Helix-sense-controlled polymerization of optically active phenyl isocyanides

Macromolecules

Volumn 41, Issue 5, 2008, Pages 1601-1611

  Kajitani, Takashi ^a   Okoshi, Kento ^a   Yashima, Eiji ^a,b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; FUNCTIONAL GROUPS; LACTIC ACID; POLYMERIZATION;

OPTICALLY ACTIVE; PHENYL ISOCYANIDES;

CYANIDES;

EID: 41849108829     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma7022952     Document Type: Article

References (70)

1. For examples, see: (a) Yu, S. M.; Conticello, V. P.; Zhang, G.; Kayser, C.; Fourinier, M. J.; Mason, T. L.; Tirrell, D. A. Nature (London) 1997, 389, 167-170.
2. (b) Green, M. M.; Zanella, S.; Gu, H.; Sato, T.; Gottarelli, G.; Jha, S. K.; Spada, G. P.; Schoevaars, A. M.; Feringa, B.; Teramoto, A. J. Am. Chem. Soc. 1998, 120, 9810-9817.
3. (c) Watanabe, J.; Kamee, H.; Fujiki, M. Polym. J. 2001, 33, 495-497.
4. (d) Cornelissen, J. J. L. M.; Donners, J. J. J. M.; de Gelder, R.; Graswinckel, W. S.; Metselaar, G. A.; Rowan, A. E.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Science 2001, 293, 676-680.
5. (e) Cornelissen, J. J. L. M.; Graswinckel, W. S.; Rowan, A. E.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1725-1736.
6. (f) Kim, J.; Novak, B. M. Macromolecules 2004, 37, 1660-1662.
7. (g) Tian, G.; Lu, Y.; Novak, B. M. J. Am. Chem. Soc. 2004, 126, 4082-4083.
8. (h) Maeda, K.; Takeyama, Y.; Sakajiri, K.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 16284-16285.
9. (i) Okoshi, K.; Sakajiri, K.; Kumaki, J.; Yashima, E. Macromolecules 2005, 38, 4061-4064.
10. (j) Metselaar, G. A.; Wezenberg, S. J.; Cornelissen, J. J. L. M.; Nolte, R. J. M.; Rowan, A. E. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 981-988.
11. (a) Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1021-1043.
12. (b) Yashima, E. J. Chromatogr. A 2001, 906, 105-125.
13. (c) Nakano, T. J. Chromatogr. A 2001, 906, 205-225.
14. (d) Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013-4038.
15. (e) Yamamoto, C.; Okamoto, Y. Bull. Chem. Soc. Jpn. 2004, 77, 227-257.
16. For reviews on helical polymers, see ref 2d and: (a) Green, M. M.; Park, J.-W.; Sato, T.; Teramoto, A.; Lifson, S.; Selinger, R. L. B.; Selinger, J. V. Angew. Chem., Int. Ed. 1999, 38, 3138-3154.
17. (b) Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. J. A. M. Chem. Rev. 2001, 101, 4039-4070.
18. (c) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563.
19. (d) Nomura, R.; Nakano, H.; Masuda, T. J. Mol. Catal. A 2002, 190, 197-205.
20. (e) Yashima, E.; Maeda, K.; Nishimura, T. Chem.-Eur. J. 2004, 10, 43-51.
21. (f) Lam, J. W. Y.; Tang, B. Z. Ace. Chem. Res. 2005, 38, 745-754.
22. For reviews on helical polyisocyanides, see ref 3b and: (a) Millich, F. Chem. Rev. 1972, 72, 101-113.
23. (b) Millich, F. Adv. Polym. Sci. 1975, 19, 117-141.
24. (c) Drenth, W.; Nolte, R. J. M. Acc. Chem. Res. 1979, 12, 30-35.
25. (d) Nolte, R. J. M. Chem. Soc. Rev. 1994, 23, 11-19.
26. (e) Takahashi, S.; Onitsuka, K.; Takei, F. Proc. Jpn. Acad. 1998, 74(B), 25-30.
27. (f) Suginome, M.; Ito, Y. Adv. Polym. Sci. 2004, 171, 77-136.
28. (g) Amabilino, D. B.; Serrano, J.-L.; Sierra, T.; Veciana, J. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 3161-3174. For other leading references on helical polyisocyanides, see:
29. (h) Kamer, P. C. J.; Cleij, M. C.; Nolte, R. J. M.; Harada, T.; Hezemans, A. M. F.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 1581-1587.
30. (i) Green, M. M.; Gross, R. A.; Schilling, F. C.; Zero, K.; Crosby, C. I. Macromolecules 1988, 21, 1839-1846.
31. (j) Pini, D.; Iuliano, A.; Salvadori, P. Macromolecules 1992, 25, 6059-6062.
32. (k) Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Angew. Chem., Int. Ed. 1996, 35, 1554-1556.
33. (l) Spencer, L.; Kim, M.; Euler, W. B.; Rosen, W. J. Am. Chem. Soc. 1997, 119, 8129-8130.
34. (m) Cornelissen, J. J. L. M.; Fischer, M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Science 1998, 280, 1427-1430.
35. (n) Amabilino, D. B.; Ramos, E.; Serrano, J.-L.; Veciana, J. Adv. Mater. 1998, 10, 1001-1005.
36. (o) Amabilino, D. B.; Ramos, E.; Serrano, J. -L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1998, 120, 9126-9134.
