi, S. Shinkai, Chem. Lett. 1999, 225-226;
34. f) J.-H. Fuhrhop, S. Svenson, C. Boettcher, E. Rössler, H.-M. Vieth, J. Am. Chem. Soc. 1990, 112, 4307-4312;
35. g) T. Shimizu, M. Masuda, J. Am. Chem. Soc. 1997, 119, 2812-2818;
36. cyclohexyl amide derivatives: h) see [4e];
37. arylcyclohexanol derivatives: i) C. M. Garner, P. Terech, J.-J. Allegraud, B. Mistrot, P. Nguyen, A. de Geyer, D. Rivera, J. Chem. Soc. Faraday Trans. 1998, 94, 2173 -2179.
38. M. Jokić, J. Makarević, M. Žinić, J. Chem. Soc. Chem. Commun. 1995, 1723-1724.
39. a) J. Dong, Y. Ozaki, K. Nakashima, Macromolecules 1997, 30, 1111-1117;
40. b) L. Sun, L. J. Kepley, R. M. Crooks, Langmuir 1992, 8, 2101-2103.
41. 1H NMR study of the cholesterol/ stilbene gel appeared (D. C. Duncan, D. G. Whitten Langmuir 2000, 16, 6445-6452) providing the evidence that the gelator molecules dissolved in the gel liquid and those assembled in the mobile (NMR detectable) gel solid can be detected in the spectrum of a gel in a fast exchange on the NMR time scale. These NMR detectable gelator molecules are in the slow exchange with the solid (NMR undetectable) gel network.
42. -1 and the ΔH values appeared independent on the type of a solvent.
43. G. M. Clavier, J.-F. Brugger, H. Bouas-Laurent, J.-L. Pozzo, J. Chem. Soc. Perkin Trans. 2 1998, 2527-2534.
44. J. E. Eldridge, J. D. Ferry, J. Phys. Chem. 1954, 58, 992-996.
45. IUPAC-IUB Commission on Biochemical Nomenclature, J. Mol. Biol. 1970, 52, 1-17.
46. I. L. Karle, D. Ranghanathan, K. Shah, N. K. Vaish, Int. J. Peptide Protein Res. 1994, 43, 160-165.
47. I. L. Karle, D. Ranghanathan, Int. J. Peptide Protein Res. 1995, 46, 18-23.
48. I. L. Karle, D. Ranghanathan, Biopolymers 1995, 36, 323-331.
49. J. Bernstein, R. E. Davies, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1689-1708;
50. Angew. Chem. Int. Ed. Engl. 1995, 34, 1555-1573.
51. S. Coe, J. J. Kane, T. L. Nguyen, L. M. Toledo, E. Winiger, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 1997, 119, 86-93.
52. H.-J. Schneider, A. Yatsimirsky, Principles and Methods in Supramolecular Chemistry, Wiley, Chichester, 2000;
53. H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1439;
54. Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436.
55. X.-K. Jiang, G.-Z. Ji, B. Tu, X.-Y. Zhang, J.-L. Shi, X. Chen, J. Am. Chem. Soc. 1995, 117, 12679-12682.
56. D. J. Abdallah, R.-G. Weiss, Langmuir 2000, 16, 351-355.
57. S. Mann, Angew. Chem. 2000, 112, 3532-3548;
58. Angew. Chem. Int. Ed. 2000, 39, 3392-3406.
59. R. J. Bergeron, G. W. Yao, G. W. Erdos, S. Milstein, F. Gao, W. R. Weimar, O. Phanstiel, J. Am. Chem. Soc. 1995, 117, 6658-6665.
60. M. Akazome, T. Takahashi, K. Ogura, Tetrahedron Lett. 1998, 39, 4839-4842.
61. B. K. Vriesema, M. Lemaire, J. Buter, R. M. Kellogg, J. Org. Chem. 1986, 51, 5169-5177.
62. L. Karle, D. Ranganathan, K. Shah and N. K. Vaishi, Int. J. Peptide Protein Res. 1994, 43, 160-165.
63. A. G. Talma, P. Jouin, J. G. De Vries, C. B. Troostwijk, G. H. W. Buning, J. K. Waninge, J. Visscher, R. M. Kellogg, J. Am. Chem. Soc. 1985, 107, 3981-3997.
64. A. L. Spek, HELENA, Program for Data Reduction, 1993, University of Utrecht, Utrecht (The Netherlands).
65. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giaccovazzo, A. Guagliardi, G. Polidori, J. Appl. Crystallogr. 1994, 27, 435-436.
66. G. M. Sheldrick, SHELX97: Program for the Refinement of Crystal Structures, 1997, Universität of Göttingen (Germany).
67. A. L. Spek, PLATON98: A Multipurpose Crystallographic Tool, 120 398 Version, 1998, University of Utrecht, Utrecht (The Netherlands).
68. C. K. Johnson, ORTEPH, Report ORNL-5138, 1996, Oak Ridge National Laboratory, Tennessee.