Self-assembly of bisurea compounds in organic solvents and on solid substrates

Chemistry - A European Journal

Volumn 3, Issue 8, 1997, Pages 1238-1243

  Van Esch, Jan ^a   De Feyter, Steven ^b   Kellogg, Richard M ^a   De Schryver, Frans ^b   Feringa, Ben L ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Electron microscopy; Gels; Scanning tunneling microscopy; Self assembly; Ureas

Indexed keywords

EID: 0030794767     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030811     Document Type: Article

References (45)

1. For an excellent review see: D. Philp, J. F. Stoddart, Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
2. G. S. Hanan, C. R. Arana, J. M. Lehn, D. Fenske, Angew. Chem. Int. Ed. Engl. 1995, 34, 1122-1124; J. F. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, J. Am. Chem. Soc. 1996, 118, 43-50; J. Sartorius, H. J. Schneider, Chem. Eur. J. 1996, 2, 1446-1452; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. Int. Ed. Engl. 1996, 35, 2204-2206.
3. G. S. Hanan, C. R. Arana, J. M. Lehn, D. Fenske, Angew. Chem. Int. Ed. Engl. 1995, 34, 1122-1124; J. F. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, J. Am. Chem. Soc. 1996, 118, 43-50; J. Sartorius, H. J. Schneider, Chem. Eur. J. 1996, 2, 1446-1452; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. Int. Ed. Engl. 1996, 35, 2204-2206.
4. G. S. Hanan, C. R. Arana, J. M. Lehn, D. Fenske, Angew. Chem. Int. Ed. Engl. 1995, 34, 1122-1124; J. F. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, J. Am. Chem. Soc. 1996, 118, 43-50; J. Sartorius, H. J. Schneider, Chem. Eur. J. 1996, 2, 1446-1452; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. Int. Ed. Engl. 1996, 35, 2204-2206.
5. G. S. Hanan, C. R. Arana, J. M. Lehn, D. Fenske, Angew. Chem. Int. Ed. Engl. 1995, 34, 1122-1124; J. F. Hartgerink, J. R. Granja, R. A. Milligan, M. R. Ghadiri, J. Am. Chem. Soc. 1996, 118, 43-50; J. Sartorius, H. J. Schneider, Chem. Eur. J. 1996, 2, 1446-1452; M. Mascal, N. M. Hext, R. Warmuth, M. H. Moore, J. P. Turkenburg, Angew. Chem. Int. Ed. Engl. 1996, 35, 2204-2206.
6. J. H. Fuhrhop, J. Köning, Membranes and Molecular Assemblies: The Synkinetic Approach, Royal Society of Chemistry, Cambridge, 1994; J. M. Lehn, Supramolecular chemistry, VCH, Weinheim, 1995.
7. J. H. Fuhrhop, J. Köning, Membranes and Molecular Assemblies: The Synkinetic Approach, Royal Society of Chemistry, Cambridge, 1994; J. M. Lehn, Supramolecular chemistry, VCH, Weinheim, 1995.
8. E. J. de Vries, R. M. Kellogg, J. Chem. Soc. Chem. Commun. 1993, 238-240; C. S. Snijder, J. C. de Jong, A. Meetsma, F. van Bolhuis, B. L. Feringa, Chem. Eur. J. 1995, 1, 594-597.
9. E. J. de Vries, R. M. Kellogg, J. Chem. Soc. Chem. Commun. 1993, 238-240; C. S. Snijder, J. C. de Jong, A. Meetsma, F. van Bolhuis, B. L. Feringa, Chem. Eur. J. 1995, 1, 594-597.
10. R. J. Twieg, T. P. Russell, R. S. Siemens, J. F. Rabolt, Macromolecules 1985, 18, 1361-1362; K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676; P. Terech, I. Furman, R. G. Weiss, J. Phys. Chem. 1995, 99, 9558-9566; P. Terech, in Specialist Surfactants (Ed.: I. D. Robb), Chapmann and Hall, 1997.
