Chiral arylnickel complexes as highly active initiators for screw-sense selective living polymerization of 1, 2-diisocyanobenzenes

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 48, Issue 4, 2010, Pages 898-904

  Yamada, Tetsuya ^a   Noguchi, Hiroyoshi ^a   Nagata, Yuuya ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chiral initiator; Helical structure; Living polymerization; Polyaromatics

Indexed keywords

ASYMMETRIC POLYMERIZATION; ASYMMETRIC SYNTHESIS; CHIRAL INITIATOR; ENANTIOPURE; HELICAL STRUCTURES; IN-SITU; OPTICALLY ACTIVE; POLYAROMATICS; POLYMERIZATION RATES; QUINOXALINES;

CHLORINE COMPOUNDS; COMPLEXATION; ELECTRON TRANSITIONS; NICKEL ALLOYS; SYNTHESIS (CHEMICAL);

LIVING POLYMERIZATION;

EID: 77955173111     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.23842     Document Type: Article

References (55)

1. (a) Okamoto, Y.; Nakano, T. Chem Rev 1994, 94, 349-372;
2. (b) Nakano, T.; Okamoto, Y. Chem Rev 2001, 101, 4013-4038;
3. (c) Cornelissen, J. J. L.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chem Rev 2001, 101, 4039-4070;
4. (d) Nolte, R. J. M. Chem Soc Rev 1994, 23, 11-19;
5. (e) Rowan, A. E.; Nolte, R. J. M. Angew Chem Int Ed 1998, 37, 63-68;
6. (f) 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;
7. (g) Yashima, E.; Maeda, K.; Nishimura, T. Chem Eur J 2004, 10, 42-51.
8. Okamoto, Y. J Polym Sci Part A: Polym Chem 2009, 47, 1731-1739.
9. Teraguchi, M.; Suzuki, J.; Kaneko, T.; Aoki, T.; Masuda, T. Macromolecules 2003, 36, 9694-9697.
10. (a) Yamamoto, T.; Suginome, M. Angew Chem Int Ed 2009, 48, 539-542;
11. (b) Reggelin, M.; Schults, M.; Holbach, M. Angew Chem Int Ed 2002, 41, 1614-1617;
12. (c) Reggelin, M.; Doerr, S.; Klussmann, M.; Schults, M.; Holbach, M. Proc Natl Acad Sci USA 2004, 101, 5461-5466.
13. (a) Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. J Am Chem Soc 1979, 101, 4763-4765;
14. (b) Nakano, T.; Okamoto, Y.; Hatada, K. J Am Chem Soc 1992, 114, 1318-1329;
15. (c) Hoshikawa, N.; Hotta, Y.; Okamoto, Y. J Am Chem Soc 2003, 125, 12380-12381, and references therein.
16. (a) Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J Am Chem Soc 1988, 110, 6818-6825;
17. (b) Deming, T. J.; Novak, B. M. J Am Chem Soc 1992, 114, 7926-7927. For the discussion on the induction of main chain conformation of polyisocyanides by chiral side chains, see
18. (c) Green, M. M.; Gross, R. A.; Schilling, F. C.; Zero, K.; Crosby, C., III. Macromolecules 1988, 21, 1839-1846.
19. Kaneko, T.; Umeda, Y.; Yamamoto, T.; Teraguchi, M.; Aoki, T. Macromolecules 2005, 40, 9420-9426, and references therein.
20. (a) Gong, G.; Lu, Y.; Novak, B. M. J Am Chem Soc 2004, 126, 4082-4083.
21. (b) Tang, H.-Z.; Garland, E. R.; Novak, B. M.; He, J.; Polavarapu, P. L.; Sun, F. C.; Sheiko, S. S. Macromolecules 2007, 40, 3575-3580.
22. For reviews on the polymerization of isocyanide, see (a) Millich, F. Chem Rev 1972, 72, 101-113;
23. (b) Millich, F. J Polym Sci Macromol Rev 1980, 15, 207-253;
24. (c) Suginome, M.; Ito, Y. Adv Polym Sci 2004, 171, 77-136.
25. (a) Yamamoto, Y.; Takizawa, T.; Hagihara, N. Nippon Kagaku Zasshi 1966, 87, 1355-1359;
26. (b) Saegusa, T.; Ito, Y.; Kobayashi, S.; Hirota, K. Tetrahedron Lett 1967, 8, 521-524;
