Reversible transformation between rings and coils in a dynamic hydrogen-bonded self-assembly

Journal of the American Chemical Society

Volumn 131, Issue 15, 2009, Pages 5408-5410

  Yagai, Shiki ^a,b   Kubota, Shun ^a   Saito, Hikaru ^a   Unoike, Kanako ^a   Karatsu, Takashi ^a   Kitamura, Akihide ^a   Ajayaghosh, Ayyappanpillai ^c   Kanesato, Masatoshi ^d   Kikkawa, Yoshihiro ^d  

^a CHIBA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c REGIONAL RESEARCH LABORATORY CSIR   (India)

^d NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC SOLVENTS; BARBITURIC ACID; BIOLOGICAL ASSEMBLY; CHEMICAL STIMULI; FUNCTIONALIZED; HELICAL NANOSTRUCTURES; HYDROGEN BONDINGS; MOLECULAR BUILDING BLOCKS; OLIGO(P-PHENYLENEVINYLENE); QUASI-ONE-DIMENSIONAL; REVERSIBLE TRANSFORMATION; SELF-ORGANIZATION PROCESS; STACKING INTERACTION; TOBACCO MOSAIC VIRUS COAT PROTEIN;

HYDROGEN; NANOSTRUCTURED MATERIALS;

NANORINGS;

ALIPHATIC COMPOUND; NANOMATERIAL; BARBITURIC ACID; BARBITURIC ACID DERIVATIVE; BETA PROTEIN, BACTERIOPHAGE LAMBDA; CAPSID PROTEIN; DNA BINDING PROTEIN; H PROTEIN, TOBACCO MOSAIC VIRUS; OLIGO(P PHENYLENE VINYLENE); OLIGO(P-PHENYLENE VINYLENE); POLYVINYL DERIVATIVE; PROTEIN; SOLVENT; VIRUS PROTEIN;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; MOLECULE; MORPHOLOGY; NANOFABRICATION; SURFACE PROPERTY; BIOMIMETICS; CHEMISTRY; PHASE TRANSITION; PROTEIN CONFORMATION;

BARBITURATES; BIOMIMETICS; CAPSID PROTEINS; DNA-BINDING PROTEINS; HYDROGEN BONDING; NANOSTRUCTURES; PHASE TRANSITION; POLYVINYLS; PROTEIN CONFORMATION; PROTEINS; SOLVENTS; VIRAL PROTEINS;

EID: 67849092528     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9005892     Document Type: Article

References (40)

