Chiral amplification in macromolecular helicity assisted by noncovalent interaction with achiral amines and memory of the helical chirality

Chemistry - A European Journal

Volumn 10, Issue 19, 2004, Pages 4703-4707

  Morino, Kazuhide ^a   Watase, Nobuyuki ^a   Maeda, Katsuhiro ^a   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Chiral amplification; Circular dichroism; Helical structures; Polymers

Indexed keywords

ACETYLENE; ADDITION REACTIONS; ALCOHOLS; AMINES; AMPLIFICATION; COMPLEXATION; POLYMERS; ULTRAVIOLET RADIATION;

ACHIRAL N-BUTYLAMINE; CHIRAL AMPLIFICATION; CO-ADDITION REACTIONS; MACROMOLECULAR HELICITY;

MACROMOLECULES;

ACETYLENE DERIVATIVE; AMINE; BENZENE DERIVATIVE; BUTYLAMINE; NAPHTHYL GROUP; POLYMER;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CONFORMATION; MACROMOLECULE; STEREOSPECIFICITY; ULTRAVIOLET RADIATION;

ACETYLENE; AMINES; CIRCULAR DICHROISM; MOLECULAR CONFORMATION; POLYACETYLENES; POLYMERS;

EID: 5444228791     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400381     Document Type: Article

References (58)