11. R. J. Twieg, T. P. Russell, R. S. Siemens, J. F. Rabolt, Macromolecules 1985, 18, 1361-1362; K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676; P. Terech, I. Furman, R. G. Weiss, J. Phys. Chem. 1995, 99, 9558-9566; P. Terech, in Specialist Surfactants (Ed.: I. D. Robb), Chapmann and Hall, 1997.
12. R. J. Twieg, T. P. Russell, R. S. Siemens, J. F. Rabolt, Macromolecules 1985, 18, 1361-1362; K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676; P. Terech, I. Furman, R. G. Weiss, J. Phys. Chem. 1995, 99, 9558-9566; P. Terech, in Specialist Surfactants (Ed.: I. D. Robb), Chapmann and Hall, 1997.
13. R. J. Twieg, T. P. Russell, R. S. Siemens, J. F. Rabolt, Macromolecules 1985, 18, 1361-1362; K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664-6676; P. Terech, I. Furman, R. G. Weiss, J. Phys. Chem. 1995, 99, 9558-9566; P. Terech, in Specialist Surfactants (Ed.: I. D. Robb), Chapmann and Hall, 1997.
14. K. Hanabusa, Y. Matsumoto, T. Miki, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1994, 1401-1402; K. Hanabusa, M. Yamada, M. Kimura, H. Shiray, Angew. Chem. Int. Ed. Engl. 1996, 35, 1949-1951.
15. K. Hanabusa, Y. Matsumoto, T. Miki, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1994, 1401-1402; K. Hanabusa, M. Yamada, M. Kimura, H. Shiray, Angew. Chem. Int. Ed. Engl. 1996, 35, 1949-1951.
16. Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauher, J. Am. Soc. Chem. 1993, 115, 5991-6000; G. R. Desiraju, Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
17. Y.-L. Chang, M.-A. West, F. W. Fowler, J. W. Lauher, J. Am. Soc. Chem. 1993, 115, 5991-6000; G. R. Desiraju, Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327.
18. K. Hanabusa, K. Shimura, K. Hirose, M. Kimura, H. Shirai, Chem. Lett. 1996, 885-886.
19. J. van Esch, R. M. Kellogg, B. L. Feringa, Tetrahedron Lett. 1997, 38, 281-284.
20. We thank one of the referees for bringing the early work of Campbell et al. to our attention: J. Campbell, M. Kuzma, M. M. Labes, Mol. Cryst. Liq. Cryst. 1983, 95, 45-50.
21. For this reason we chose some high-boiling organic solvents to investigate their ability to gelate organic solvents.
22. Y. Mido, Spectr. Chim. Acta 1972, 28A, 1503-1518.
23. Single fibers are best observed at the interfaces between gel and solvent.
24. Many other compounds also form fibers. See, for instance, for light microscopic observations: I. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 1985, 107, 509-510; and for electron microscopy: J. H. Fuhrhop, P. Schneider, E. Boekema, W. Helfrich, J. Am. Chem. Soc. 1988, 110, 2861-2867; Y. Ishikawa, H. Kuwahara, T. Kunitake, ibid. 1989, 111, 8530-8531; T. Imea, Y. Takahashi, H. Muramatsu, ibid. 1992, 114, 3414-3419.
25. Many other compounds also form fibers. See, for instance, for light microscopic observations: I. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 1985, 107, 509-510; and for electron microscopy: J. H. Fuhrhop, P. Schneider, E. Boekema, W. Helfrich, J. Am. Chem. Soc. 1988, 110, 2861-2867; Y. Ishikawa, H. Kuwahara, T. Kunitake, ibid. 1989, 111, 8530-8531; T. Imea, Y. Takahashi, H. Muramatsu, ibid. 1992, 114, 3414-3419.
26. Many other compounds also form fibers. See, for instance, for light microscopic observations: I. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 1985, 107, 509-510; and for electron microscopy: J. H. Fuhrhop, P. Schneider, E. Boekema, W. Helfrich, J. Am. Chem. Soc. 1988, 110, 2861-2867; Y. Ishikawa, H. Kuwahara, T. Kunitake, ibid. 1989, 111, 8530-8531; T. Imea, Y. Takahashi, H. Muramatsu, ibid. 1992, 114, 3414-3419.
