Evolution of homochiral helical dye assemblies: Involvement of autocatalysis in the "Majority-rules" effect

Angewandte Chemie - International Edition

Volumn 47, Issue 7, 2008, Pages 1232-1236

  Lohr, Andreas ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Chirality; Circular dichroism; Nanostructures; Self assembly; Supramolecular chemistry

Indexed keywords

AGGLOMERATION; AMPLIFICATION; NANORODS; NANOSTRUCTURES; POLYMERS;

CHIRAL AMPLIFICATION; CHIRALITY; CIRCULAR DICHROISM; HOMOCHIRAL; KINETIC STUDIES; MEROCYANINE; OLIGOMER; SELF-ASSEMBLED; SUPRAMOLECULAR CHEMISTRY;

SELF ASSEMBLY;

COLORING AGENT;

ARTICLE; CATALYSIS; CHEMISTRY; CIRCULAR DICHROISM; KINETICS; STEREOISOMERISM; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY;

CATALYSIS; CIRCULAR DICHROISM; COLORING AGENTS; KINETICS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; THERMODYNAMICS;

EID: 41249087477     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704550     Document Type: Article

References (47)

1. a) J. L. Bada, Nature 1995, 374, 594-595;
2. b) Chirality in Natural and Applied Science (Eds.: W. J. Lough, I. W. Wainer), Blackwell Scientific, Oxford, 2002.
3. a) B. L. Feringa, R. A. van Delden, Angew. Chem. 1999, 111, 3624-3645;
4. Angew. Chem. Int. Ed. 1999, 38, 3418-3438;
5. b) S. C. Nanita, R. G. Cooks, Angew. Chem. 2006, 118, 568-583;
6. Angew. Chem. Int. Ed. 2006, 45, 554-569.
7. a) K. Soai, T. Shibata, H. Morioka, K. Choji, Nature 1995, 378, 767-768;
8. b) M. Klussmann, H. Iwamura, S. P. Mathew, D. H. Wells Jr, U. Pandya, A. Armstrong, D. G. Blackmond, Nature 2006, 441, 621-623.
9. a) M. M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3328-3345;
10. Angew. Chem. Int. Ed. 1999, 38, 3138-3154;
11. b) S. K. Jha, K.-S. Cheon, M. M. Green, J. V. Selinger, J. Am. Chem. Soc. 1999, 121, 1665-1673;
12. c) B. M.W . Langeveld-Voss, R. J. M. Waterval, R. A. J. Jannsen, E. W. Meijer, Macromolecules 1999, 32, 227-230;
13. d) J. J. L. M. Cornelissen, M. Fischer, N. A. J. M. Sommerdijk, R. J. M. Nolte, Science 1998, 280, 1427-1430;
14. e) M. M. Green, B. A. Garetz, B. Munoz, H. Chang, J. Am. Chem. Soc. 1995, 117, 4181-4182.
15. For foldamers with chiral induction see, for example: a) C. Dolain, H. Jiang, J.-M. Léger, P. Guionneau, I. Huc, J. Am. Chem. Soc. 2005, 127, 12943-12951;
16. b) R. B. Prince, L. Brunsveld, E. W. Meijer, J. S. Moore, Angew. Chem. 2000, 112, 234-236;
17. Angew. Chem. Int. Ed. 2000, 39, 228-230.
18. a) E. Yashima, K. Maeda, Y. Okamoto, Nature 1999, 399, 449-451;
19. b) V. Percec. A. E. Dulcey, V. S. K. Balagurusamy, Y. Miura, J. Smidrkal, M. Peterca, S. Nummelin, U. Edlund, S. D. Hudson, P. A. Heiney, H. Duan, S. N. Magonov, S. A. Vinogradov, Nature 2004, 430, 764-768.
20. For "sergeants-and-soldiers" effect in supramolecular systems, see: a) A. R. A. Palmans, J. A. J. M. Vekemans, E. E. Havinga, E. W. Meijer, Angew. Chem. 1997, 109, 2763-2765;
21. Angew. Chem. Int. Ed. Engl. 1997, 36, 2648-2651;
22. b) L. J. Prins, J. Huskens, F. de Jong, P. Timmerman, D. N. Reinhoudt, Nature 1999, 398, 498-502;
23. c) L. J. Prins, P. Timmerman, D. N. Reinhoudt, J. Am. Chem. Soc. 2001, 123, 10153-10163;
24. d) T. Ishi-i, R. Kuwahara, A. Takata, Y. Jeong, K. Sakurai, S. Mataka, Chem. Eur. J. 2006, 12, 763-776;
25. e) A. J. Wilson, J. van Gestel, R. P. Sijbesma, E. W. Meijer, Chem. Commun. 2006, 4404-4406;
26. f) A. Ajayaghosh, R. Varghese, S. J. George, C. Vijayakumar, Angew. Chem. 2006, 118, 1159-1162;
27. Angew. Chem. Int. Ed. 2006, 45, 1141-1144.
28. For "majority-rules" effect in supramolecular systems, see: a) J. Van Gestel, A. R. A. Palmans, B. Titulaer, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2005, 127, 5490-5494;
29. b) W. Jin, T. Fukushima, M. Niki, A. Kosaka, N. Ishii, T. Aida, Proc. Natl. Acad. Sci. USA 2005, 102, 10801-10806;
30. c) A. J. Wilson, M. Masuda, R. P. Sijbesma, E. W. Meijer, Angew. Chem. 2005, 117, 2315-2319;
31. Angew. Chem. Int. Ed. 2005, 44, 2275-2279;
32. d) J. Van Gestel, Macromolecules 2004, 37, 3894-3898.
33. a) F. Würthner, S. Yao, U. Beginn, Angew. Chem. 2003, 115, 3368-3371;
34. Angew. Chem. Int. Ed. 2003, 42, 3247-3250;
35. b) S. Yao, U. Beginn, T. Gress, M. Lysetska, F. Würthner, J. Am. Chem. Soc. 2004, 126, 8336-8348;
36. c) A. Lohr, T. Gress, M. Deppisch, M. Knoll, F. Würthner, Synthesis 2007, 3073-3082.
37. A. Lohr, M. Lysetska, F. Würthner, Angew. Chem. 2005, 117, 5199-5202;
38. Angew. Chem. Int. Ed. 2005, 44, 5071-5074.
39. For experimental details, see the Supporting Information.
40. Analysis of the CD data at the other maxima/minima revealed the same nonlinear behavior.
41. A disappearance of a chiral amplification directed by the "sergeants-and-soldiers" principle over time has been reported: J. J. van Gorp, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2002, 124, 759-14769.
42. a) P. Jonkheijm, P. van der Schoot, A. P. H. J. Schenning, E. W. Meijer, Science 2006, 313, 80-83;
43. b) V. Percec, G. Ungar, M. Peterca, Science 2006, 313, 55-56.
44. The kinetics of the subsequent supramolecular stereomutation of H1 into thermodynamically equilibrated H2 aggregates was not studied in detail here, but was found to proceed very slowly over several days.
45. a) T. S. Balaban, J. Leitich, A. R. Holzwarth, K. Schaffner, J. Phys. Chem. B 2000, 104, 1362-1372;
46. b) T. D. Slavnova, A. K. Chibisov, H. Görner, J. Phys. Chem. A 2005, 109, 4758-4765.
47. D. K. Kondepudi, R. J. Kaufman, N. Singh, Science 1990, 250, 975-976.