Topochemical polymerization in supramolecular polymers of oligopeptide-functionalized diacetylenes

Angewandte Chemie - International Edition

Volumn 45, Issue 32, 2006, Pages 5383-5386

  Jahnke, Eike ^a   Lieberwirth, Ingo ^b   Severin, Nikolai ^c   Rabe, Jürgen P ^c   Frauenrath, Holger ^a  

^a ETH ZURICH   (Switzerland)

^b MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^c HUMBOLDT UNIVERSITY   (Germany)

Author keywords

sheets; Double helix; Hierarchical structures; Self assembly; Topochemical polymerization

Indexed keywords

DOUBLE HELIX; HIERARCHICAL STRUCTURES; TOPOCHEMICAL POLYMERIZATION;

AMINO ACIDS; BIOCHEMISTRY; POLYMERIZATION; POLYMERS; SUPRAMOLECULAR CHEMISTRY;

ACETYLENE;

ALKYNE; OLIGOPEPTIDE; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

ALKYNES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OLIGOPEPTIDES; POLYMERS;

EID: 33747874788     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200600610     Document Type: Article

References (55)

1. a) M. Muthukumar, C. K. Ober, E. L. Thomas, Science 1997, 277, 1225;
2. b) R. Lakes, Nature 1993, 361, 511.
3. a) J.-M. Lehn, Science 2002, 295, 2400;
4. b) G. M. Whitesides, B. Grzybowski, Science 2002, 295, 2418.
5. D. J. Selkoe, Nature 2003, 426, 900.
6. a) O. S. Makin, L. C. Serpell, J. Mol. Biol. 2004, 335, 1279;
7. b) M. Sunde, L. C. Serpell, M. Bartlam, P. E. Fraser, M. B. Pepys, C. C. F. Blake, J. Mol. Biol. 1997, 273, 729;
8. c) J. P. Bond, S. P. Deverin, H. Inouye, O. M. A. El-Agnaf, M. M. Teeter, D. A. Kirschner, J. Struct. Biol. 2003, 141, 156;
9. d) C. Goldsbury, P. Frey, V. Olivieri, U. Aebi, S. A. Müller, J. Mol. Biol. 2005, 352, 282;
10. e) C. Goldsbury, J. Kistler, U. Aebi, T. Arvinte, G. J. S. Cooper, J. Mol. Biol. 1999, 285, 33.
11. a) A. Aggeli, M. Bell, N. Boden, J. N. Keen, P. F. Knowles, T. C. McLeish, M. Pitkeathly, S. E. Radford, Nature 1997, 386, 259;
12. b) C. Whitehouse, J. Fang, A. Aggeli, M. Bell, R. Brydson, C. W. G. Fishwick, J. R. Henderson, C. M. Knobler, R. W. Owens, N. H. Thomson, D. A. Smith, N. Boden, Angew. Chem. 2005, 117, 2001;
13. Angew. Chem. Int. Ed. 2005, 44, 1965.
14. H. A. Lashuel, S. R. LaBrenz, L. Woo, L. C. Serpell, J. W. Kelly, J. Am. Chem. Soc. 2000, 122, 5262.
15. a) J. M. Smeenk, M. B. J. Otten, J. Thies, D. A. Tirrell, H. G. Stunnenberg, J. C. M. van Hest, Angew. Chem. 2005, 117, 2004;
16. Angew. Chem. Int. Ed. 2005, 44, 1968;
17. b) J. H. Collier, P. B. Messersmith, Adv. Mater. 2004, 16, 907;
18. c) T. S. Burkoth, T. L. S. Benzinger, D. N. M. Jones, K. Hallenga, S. C. Meredith, D. G. Lynn, J. Am. Chem. Soc. 1998, 120, 7655;
19. d) T. S. Burkoth, T. L. S. Benzinger, V. Urban, D. G. Lynn, S. C. Meredith, P. Thiyagarajan, J. Am. Chem. Soc. 1999, 121, 7429.
20. a) O. Rathore, D. Y. Sogah, J. Am. Chem. Soc. 2001, 123, 5231;
21. b) O. Rathore, D. Y. Sogah, Macromolecules 2001, 34, 1477;
22. c) J. Yao, D. Xiao, X. Chen, P. Zhou, T. Yu, Z. Shao, Macromolecules 2003, 36, 7508.