1. Klug, A. Angew. Chem. 1983, 95, 579-596.
2. Passy, S. I.; Yu, X.; Li, Z.; Radding, C. M.; Egelman, E. H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 4279-4284.
3. (a) Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644-656.
4. (b) Ajayaghosh, A.; Chithra, P.; Varghese, R. Angew. Chem., Int. Ed. 2007, 46, 230-233.
5. (c) Ryu, J.-H.; Kim, H.-J.; Huang, Z.; Lee, E.; Lee, M. Angew. Chem., Int. Ed. 2006, 45, 5304-5307.
6. (d) Nakanishi, T.; Schmitt, W.; Michinobu, T.; Kurth, D. G.; Ariga, K. Chem. Commun. 2005, 5982-5984.
7. Whitesides, G. M.; Grzybowski, B. Science 2002, 295, 2418-2421.
8. (a) Pochan, D. J.; Chen, Z.; Cui, H.; Hales, K.; Qi, K.; Wooley, K. L. Science 2004, 306, 94-97.
9. (b) Zhu, J.; Liao, Y.; Jiang, W. Langmuir 2004, 20, 3809-3812.
10. Kim, J.-K.; Lee, E.; Huang, Z.; Lee, M. J. Am. Chem. Soc. 2006, 128, 14022-14023.
11. Carlson, J. C. T.; Jena, S. S.; Flenniken, M.; Chou, T.-f.; Siegel, R. A.; Wagner, C. R. J. Am. Chem. Soc. 2006, 128, 7630-7638.
12. Lu, W.; Chui, S. S.-Y.; Ng, K.-M.; Che, C.-M. Angew. Chem., Int. Ed. 2008, 47, 4568-4572.
13. Yagai, S.; Mahesh, S.; Kikkawa, Y.; Unoike, K.; Karatsu, T.; Kitamura, A.; Ajayaghosh, A. Angew. Chem., Int. Ed. 2008, 47, 4691-4694.
14. For a review of other ring-shaped nanostructures, see: Vossmeyer, T.; Chung, S.-W.; Gelbart, W. M.; Heath, J. R. Adv. Mater. 1998, 10, 351-353.
15. For an example of concentration-driven transformation of nanostructures, see: Ajayaghosh, A.; Varghese, R.; Praveen, V. K.; Mahesh, S. Angew. Chem., Int. Ed. 2006, 45, 3261-3264.
16. For synthesis and characterization details, see the Supporting Information.
17. Selected examples of self-assembling OPVs: (a) Ajayaghosh, A.; George, S. J. J. Am. Chem. Soc. 2001, 123, 5148-5149.
18. (b) Jonkheijm, P.; Miura, A.; Zdanowska, M.; Hoeben, F. J. M.; De Feyter, S.; Schenning, A. P. H. J.; De Schryver, F. C.; Meijer, E. W. Angew. Chem., Int. Ed. 2004, 43, 74-78.
19. (c) Messmore, B. W.; Hulvat, J. F.; Sone, E. D.; Stupp, S. I. J. Am. Chem. Soc. 2004, 126, 14452-14458.
20. (d) Tomovic, Z.; van Dongen, J.; George, S. J.; Xu, H.; Pisula, W.; Leclere, P.; Smulders, M. M.; De Feyter, S.; Meijer, E. W.; Schenning, A. P. H. J. J. Am. Chem. Soc. 2007, 129, 16190-16196.
21. (e) Yagai, S.; Kubota, S.; Iwashima, T.; Kishikawa, K.; Nakanishi, T.; Karatsu, T.; Kitamura, A. Chem.-Eur. J. 2008, 14, 5246-5257.
22. Beginn, U.; Keinath, S.; Möller, M. Liq. Cryst. 1997, 23, 35-41.
23. These were the values after reducing the tip broadening factor (see Supporting Information for details).
24. Schenning, A. P. H. J.; Benneker, F. B. G.; Geurts, H. P. M.; Liu, X. Y.; Nolte, R. J. M. J. Am. Chem. Soc. 1996, 118, 8549-8552.
25. A barbituric acid derivative has been reported to form spiral nanostructures in an LB film: Huang, X.; Li, C.; Jiang, S.; Wang, X.; Zhang, B.; Liu, M. J. Am. Chem. Soc. 2004, 126, 1322-1323.
26. ten Cate, A. T.; Sijbesma, R. P. Macromol. Rapid Commun. 2002, 23, 1094-1112.
27. For reviews, see: (a) Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
28. (b) Zhao, D.; Moore, J. S. Org. Biomol. Chem. 2003, 1, 3471-3491.
29. Examples of self-assembled nanocoils formed by π-conjugated molecules: (a) Lovinger, A. J.; Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 264-268.
30. (b) Engelkamp, H.; Middelbeek, S.; Nolte, R. J. M. Science 1999, 284, 785-788.
31. (c) Hill, J. P.; Jin, W.; Kosaka, A.; Fukushima, T.; Ichihara, H; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. Science 2004, 304, 1481-1483.
32. (d) Ajayaghosh, A.; Vijayakumar, C.; Varghese, R.; George, S. J. Angew. Chem., Int. Ed. 2006, 45, 456-460.
33. (e) Yang, W.-Y.; Lee, E.; Lee, M. J. Am. Chem. Soc. 2006, 128, 3484-3485.
34. MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
35. (a) Cleverley, B.; Williams, P. P. Tetrahedron 1959, 7, 277-288.
36. (b) Craven, B. M.; Vizzini, E. A.; Rodrigues, M. M. Acta Crystallogr. 1969, B25, 1978-1993.
37. (a) Jin, S.; Ma, Y.; Zimmerman, S. C.; Cheng, S. Z. D. Chem. Mater. 2004, 16, 2975-2977.
38. (b) Yagai, S.; Nakajima, T.; Kishikawa, K.; Kohmoto, S.; Karatsu, T.; Kitamura, A. J. Am. Chem. Soc. 2005, 127, 11134-11139.
39. Zubarev, E. R.; Sone, E. D.; Stupp, S. I. Chem.-Eur. J. 2006, 12, 7313-7327.
40. Yagai, S.; Kinoshita, T.; Higashi, M.; Kishikawa, K.; Nakanishi, T.; Karatsu, T.; Kitamura, A. J. Am. Chem. Soc. 2007, 129, 13277-13287.