Supramolecular stereomutation in kinetic and thermodynamic self-assembly of helical merocyanine dye nanorods

Angewandte Chemie - International Edition

Volumn 44, Issue 32, 2005, Pages 5071-5074

  Lohr, Andreas ^a   Lysetska, Marina ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Atomic force microscopy; Circular dichroism; Dyes pigments; Merocyanine; Self assembly

Indexed keywords

ATOMIC FORCE MICROSCOPY; AZO DYES; SELF ASSEMBLY; SPECTROSCOPIC ANALYSIS; SUPRAMOLECULAR CHEMISTRY; THERMODYNAMICS;

CIRCULAR DICHROISM (CD); DYES/PIGMENTS; MEROCYANINE; SUPRAMOLECULAR STEREOMUTATION;

NANOSTRUCTURED MATERIALS;

MEROCYANINE DYE; NANOMATERIAL; PYRIMIDINONE DERIVATIVE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; KINETICS; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY;

CIRCULAR DICHROISM; KINETICS; MICROSCOPY, ATOMIC FORCE; MOLECULAR STRUCTURE; NANOSTRUCTURES; PYRIMIDINONES; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; THERMODYNAMICS;

EID: 23944472112     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500640     Document Type: Article

References (44)

1. C. M. Dobson, A. Šali, M. Karplus, Angew. Chem. 1998, 110, 908-935;
2. Angew. Chem. Int. Ed. 1998, 37, 868-893.
3. J. M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, VCH, Weinheim, 1995.
4. For polymeric assemblies see, for example: a) P. Jonkheijm, A. Miura, M. Zdanowska, F. J. M. Hoeben, S. De Feyter, A. P. H. J. Schenning, F. C. De Schryver, E. W. Meijer, Angew. Chem. 2004, 116, 76-80;
5. Angew. Chem. Int. Ed. 2004, 43, 74-78;
6. b) M. Simonyi, Z. Bikádi, F. Zsila, J. Deli, Chirality 2003, 15, 680-698.
7. For metallosupramolecular architectures see, for example: a) A. Hori, K. Yamashita, M. Fujita, Angew. Chem. 2004, 116, 5126-5129;
8. Angew. Chem. Int. Ed. 2004, 43, 5016-5019;
9. b) B. J. Holliday, Y.-M. Jeon, C. A. Mirkin, C. L. Stern, C. D. Incarvito, L. N. Zakharov, R. D. Sommer, A. L. Rheingold, Organometallics 2002, 21, 5713-5725;
10. c) B. Hasenknopf, J. M. Lehn, N. Boumediene, E. Leize, A. Van Dorsselaer, Angew. Chem. 1998, 110, 3458-3460;
11. Angew. Chem. Int. Ed. 1998, 37, 3265-3268.
12. For hydrogen-bonded supramolecular architectures see, for example: a) J. D. Badjić, S. J. Cantrill, J. F. Stoddart, J. Am. Chem. Soc. 2004, 126, 2288-2289;
13. b) V. Paraschiv, M. Crego-Calama, T. Ishi-i, C. J. Padberg, P. Timmerman, D. N. Reinhoudt, J. Am. Chem. Soc. 2002, 124, 7638-7639.
14. For general reviews on helical structures see: a) E. Yashima, K. Maeda, T. Nishimura, Chem. Eur. J. 2004, 10, 43-51;
15. b) C. Schmuck, Angew. Chem. 2003, 115, 2552-2556;
16. Angew. Chem. Int. Ed. 2003, 42, 2448-2452;
17. c) L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097;
18. d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011;
19. e) A. E. Rowan, R. J. M. Nolte, Angew. Chem. 1998, 110, 65-71;
20. Angew. Chem. Int. Ed. 1998, 37, 63-68.
21. a) J. J. D. de Jong, L. N. Lucas, R. M. Kellogg, J. H. van Esch, B. L. Feringa, Science 2004, 304, 278-281;
22. b) S. J. George, A. Ajayaghosh, P. Jonkheijm, A. P. H. J. Schenning, E. W. Meijer, Angew. Chem. 2004, 116, 3504-3507;
23. Angew. Chem. Int. Ed. 2004, 43, 3422-3425;
24. c) C. Keith, R. A. Reddy, U. Baumeister, C. Tschierske, J. Am. Chem. Soc. 2004, 126, 14 312-14 313;
25. d) T. S. Balaban, A. D. Bhise, M. Fischer, M. Linke-Schaetzel, C. Roussel, N. Vanthuyne, Angew. Chem. 2003, 115, 2190-2194;
26. Angew. Chem. Int. Ed. 2003, 42, 2140-2144;
27. e) J. M. Ribo, J. Crusats, F. Sagues, J. Claret, R. Rubires, Science 2001, 292, 2063-2066;
28. f) L. J. Prins, F. De Jong, P. Timmerman, D. N. Reinhoudt, Nature 2000, 408, 181-184;
29. g) R. Oda, I. Huc, M. Schmutz, S. J. Candau, F. C. MacKintosh, Nature 1999, 399, 566-569;
30. h) A. Pawlik, S. Kirstein, U. De Rossi, S. Daehne, J. Phys. Chem. B 1997, 101, 5646-5651.
31. a) F. Würthner, S. Yao, T. Debaerdemaeker, R. Wortmann, J. Am. Chem. Soc. 2002, 124, 9431-9447;
32. b) F. Würthner, S. Yao, B. Heise, C. Tschierske, Chem. Commun. 2001, 2260-2261;
33. c) F. Würthner, S. Yao, J. Org. Chem. 2003, 68, 8943-8949.
34. a) F. Würthner, S. Yao, U. Beginn, Angew. Chem. 2003, 115, 3247-3250;
35. Angew. Chem. Int. Ed. 2003, 42, 3247-3250;
36. b) S. Yao, U. Beginn, T. Gress, M. Lysetska, F. Würthner, J. Am. Chem. Soc. 2004, 126, 8336-8348.
37. F. Würthner, R. Wortmann, K. Meerholz, ChemPhysChem 2002, 3, 17-31.
38. The D-aggregated state is inherently a polymeric strand or cyclic oligomer due to the existence of two receptor sites at each molecule (see ref. [9]).
39. a) N. Berova, K. Nakanishi in Circular Dichroism. Principles and Applications, 2nd ed. (Eds.: N. Berova, K. Nakanishi, R. W. Woody), Wiley, New York, 2000, pp. 337-382;
40. b) V. Buß, C. Reichardt, J. Chem. Soc. Chem. Commun. 1992, 1636-1638.
41. a) V. I. Prokhorenko, D. B. Steensgaard, A. R. Holzwarth, Biophys. J. 2003, 85, 3173-3186;
42. b) C. Didraga, J. A. Klugkist, J. Knoester, J. Phys. Chem. B 2002, 106, 11 474-11 486.
43. a) G. J. Simpson, ChemPhysChem 2004, 5, 1301-1310;
44. b) T. Verbiest, S. Van Elshocht, M. Kauranen, L. Hellemans, J. Snauwaert, C. Nuckolls, T. J. Katz, A. Persoons, Science 1998, 282, 913-915.