Dye-assisted structural modulation of hydrogen-bonded binary supramolecular polymers

Chemistry of Materials

Volumn 17, Issue 17, 2005, Pages 4392-4398

  Yagai, Shiki ^a   Higashi, Masatsugu ^a   Karatsu, Takashi ^a   Kitamura, Akihide ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DIMERS; DYES; HYDROGEN BONDS; MELAMINE; ORGANIC SOLVENTS; POLYMERIZATION; SCANNING ELECTRON MICROSCOPY; ULTRAVIOLET RADIATION;

BINARY SUPRAMOLECULAR POLYMERS; DIMERIC MELAMINE; STRUCTURAL MODULATION; SUPRAMOLECULAR POLYMERIZATION;

SUPRAMOLECULAR CHEMISTRY;

EID: 24944521646     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm0510413     Document Type: Article

References (57)

1. Dill, K. A. Biochemistry 1990, 29, 7133-7155.
2. (a) Muthukumar, M.; Ober, C. K.; Thomas, E. L. Science 1997, 277, 1225-1232.
3. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
4. (c) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
5. (d) Li, A. D. Q.; Wang, W.; Wang, L.-Q. Chem. - Eur. J. 2003, 9, 4594-4601.
6. (e) Huc, I. Eur. J. Org. Chem. 2004, 17-29.
7. (f) Lee, M.; Cho, B.-K.; Zin, W.-C. Chem. Rev. 2001, 101, 3869-3892.
8. (g) Klok, H.-A.; Lecommandoux, S. Adv. Mater. 2001, 13, 1217-1229.
9. (h) Ikkala, O.; ten Brinke, G. Chem. Commun. 2004, 2131-2137.
10. (a) Nguyen, J. Q.; Iverson, B. L. J. Am. Chem. Soc. 1999, 127, 2639-2640.
11. (b) Zhang, W.; Horoszewski, D.; Decatur, J.; Nuckolls, C. J. Am. Chem. Soc. 2003, 125, 4870-4873.
12. (c) Wang, W.; Li, L.-S.; Helms, G.; Zhou, H.-H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120-1121.
13. (d) Wang, W.; Wan, W.; Zhou, H.-H.; Niu, S.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 5248-5249.
14. (e) Ghosh, S.; Ramakrishnan, S. Angew. Chem., Int. Ed. 2004, 43, 3264-3268.
15. (a) Brunsveld, L.; Folmer, B. J. B.; Sijbesma, R. P.; Meijer, E. W. Chem. Rev. 2001, 101, 4071-4098.
16. (b) ten Cate, A. T.; Sijbesma, R. P. Macromol. Rapid Commun. 2002, 23, 1094-1112.
17. (c) Ciferri, A. Macromol. Rapid Commun. 2002, 23, 511-529.
18. (d) Lehn, J.-M. Polym. Int. 2002, 51, 825-839.
19. (a) Hirschberg, J. H. K.; Brunsveld, L.; Ramzi, A.; Vekemans, J. A. J. M.; Sijbesma, R. P.; Meijer, E. W. Nature 2000, 407, 167-170.
20. (b) Brunsveld, L.; Vekemans, J. A. J. M.; Hirschberg, J. H. K.; Sijbesma, R. P.; Meijer, E. W. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4977-4982.
21. (c) Hirschberg, J. H. K.; Koevoets, R. A.; Sijbesma, R. P.; Meijer, E. W. Chem. - Eur. J. 2003, 9, 4222-4231.
22. (a) Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546.
23. (b) Schoonbeek, F. S.; van Esch, J. H.; Wegewijs, B.; Rep, D. B. A.; de Haas, M. P.; Klapwijk, T. M.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 1999, 38, 1393-1397.
24. (c) Würthner, F.; Thalacker, C.; Sautter, A.; Schärtl, W.; Ibach, W.; Hollricher, O. Chem. - Eur. J. 2000, 6, 3871-3886.
25. (d) El-ghayoury, A.; Schenning, A. P. H. J.; van Hal, P. A.; van Duren, J. K. J.; Janssen, R. A. J.; Meijer, E. W. Angew. Chem., Int. Ed. 2001, 40, 3660-3663.
26. (e) Schenning, A. P. H. J.; Jonkheijm, P.; Peeters, E.; Meijer, E. W. J. Am. Chem. Soc. 2001, 123, 409-416.
27. (f) Ajayaghosh, A.; George, S. J.; Praveen, V. K. Angew. Chem., Int. Ed. 2003, 42, 332-335.
28. (g) Würthner, F.; Yao, S.; Beginn, U. Angew. Chem., Int. Ed. 2003, 42, 3247-3250.
29. (h) Hoeben, F. J. M.; Herz, L. M.; Daniel, C.; Jonkheijm, P.; Schenning, A. P. H. J.; Silva, C.; Meskers, S. C. J.; Beljonne, D.; Phillips, R. T.; Friend, R. H.; Meijer, E. W. Angew. Chem., Int. Ed. 2004, 43, 1976-1979.