27. Many other compounds also form fibers. See, for instance, for light microscopic observations: I. Nakashima, S. Asakuma, T. Kunitake, J. Am. Chem. Soc. 1985, 107, 509-510; and for electron microscopy: J. H. Fuhrhop, P. Schneider, E. Boekema, W. Helfrich, J. Am. Chem. Soc. 1988, 110, 2861-2867; Y. Ishikawa, H. Kuwahara, T. Kunitake, ibid. 1989, 111, 8530-8531; T. Imea, Y. Takahashi, H. Muramatsu, ibid. 1992, 114, 3414-3419.
28. J.-M. Guenet, Thermoreversible Gelation of Polymers and Biopolymers, Academic Press, London, 1992.
29. P. Hartman, P. Bennema, J. Cryst. Growth 1980, 49, 145-156; I. Weissbuch, R. Popovitz-Biro, M. Lahav, L. Leiserowitz, Acta Crystallogr. 1995, B51, 115-148.
30. P. Hartman, P. Bennema, J. Cryst. Growth 1980, 49, 145-156; I. Weissbuch, R. Popovitz-Biro, M. Lahav, L. Leiserowitz, Acta Crystallogr. 1995, B51, 115-148.
31. P. Terech, E. Ostuni, R. G. Weiss, J. Phys. Chem. 1996, 100, 3759-3766; E. Ostuni, P. Kamaras, R. G. Weiss, Angew. Chem. Int. Ed. Engl. 1996, 35, 1324-1326.
32. P. Terech, E. Ostuni, R. G. Weiss, J. Phys. Chem. 1996, 100, 3759-3766; E. Ostuni, P. Kamaras, R. G. Weiss, Angew. Chem. Int. Ed. Engl. 1996, 35, 1324-1326.
33. K. Fontell, Liquid Crystals and Plastic Crystals (Eds.: G. W. Gray, P. A. Windsor), John Wiley, London, 1974, Vol. 2, 80-109.
34. J. P. Rabe, Ultramicroscopy 1992, 42-44, 41-54; J. Frommer, Angew. Chem. Int. Ed. Engl. 1992, 31, 1298-1328; D. M. Cyr, B. Venkataraman, G. W. Flynn, Chem. Mater. 1996, 8, 1600-1615.
35. J. P. Rabe, Ultramicroscopy 1992, 42-44, 41-54; J. Frommer, Angew. Chem. Int. Ed. Engl. 1992, 31, 1298-1328; D. M. Cyr, B. Venkataraman, G. W. Flynn, Chem. Mater. 1996, 8, 1600-1615.
36. J. P. Rabe, Ultramicroscopy 1992, 42-44, 41-54; J. Frommer, Angew. Chem. Int. Ed. Engl. 1992, 31, 1298-1328; D. M. Cyr, B. Venkataraman, G. W. Flynn, Chem. Mater. 1996, 8, 1600-1615.
37. P. Vanoppen, P. C. M. Grim, M. Rücker, S. De Feyter, G. Moessner, S. Valiyaveettil, K. Müllen, F. C. De Schryver, J. Phys. Chem. in press.
38. In this paper the STM term "lamella" is replaced by "ribbon" in order to avoid interference with the X-ray terminology.
39. The intermolecular distance within one ribbon could be determined with high accuracy by making use of the Moiré pattern: A. Stabel, R. Heinz, J. P. Rabe, G. Wegner, F. C. De Schryver, D. Corens, W. Dehaen, C. Süling, J. Phys. Chem. 1995, 99, 8690-8697.
40. Examination of 28 crystal structures of noncyclic urea compounds deposited in the Cambridge Crystallographic Database revealed that the average distance between two successive hydrogen-bonded urea groups is 0.46 nm.
41. S. De Feyter, M. Ruecker, K. Grim, P. Vanoppen, J. van Esch, B. L. Feringa, R. M. Kellogg, F. De Schrijver, unpublished results.
42. F. Ania, D. R. Rueda, F. J. Balta Calleja, Makromol. Chem. 1981, 183, 235-239.
43. A Philipse, Langmuir 1996, 12, 1127-1133.
44. H. M. Tan, A. Moet, A. Hiltner, E. Baer, Macromolecules, 1983, 16, 28.
45. H. J. C. Berendsen, D. van der Spoel, R. van Drunen, Comp. Phys. Commun. 1995, 95, 43-56.