27. (c) Nolte, R. J. M.; Stephany, R. W.; Drenth, W. Recl Trav Chim Pays-Bas 1973, 83-91;
28. (d) Deming, T. J.; Novak, B. M. Macromolecules 1991, 24, 326-328;
29. (e) Onitsuka, K.; Yanai, K.; Takei, F.; Joh, T.; Takahashi, S. Organometallics 1994, 13, 3862-3867;
30. (f) Deming, T. J.; Novak, B. M.; Ziller, J. W. J Am Chem Soc 1994, 116, 2366-2374;
31. (g) Takei, F.; Tung, S.; Yanai, K.; Onitsuka, K.; Takahashi, S. J. Organomet Chem 1998, 559, 91-96;
32. (h) Cornelissen, J. J. L. M.; Fischer, M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Science 1998, 280, 1427-1430;
33. (i) Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. Eur J 2000, 6, 983-993;
34. (j) Takei, F.; Hayashi, H., Onitsuka, K.; Kobayashi, N.; Takahashi, S. Angew Chem Int Ed 2001, 40, 4092-4094;
35. (k) Cornelissen, J. J. L. M.; Sommerdijk, N. A. J. M.; Nolte, R. J. M. Macromol Chem Phys 2002, 203, 1625-1630;
36. (l) Yamada, Y.; Kawai, T.; Abe, J.; lyoda, T; J Polym Sci Part A: Polym Chem 2002, 40, 399-408;
37. (m) Ishikawa, M.; Maeda, K.; Yashima, E. J Am Chem Soc 2002, 124, 7448-7458;
38. (n) Onitsuka, K.; Yabe, K.-I.; Ohshiro, N.; Shimizu, A.; Okumura, R.; Takei, F.; Takahashi, S. Macromolecules 2004, 37, 8204-8211;
39. (o) Ishikawa, M.; Maeda, K.; Mitsutsuji, Y.; Yashima, E. J Am Chem Soc 2004, 126, 732-733;
40. (p) Kajitani, T.; Okoshi, K.; Sakurai, S.-I.; Kumaki, J.; Yashima, E. J Am Chem Soc 2006, 128, 708-709;
41. (q) Metselaar, G. A.; Schwartz, E.; Gelder, R.; Feiters, M. C.; Nikitenko, S.; Smolentsev, G.; Yalovega, G. E.; Soldatov, A. V.; Cornelissen, J. J. L. M.; Rowan A. E.; Nolte, R. J. M. Chem Phys Chem 2007, 8, 1850-1856;
42. (r) Onitsuka, K.; Mori, T.; Yamamoto, M.; Takei, F.; Takahashi, S. Macromolecules 2006, 39, 7226-7231;
43. (s) Onouchi, H.; Okoshi, K.; Kajitani, T.; Sakurai, S.-I.; Nagai, K.; Kumaki, J.; Onitsuka, K.; Yashima, E. J Am Chem Soc 2008, 130, 229-236.
44. Ito, Y.; Ihara, E.; Murakami, M.; Shiro, M. J Am Chem Soc 1990, 112, 6446-6447.
45. (a) Ito, Y.; Ihara, E.; Murakami, M. Angew Chem Int Ed Engl 1992, 31, 1509-1510;
46. (b) Ito, Y.; Kojima, Y.; Murakami, M. Tetrahedron Lett 1993, 34, 8279-8282;
47. (c) Ito, Y.; Kojima, Y.; Murakami, M.; Suginome, M. Bull Chem Soc Jpn 1997, 70, 2801-2806.
48. (a) Ito, Y.; Ohara, T.; Shima R.; Suginome, M. J Am Chem Soc 1996, 118, 9188-9189;
49. (b) Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara T.; Suginome, M. J Am Chem Soc 1998, 120, 11880-11893;
50. (c) Ito, Y.; Miyake, T.; Ohara, T.; Suginome, M. Macromolecules 1998, 31, 1697-1699;
51. (d) Ito, Y;. Miyake, T.; Suginome, M. Macromolecules 2000, 33, 4034-4038;
52. (e) Sugi- nome, M.; Collet, S.; Ito, Y. Org Lett 2002, 4, 351-354.
53. Ito, Y.; Ihara, E.; Murakami, M. Polym J 1992, 24, 297-299.
54. The new standard has been set on the basis of the g value (Kuhn dissymmetry ratio) of a series of coplymers prepared from achiral 6 and a chiral diisocyanobenzene bearing homochiral side chains with varied ratios. The maximum g value corresponding to 100% P- or M-helical conformation can be elucidated from the plot of the g values against % chiral units in the polymer chain. The new standard g value is almost 10% higher than the previous standard. Yamada, T.; Nagata, Y.; Suginome, M.; Submitted for publication.
55. abs of 1.56 × 10-3.