37. (p) Hasegawa, T.; Kondoh, S.; Matsuura, K.; Kobayashi, K. Macromolecules 1999, 32, 6595-6603.
38. (q) Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem.-Eur. J. 2000, 6, 983-993.
39. (r) Yamada, Y.; Kawai, T.; Abe, J.; Iyoda, T. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 399-408.
40. (s) Metselaar, G. A.; Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M. Angew. Chem., Int. Ed. 2005, 44, 1990-1993.
41. (t) Amabilino, D. B.; Ramos, E.; Serrano, J.-L.; Sierra, T.; Veciana, J. Polymer 2005, 46, 1507-1521.
42. (u) Onitsuka, K.; Mori, T.; Yamamoto, M.; Takei, F.; Takahashi, S. Macromolecules 2006, 39, 7224-7231.
43. (a) van Beijnen, A. J. M.; Nolte, R. J. M.; Drenth, W.; Hezemans, A. M. F. Tetrahedron 1976, 32, 2017-2019.
44. (b) van Beijnen, A. J. M.; Nolte, R. J. M.; Naaktgebornen, A. J.; Zwikker, J. W.; Drenth, W.; Hezemans, A. M. F. Macromolecules 1983, 16, 1679-1689.
45. (c) Takei, F.; Hayashi, H.; Onitsuka, K.; Kobayashi, N.; Takahashi, S. Angew. Chem., Int. Ed. 2001, 40, 4092-4094.
46. (d) Cornelissen, J. J. L. M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Macromol. Chem. Phys. 2002, 203, 1625-1630. Recently, the helical structure of an optically active polyisocyanide was determined to be a 15 units/4 turns (15/4) helix with a helical pitch of 1.28 nm on the basis of X-ray diffraction combined with high-resolution atomic force microscopy (AFM) observations. See:
47. (e) Onouchi, H.; Okoshi, K.; Kajitani, T.; Sakurai, S.-i.; Nagai, K.; Onitsuka, K.; Yashima, E. J. Am. Chem. Soc. 2008, 130, 229-236.
48. Nolte, R. J. M.; van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932-5933.
49. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818-6825.
50. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926-7927.
51. (a) Kauranen, K.; Verbiest, T.; Boutton, C.; Teerenstra, M. N.; Schouten, A. J.; Nolte, R. J. M.; Persoons, A. Science 1995, 270, 966-969.
52. (b) Cornelissen, J. J. L. M.; Graswinckel, W. S.; Adams, P. J. H. M.; Nachtegaal, G. H.; Kentgens, A. P. M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 4255-4264.
53. (c) Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458.
54. (d) Gomar-Nadal, E.; Veciana, J.; Rovira, C.; Amabilino, D. B. Adv. Mater. 2005, 17, 2095-2098.
55. (e) Kros, A.; Jesse, W.; Metselaar, G. A.; Cornelissen, J. J. L. M. Angew. Chem., Int. Ed. 2005, 44, 4349-4352.
56. (f) Tian, Y.; Kamata, K.; Yoshida, H.; Iyoda, T. Chem-Eur. J. 2006, 12, 584-591.
57. (g) Hase, Y.; Mitsutsuji, Y.; Ishikawa, M.; Maeda, K.; Okoshi, K.; Yashima, E. Chem. Asian J. 2007, 2, 755-763.
58. Kajitani, T.; Okoshi, K.; Sakurai, S.-i.; Kumaki, J.; Yashima, E. J. Am. Chem. Soc. 2006, 128, 708-709.
59. 5e,10
60. For the hydrogen-bond-assisted helical polymers except for poly(isocyanopeptides)s, see: (a) Nomura, R.; Tabei, J.; Masuda, T. J. Am. Chem. Soc. 2001, 123, 8430-8431.
61. (b) Li, B. S.; Cheuk, K. K. L.; Ling, L.; Chen, J.; Xiao, X.; Bai, C.; Tang, B. Z. Macromolecules 2003, 36, 77-85.
62. Reichardt, C. In Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003; pp 375-388.
63. A similar increase in the CD intensity upon heating was recently reported for the poly(aryl isocyanide)s with chiral pendants. See: (a) Takei, F.; Onitsuka, K.; Takahashi, S. Macromolecules 2005, 38, 1513-1516. For other reversible and irreversible changes in the CD spectral patterns by temperature or reduction-oxidation cycles, see:
64. (b) Hida, N.; Takei, F.; Onitsuka, K.; Shiga, K.; Asaoka, S.; Iyoda, T.; Takahashi, S. Angew. Chem., Int. Ed. 2003, 42, 4349-4352.
65. (c) Amabilino, D. B.; Serrano, J.-L.; Veciana, J. Chem. Commun. 2005, 322-324.
66. (d) Wezenberg, S. J.; Metselaar, G. A.; Rowan, A. E.; Cornelissen, J. J. L. M.; Seebach, D.; Nolte, R. J. M. Chem.-Eur. J. 2006, 12, 2778-2786.
67. (e) Metselaar, G. A.; Adams, P. J. H. M.; Nolte, R. J. M.; Cornelissen, J. J. L. M.; Rowan, A. E. Chem.-Eur. J. 2007, 13, 950-960.
68. 1st value of ca. 5 % after annealing in a mixture of toluene and dimethylformamide (DMF) (3:2, v/v) at 100°C for 445 h.
69. (a) Yamagishi, A.; Tanaka, I.; Taniguchi, M.; Takahashi, M. J. Chem. Soc., Chem. Commun. 1994, 1113-1114.
70. (b) Tsuchida, A.; Hasegawa, T.; Kobayashi, K.; Yamamoto, C.; Okamoto, Y. Bull. Chem. Soc. Jpn. 2002, 75, 2681-2685.