Chiral molecular assemblies from a novel achiral amphiphilic 2-(heptadecyl) naphtha[2,3]imidazole through interfacial coordination

Journal of the American Chemical Society

Volumn 125, Issue 17, 2003, Pages 5051-5056

  Yuan, Jing ^a   Liu, Minghua ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

COORDINATION REACTIONS; INTERFACES (MATERIALS); MOLECULES; SYNTHESIS (CHEMICAL); WATER;

MOLECULAR ASSEMBLIES;

ORGANIC COMPOUNDS;

2 (HEPTADECYL)NAPHTHA[2,3]IMIDAZOLE; AMPHOPHILE; IMIDAZOLE DERIVATIVE; SILVER NITRATE; UNCLASSIFIED DRUG;

ADSORPTION; ARTICLE; ATOMIC FORCE MICROSCOPY; CHIRALITY; CIRCULAR DICHROISM; FILM; FOURIER TRANSFORMATION; INFRARED SPECTROSCOPY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0037473526     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0288486     Document Type: Article

References (43)

1. Oda, R.; Huc, I.; Schmutz, M.; Candau, S. J.; MacKintosh, F. C. Nature 1999, 399, 566.
2. Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 1998, 37, 63.
3. Stryer, L.; Blout, E. R. J. Am. Chem. Soc. 1961, 83, 1411.
4. Kawasaki, T.; Tokuhiro, M.; Kimizuka, N.; Kunitake, T. J. Am. Chem. Soc. 2001, 123, 6792.
5. (a) Bellacchio, E.; Lauceri, R.; Gurrieri, S.; Scolaro, L. M.; Romeo, A.; Purrello. R. J. Am. Chem. Soc. 1998, 120, 12353.
6. (b) Lauceri, R.; Raudino, A.; Scolaro, L. M.; Micali, N.; Purrello, R. J. Am. Chem. Soc. 2002, 124, 894.
7. Honda, C.; Hada, H. Tetahedron Lett. 1976, 3, 177.
8. Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449.
9. Link, D. R.; Natale, G.; Shao, R.; Maclennan, J. E.; Clark, N. A.; Körblova, E.; Walba, D. M. Science 1997, 278, 1924.
10. Ribó, J. M.; Crusats, J.; Sagués, F.; Claret, J.; Rubires, R. Science 2001, 292, 2063.
11. Dantlgraber, G.; Eremin, A.; Diele, S.; Hauser, A.; Kresse, H.; Pelzl, G.; Tschierske, C. Angew. Chem., Int. Ed. 2002, 41, 2408.
12. (a) Spitz, C.; Dähne, S.; Ouart, A.; Abraham, H. W. J. Phys. Chem. B 2000, 104, 8664-8669.
13. (b) Rossi, U. D.; Dähne, S.; Meskers, S. C. J.; Dekkers, H. P. J. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 760.
14. Yang, W. S.; Chai, X. D.; Chi, L. F.; Liu, X. D.; Cao, Y. W.; Lu, R.; Jiang, Y. S.; Tang, X. Y.; Fuchs, H.; Li, T. Chem.-Eur. J. 1999, 5, 1144.
15. Gaines, G. L., Jr. Insoluble Monolayers at Liquid-Gas Interfaces; Interscience: New York, 1966.
16. Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: Boston, MA, 1991.
17. Nuckolls, C.; Katz, T. J.; Verbiest, T.; Elshocht, S. V.; Kuball, H. G.; Kiesewalter, S.; Lovinger, A. J.; Persoons, A. J. Am. Chem. Soc. 1998, 120, 8656.
18. (a) Arnett, E. M.; Harvey, N. G.: Rose, P. L. Acc. Chem. Res. 1989, 22, 131.
19. (b) Harvey, N. G.; Mirajovsky, D.; Rose, P. L.; Verbiar, R.; Arnett, E. M. J. Am. Chem. Soc. 1989, 111, 1115.
20. (c) Heath, J. G.; Arnett, E. M. J. Am. Chem. Soc. 1992, 114, 4500.
21. Pathirana, S.; Neely, W. C.; Myers, L. J.; Vodyanoy, V. J. Am. Chem. Soc. 1992, 114, 1404-1405.
22. Feng, F.: Miyashita, T.; Okubo, H.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10166.
23. (a) Liu, M. H.; Kira, A.; Nakahara, H. Langmuir 1997, 13, 4807-4809.
24. (b) Gong, H. F.; Liu, M. H. Langmuir 2001, 17, 6228-6232.
25. (c) Liu, M. H.; Xu, G.; Liu, Y. H.; Chen, Q. Langmuir 2001, 17, 427.
26. (a) Seka, R.; Müller, R. H. Monatsh. Chem. 1931, 57, 95.
27. (b) Pool, W. O.; Harwood, H. J.; Ralston, A. W. J. Am. Chem. Soc. 1937, 59, 178.
28. (a) Dik-Edixhoven, C. J.; Schenk, H.; Van der Meer, H. Crystallogr. Struct. Commun. 1973, 2, 23.
29. (b) Escande, A.; Galign, J. L. Acta Crystallogr. 1974, B30, 1647.
30. (a) Shanon, R. D.: Prewitt, C. T. Acta Crystallogr. 1969, B25, 925.
31. (b) Shanon, R. D. Acta Crystallogr. 1976, A32, 751.
32. Koltun, W. L. Precision Space-Filling Atomic Models Biopolymers 3 1965, 665.
33. Kuzmenko, I.; Rapaport, H.; Kjaer, K.; Als-Nielsen, J.; Weissbuch, I.; Lahav, M.; Leiserowitz, L. Chem. Rev. 2001, 101, 1659-1696.
34. Xue, G.; Dai, Q.; Jiang S. J. Am. Chem. Soc. 1988, 110, 2393.
35. Kuroda, R.; Harada, T.; Shindo, Y. Rev. Sci. Instrum. 2001, 72, 3802.
36. (a) Kuball, H. G.; Höfer, T. Chirality 2000, 12, 278.
37. (b) Frelek, J.; Szczepek, W. J.; Neubrech, S.: Schultheis, B.; Brechtel, J.; Kuball, H. G. Chem.-Eur. J. 2002, 8, 1899.
38. Saeva, F. D.; Olin, G. R. J. Am. Chem. Soc. 1977, 99, 4848.
39. It should be noted that during the progress of the reaction, the UV absorption maximum shifted from 245 to 240 and to a final 230 nm.
40. Circular Dichroism Principles and Applications, 2nd ed.; Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: New York, 2000.
41. Cintas, P. Angew. Chem., Int. Ed. 2002, 41, 1139.
42. Huang, X.; Liu, M. H. Chem. Commun. 2003, 66.
43. Gold, D. H.; Gregor, H. P. J. Phys. Chem. 1960, 64, 1461.