1. For a recent review, see. a) M. M. Green, J.-W Park, T. Sato, A. Teramoto, S Lifson, R. L B Selinger, J V Selinger, Angew Chem 1999, 111, 3329-3345, Angew. Chem Int Ed 1999, 38, 3138-3154,
2. For a recent review, see. a) M. M. Green, J.-W Park, T. Sato, A. Teramoto, S Lifson, R. L B Selinger, J V Selinger, Angew Chem 1999, 111, 3329-3345, Angew. Chem Int Ed 1999, 38, 3138-3154,
3. b) B. L. Feringa, R A van Delden, Angew Chem 1999, 111, 3624-3645, Angew Chem Int Ed 1999, 38, 3418-3438, and references therein.
4. b) B. L. Feringa, R A van Delden, Angew Chem 1999, 111, 3624-3645, Angew Chem Int Ed 1999, 38, 3418-3438, and references therein.
5. Reviews a) R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994,
6. b) C. Girard, H B. Kagan, Angew Chem 1998, 110, 3088-3127; Angew Chem Int Ed 1998, 37, 2922-2959,
7. b) C. Girard, H B. Kagan, Angew Chem 1998, 110, 3088-3127; Angew Chem Int Ed 1998, 37, 2922-2959,
8. c) Catalytic Asymmetric Synthesis, 2nd ed (Eds: I Ojima), Wiley-VCH, Weinheim, 2000;
9. d) R Noyori, Angew Chem 2002, 114, 2108-2123, Angew Chem Int Ed 2002, 47, 2008-2022
10. d) R Noyori, Angew Chem 2002, 114, 2108-2123, Angew Chem Int Ed 2002, 47, 2008-2022
11. a) M M Green, M. P. Reidy, R J Johnson, G Darling, D J O'Leary, G Willson, J. Am Chem Soc 1989, 111, 6452-6454,
12. b) M M. Green, N C Peterson, T Sato, A. Teramoto, R Cook, S. Lifson, Science 1995, 268, 1860-1866;
13. c) S K Jha, K.-S. Cheon, M. M Green, J. V. Selinger, J. Am Chem Soc 1999, 121, 1665-1673.
14. a) E. Yashima, S Huang, T Matsushima, Y Okamoto, Macromolecules 1995, 28, 4184-4193;
15. b) F Takei, K. Onitsuka, S. Takahashi, Polym J 2000, 32, 524-526;
16. c) R Nomura, Y Fukushima, H Nakako, T. Masuda, J. Am Chem Soc 2000, 122, 8830-8836,
17. d) S Toyoda, M Fujiki, Macromolecules 2001, 34, 640-644,
18. e) M Fujiki, Macromol. Rapid Commun. 2001, 22, 539-563,
19. f) K Morino, K. Maeda, Y. Okamoto, E. Yashima, T. Sato, Chem Eur J 2002, 8, 5112-5120.
20. For intermolecular sergeants and soldiers effects in supramolecular system, see a) A. R. A Palmans, J. A J. M Vekemans, E E Havinga, E. W Meijer, Angew. Chem 1997, 109, 2763-2765; Angew Chem Int. Ed Engl 1997, 36, 2648-2651,
21. For intermolecular sergeants and soldiers effects in supramolecular system, see a) A. R. A Palmans, J. A J. M Vekemans, E E Havinga, E. W Meijer, Angew. Chem 1997, 109, 2763-2765; Angew Chem Int. Ed Engl 1997, 36, 2648-2651,
22. b) B M. W Langeved-Voss, R J M Waterval, R. A J. Janssen, E W Meijer, Macromolecules 1999, 32, 227-230,
23. c) L Brunsveld, E W Meijer, R B Prince, J S Moore, J Am Chem Soc 2001, 123, 7978-7984,
24. d) L J. Prins, P. Timmerman, D N Reinhoudt, J Am. Chem Soc 2001, 123, 10153-10163;
25. e) L J. Prins, D N. Reinhoudt, P. Timmerman, Angew Chem 2001, 113, 2446-2492, Angew Chem. Int Ed 2001, 40, 2382-2426,
26. e) L J. Prins, D N. Reinhoudt, P. Timmerman, Angew Chem 2001, 113, 2446-2492, Angew Chem. Int Ed 2001, 40, 2382-2426,
27. f) A P H J Schenning, A F. M. Kilbinger, F Biscarini, M Cavallini, H J Cooper, P. J Derrick, W. J. Feast, R Lazzaroni, P Leclère, L. A. McDonell, E W. Meijer, S. C. J. Meskers, J. Am Chem Soc 2002, 124, 1269-1275,
28. g) I. Huc, Eur. J. Org. Chem 2004, 17-29,
29. for intramolecular sergeants and soldiers effects in supramolecular system, see h) R Fiesel, U. Scherf, Acta Polym 1998, 49, 445-449,
30. i) R B. Prince, J S Moore, L. Brunsveld, E. W Meijer, Chem Eur J 2001, 7, 4150-4154.
31. a) E Yashima, T. Matsushima, Y Okamoto, J Am Chem Soc 1995, 117, 11596-11597,
32. b) E. Yashima, T. Matsushima, Y Okamoto, J Am. Chem Soc 1997, 119, 6345-6359;
33. c) K Maeda, K. Morino, Y Okamoto, T Sato, E Yashima, J Am. Chem Soc 2004, 126, 4329-4342.
34. a) E Yashima, K. Maeda, Y Okamoto, Nature 1999, 599, 449-451,
35. for chirality memory molecules in supramolecular system, see: b) Y. Furusho, T. Kimura, Y Mizuno, T Aida, J Am Chem Soc 1997, 119, 5267-5268;
36. c) T Mizuno, M. Takeuchi, I Hamachi, K, Nakashima, S Shinkai, J. Chem Soc. Perkin Trans 2 1998, 2281-2288;
37. d) A. Sugasaki, M Ikeda, M. Takeuchi, A Robertson, S. Shinkai, J. Chem Soc Perkin Trans 1 1999, 3259-3264,
38. e) J. M Rivera, S. L Craig, T. Martin, J. Rebek, Jr , Angew Chem 2000, 112, 2214-2216, Angew Chem Int Ed 2000, 39, 2130-2132;
39. e) J. M Rivera, S. L Craig, T. Martin, J. Rebek, Jr , Angew Chem 2000, 112, 2214-2216, Angew Chem Int Ed 2000, 39, 2130-2132;
40. f) L J Prins, F. de Jong, P Timmerman, D N Reinhoudt, Nature 2000, 408, 181-184,
41. g) Y Mizuno, T Aida, K. Yamaguchi, J. Am Chem Soc. 2000, 122, 5278-5285,
42. h) Y. Kubo, T. Ohno, J. Yamanaka, T. Tokita, T. Iida, Y. Ishimaru, J Am Chem Soc 2001, 123, 12700-12701;
43. i) R Lauceri, A Raudino, L. M. Scolaro, N. Micali, R Purrello, J Am Chem Soc 2002, 124, 894-895;
44. j) L J Prins, J. J. Verhage, F. de Jong, P Timmerman, D N. Reinhoudt, Chem Eur J 2002, 8, 2302-2313,
45. k) T Ishi-I, M. Crego-Calama, P Timmerman, D. N Reinhoudt, S Shinkai, J Am Chem Soc 2002, 124, 14631-14641,
46. l) M Zieglar, A V Davis, D. W. Johnson, K. N Raymond, Angew Chem 2003, 115, 689-692, Angew. Chem Int Ed 2003, 42, 665-668
47. l) M Zieglar, A V Davis, D. W. Johnson, K. N Raymond, Angew Chem 2003, 115, 689-692, Angew. Chem Int Ed 2003, 42, 665-668
48. -1, respectively These are much larger than that of (R)-2 (57 ± 2); see references [6b, 6c, 7a].
49. 4 and further increased slowly with time These results indicate that the induced helix of the poly-1 is dynamic in nature, the helix-sense and its proportion are determined by the chirality of 2, and (R)-2 complexed with poly-1 can exchange slowly with 5, probably with maintaining the induced macromolecular helicity
50. Water may affect an acid-base complexation in DMSO, and the effect of water on the ICD of poly-1 in the presence of (R)-2 and 5 ([(R)-2]/[poly-1]/[5] = 0 5.1.2.5) was investigated The ICD intensity gradually decreased with an increase in the amount of water, but the effect is negligible when the water content was less than 5%.
51. The ICD intensities of the copolymers of an optically active phenyl-acetylene derivative bearing an (R)-(1-phenylethyl)carbamoyloxy group at the para position and achiral comonomers prepared with a rhodium catalyst increased with an increase in the bulkiness of the substituents on the comonomers.[4a,f] Moreover, the magnitude of the ICD induced on poly-1 with chiral amines had a similar tendency and increased with an increase in the bulkiness of the chiral amines [6]
52. -1, [5]/[poly-1 = 10) by the SEC fractionation by using pure DMSO as the eluent These results indicate that both (R)-2 and 5 complexed with poly-1 are completely removed during the SEC fractionation
53. Recently, chiral amplification has been combined with the chiral memory concept for the successful formation of enantiomeric assemblies, see reference [7k]
54. M A Saito, K. Maeda, H, Onouchi, E. Yashima, Macromolecules 2000, 33, 4616-4618
55. a) C Simionescu, V Percec, S. Dumitrescu, J Polym Sci Polym Chem Ed 1977, 15, 2497-2509,
56. b) C Simionescu, V. Percec, Prog Polym Sci, 1982, 8, 133-214;
57. c) A Furlani, C. V Napoletano, M. V. Russo, W J Feast, Polym. Bull. 1986, 16, 311-317;
58. d) Y Kishimoto, P Eckerle, T Miyatake, M Kainosho, A. Ono, T Ikariya, R Noyori, J Am Chem. Soc 1999, 121, 12035-12044