23. T. Scheibel, R. Parthasarathy, G. Sawicki, X.-M. Lin, H. Jaeger, S. L. Lindquist, Proc. Natl. Acad. Sci. USA 2003, 100, 4527.
24. a) G. Wegner, Z. Naturforsch. B 1969, 24, 824;
25. b) G. Wegner, Makromol. Chem. 1972, 154, 35.
26. a) B. Tieke, G. Wegner, D. Naegele, H. Ringsdorf, Angew. Chem. 1976, 88, 805;
27. Angew. Chem. Int. Ed. Engl. 1976, 15, 764;
28. b) D. N. Batchelder, S. D. Evans, T. L. Freeman, L. Haeussling, H. Ringsdorf, H. Wolf, J. Am. Chem. Soc. 1994, 116, 1050;
29. c) K. Kuriyama, H. Kikuchi, T. Kajiyama, Langmuir 1996, 12, 2283;
30. d) K. E. Muggins, S. Son, S. I. Stupp, Macromolecules 1997, 30, 5305;
31. e) D. W. Britt, U. G. Hofmann, D. Moebius, S. W. Hell, Langmuir 2001, 17, 3757.
32. a) Y. Okawa, M. Aono, Nature 2001, 409, 683;
33. b) A. Miura, S. De Feyter, M. M. S. Abdel-Mottaleb, A. Gesquiere, P. C. M. Grim, G. Moessner, M. Sieffert, M. Klapper, K. Müllen, F. C. De Schryver, Langmuir 2003, 19, 6474;
34. c) S. P. Sullivan, A. Schnieders, S. K. Mbugua, T. P. Beebe, Langmuir 2005, 21, 1322.
35. a) J. H. Georger, A. Singh, R. R. Price, J. M. Schnur, P. Yager, P. E. Schoen, J. Am. Chem. Soc. 1987, 109, 6169;
36. b) A. Singh, E. M. Wong, J. M. Schnur, Langmuir 2003, 19, 1888;
37. c) S. Svenson, P. B. Messersmith, Langmuir 1999, 15, 4464;
38. d) Q. Cheng, M. Yamamoto, R. C. Stevens, Langmuir 2000, 16, 5333;
39. e) D. A. Frankel, D. F. O'Brien, J. Am. Chem. Soc. 1991, 113, 7436;
40. f) J. H. Fuhrhop, P. Blumtritt, C. Lehmann, P. Luger, J. Am. Chem. Soc. 1991, 113, 7437.
41. a) S. Okada, S. Peng, W. Spevak, D. Charych, Acc. Chem. Res. 1998, 31, 229;
42. b) U. Jonas, K. Shah, S. Norvez, D. H. Charych, J. Am. Chem. Soc. 1999, 121, 4580;
43. c) J.-M. Kim, Y. B. Lee, D. H. Yang, J.-S. Lee, G. S. Lee, D. J. Ahn, J. Am. Chem. Soc. 2005, 127, 17 580.
44. a) S. Bhattacharya, S. N. G. Acharya, Chem. Mater. 1999, 11, 3121;
45. b) M. Masuda, T. Hanada, Y. Okada, K. Yase, T. Shimizu, Macromolecules 2000, 33, 9233;
46. c) M. George, R. G. Weiss, Chem. Mater. 2003, 15, 2879;
47. d) Z. Yuan, C.-W. Lee, S.-H. Lee, Angew. Chem. 2004, 116, 4293;
48. Angew. Chem. Int. Ed. 2004, 43, 4197;
49. e) T. Mori, K. Shimoyama, Y. Fukawa, K. Minagawa, M. Tanaka, Chem. Lett. 2005, 34, 116.
50. See the Supporting Information.
51. In addition to the fibrils, one could observe an ultrathin layer of 2 which was adsorbed onto the HOPG surface.
52. The apparent height of the fibrils was measured at the maxima of the helical fine structure. The width was estimated from the apparent width of 18 nm after correction for the radius of the SFM tip.
53. Figure 4c shows the SFM picture recorded after UV irradiation. This irradiation, however, had no influence on the appearance of the fibrils in the SFM images.
54. a) F. R. Salemme, Prog. Biophys. Mol. Biol. 1983, 42, 95;
55. b) A. Aggeli, I. A. Nyrkova, M. Bell, R. Harding, L. Carrick, T. C. B. McLeish, A. N. Semenov, N. Boden, Proc. Natl. Acad. Sci. USA 2001, 98, 11 857.