30. (i) Sugiyasu, K.; Fujita, N.; Shinkai, S. Angew. Chem., Int. Ed. 2004, 43, 1229-1233.
31. (j) George, S. J.; Ajayaghosh, A.; Jonkheijm, P.; Schenning, A. P. H. J.; Meijer, E. W. Angew. Chem., Int. Ed. 2004, 43, 3422-3425.
32. (k) Würthner, F.; Chen, Z.; Hoeben, F. J. M.; Osswald, P.; You, C.-C.; Jonkheijm, P. Herrikhuyzen, J. v.; Schenning, A. P. H. J.; van der Schoot, P. P. A. M.; Meijer, E. W.; Beckers, E. H. A.; Meskers, S. C. J.; Janssen, R. A. J. J. Am. Chem. Soc. 2004, 126, 10611-10618.
33. (l) Messmore, B. W.; Hulvat, J. F.; Sone, E. D.; Stupp, S. I. J. Am. Chem. Soc. 2004, 126, 14452-14458.
34. Thalacker, C.; Miura, A.; De Feyter, S.; De Schryver, F. C.; Würthner, F. Org. Biomol. Chem. 2005, 3, 414-422.
35. (n) Ajayaghosh, A.; George, S. J. J. Am. Chem. Soc. 2001, 123, 5148-5149.
36. (o) Ajayaghosh, A.; George, S. J. Chem. -Eur. L 2005, 11, 3217-3227.
37. Yagai, S.; Higashi, M.; Karatsu, T.; Kitamura, A. Chem. Mater. 2004, 16, 3582-3585.
38. (a) Inoue, K.; Ono, Y.; Kanekiyo, Y.; Ishi-I, T.; Yoshihisa, K.; Shinkai, S. J. Org. Chem. 1999, 64, 2933-2937.
39. (b) Berl, V.; Krische, M. J.; Hue, I.; Lehn, J.-M.; Schmutz, M. Chem. - Eur. J. 2000, 6, 1938-1946.
40. (c) Ikeda, M.; Nobori, T.; Schmutz, M.; Lehn, J-.M. Chem. -Eur. J. 2005, 11, 662-668.
41. (a) Yang, W.; Jiang, Y.; Chai, X.; Li, T.; Fu, L.; Zhang, H. Sci. China 2000, 43, 555-560.
42. (b) Ahuja, R.; Caruso, P.-L.; Möbius, D.; Paulus, W.; Ringsdorf, H.; Wildburg, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1033-1036.
43. (c) Bohanon, T. M.; Caruso, P.-L.; Denzinger, S.; Fink, R.; Möbius, D.; Paulus, W.; Preece, J. A.; Ringsdorf, H.; Schollmeyer, D. Langmuir 1999, 15, 174-184.
44. (d) Huang, X.; Li, C.; Jiang, S.; Wang, X.; Zhang, B.; Liu, M. J. Am. Chem. Soc. 2004, 126, 1332-1323.
45. (e) Würthner, F.; Yao, S.; Heise, B.; Tschierske, C. Chem. Commun. 2001, 2260-2261.
46. The same sheetlike structure has been observed in weaker organogel systems: (a) Jung, J. H.; Ono, Y.; Shinkai, S. Langmuir 2000, 16, 1643-1649.
47. (b) Watanabe, Y.; Miyasou, T.; Hayashi, M. Org. Lett. 2004, 6, 1547-1550.
48. Wang, R.; Geiger, C.; Chen, L.; Swanson, B.; Whitten, D. G. J. Am. Chem. Soc. 2000, 122, 2399-2400.
49. Würthner, F.; Yao, S. J. Org. Chem. 2003, 68, 8943-8949.
50. Prins, L. J.; Thalacker, C.; Würthner, F.; Timmerman, P.; Reinhoudt, D. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4814-4817.
51. Würthner, F.; Yao, S.; Debaerdemaeker, T.; Wortmann, R. J. Am. Chem. Soc. 2002, 124, 9431-9447.
52. Shinkai et al. reported that J- and H-aggregates of the hydrogen-bonding porphyrin derivatives exhibit sheet and fiber superstructures, respectively: Shirakawa, M.; Kawano, S.; Fujita, N.; Sada, K.; Shinkai, S. J. Org. Chem. 2003, 68, 5037-5044.
53. Other supramolecular polymers of which secondary structures can be tunable by the second component: (a) Yamaguchi, T.; Ishii, N.; Tashiro, K.; Aida, T. J. Am. Chem. Soc. 2003, 125, 13934-13935.
54. (b) Kim, H.-J.; Zin, W.-C.; Lee, M. J. Am. Chem. Soc. 2004, 126, 7009-7014.
55. (c) Shirakawa, M.; Fujita, N.; Shinkai, S. J. Am. Chem. Soc. 2004, 126, 9902-9903.
56. (d) Hardy, J. G.; Hirst, A. R.; Smith, D. K.; Brennan, C.; Ashworth, I. Chem. Commun. 2005, 385-387.
57. (e) Hirst, A. R.; Smith, D. K.; Feiters, M. C.; Geurts, H. P. M.; Wright, A. C. J. Am. Chem. Soc. 2003, 125, 9010-9011.