Synthesis of helical rod-coil multiblock copolymers by living block copolymerization of isocyanide and 1,2-diisocyanobenzene using arylnickel initiators

Macromolecules

Volumn 43, Issue 9, 2010, Pages 3999-4002

  Yamada, Tetsuya ^a   Suginome, Michinori ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BLOCK COPOLYMERIZATION; CIRCULAR DICHROISM SPECTRA; GOOD YIELD; HELICAL RODS; HELICAL STRUCTURES; ISOCYANIDES; MULTIBLOCK COPOLYMER; OPTICALLY ACTIVE; PHENYL ISOCYANIDE; QUINOXALINES; RIGHT HANDED;

COPOLYMERIZATION; DICHROISM; PALLADIUM; POLYMERS; SYNTHESIS (CHEMICAL);

CYANIDES;

EID: 77951914061     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma100500r     Document Type: Article

References (49)

1. Kim, H.-C.; Park, S.-M.; Hinsberg, W. D. Chem. Rev. 2010, 110, 146
2. Lee, M.; Cho, B.-K.; Zin, W.-C. Chem. Rev. 2001, 101, 3869
3. Kamigaito, M.; Ando, T.; Sawamoto, M. Chem. Rev. 2001, 101, 3689
4. Aoshima, S.; Kanaoka, S. Chem. Rev. 2009, 109, 5245
5. Hadjichristidis, N.; Pitsikalis, M.; Pispas, S.; Iatrou, H. Chem. Rev. 2001, 101, 3747
6. Chen, E. Y.-X. Chem. Rev. 2009, 109, 5157
7. Yamamoto, Y.; Takizawa, T.; Hagihara, N. Nippon Kagaku Zasshi 1966, 87, 1355
8. Saegusa, T.; Ito, Y.; Kobayashi, S.; Hirota, K. Tetrahedron Lett. 1967, 8, 521
9. Otsuka, S.; Nakamura, A.; Yoshida, T. J. Am. Chem. Soc. 1969, 91, 7196
10. Nolte, R. J. M.; Stephany, R. W.; Drenth, W. Recl. Trav. Chim. Pays-Bas 1973, 92, 83
11. Ogawa, H.; Joh, T.; Takahashi, S. J. Chem. Soc., Chem. Commun. 1988, 561
12. Deming, T. J.; Novak, B. M. Macromolecules 1991, 24, 326
13. Yamamoto, M.; Onitsuka, K.; Takahashi, S. Organometallics 2000, 19, 4669
14. For review, see: Suginome, M.; Ito, Y. Adv. Polym. Sci. 2004, 171, 77
15. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Chem. Soc., Chem. Commun. 1986, 1789
16. Kamer, P. C. J.; Nolte, R. J. M.; Drenth, W. J. Am. Chem. Soc. 1988, 110, 6818
17. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 7926
18. Benjamin, A. J. M.; Nolte, R. J. M.; Zwikker, J. W.; Drenth, B. M. J. Mol. Catal. 1978, 4, 427
19. Benjamin, A. J. M.; Nolte, R. J. M.; Drenth, B. M.; Hezemans, A. M. F.; van de Coolwijk, P. J. F. M. Macromolecules 1980, 13, 1386
20. Benjamin, A. J. M.; Nolte, R. J. M.; Naaktgeboren, A. J.; Zwikker, J. W.; Drenth, B. M.; Hezemans, A. M. F. Macromolecules 1983, 16, 1679
21. Deming, T. J.; Novak, B. M. J. Am. Chem. Soc. 1992, 114, 4400
22. Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Angew. Chem., Int. Ed. 1996, 35, 1554
23. Takei, F.; Yanai, K.; Onitsuka, K.; Takahashi, S. Chem. - Eur. J. 2000, 6, 983
24. Takei, F.; Hayashi, H.; Onitsuka, K.; Kobayaashi, N.; Takahashi, S. Angew. Chem., Int. Ed. 2001, 40, 4092
25. Amabilino, D. B.; Ramos, E.; Serrano, J.-L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1998, 120, 9126
26. Ishikawa, M.; Maeda, K.; Yashima., E. J. Am. Chem. Soc. 2002, 124, 7448
27. Hase, Y.; Ishikawa, M.; Muraki, R.; Maeda, K.; Yashima, E. Macromolecules 2006, 39, 6003
28. Hase, Y.; Nagai, K.; Iida, H.; Maeda, K.; Ochi, N.; Sawabe, K.; Sakajiri, K.; Okoshi, K.; Yashima, E. J. Am. Chem. Soc. 2009, 131, 10719
29. Yamamoto, Y.; Yamazaki, H. Bull. Chem. Soc. Jpn. 1970, 43, 2653
30. Yamamoto, Y.; Yamazaki, H. Inorg. Chem. 1974, 13, 438
31. Hong, B.; Fox, M. A. Macromolecules 1994, 27, 5311
32. Hong, B.; Fox., M. A. Can. J. Chem. 1995, 73, 2101
33. Ito, Y.; Ihara, E.; Murakami, M.; Shiro, M. J. Am. Chem. Soc. 1990, 112, 6446
34. Ito, Y.; Ihara, E.; Murakami, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 1509
35. Ito, Y.; Kojima, Y.; Murakami, M. Tetrahedron Lett. 1993, 34, 8279
36. Ito, Y.; Kojima, Y.; Murakami, M.; Suginome, M. Bull. Chem. Soc. Jpn. 1997, 70, 2801
37. Ito, Y.; Ohara, T.; Shima, R.; Suginome, M. J. Am. Chem. Soc. 1996, 118, 9188
38. Ito, Y.; Miyake, T.; Hatano, S.; Shima, R.; Ohara, T.; Suginome, M. J. Am. Chem. Soc. 1998, 120, 11880
39. Ito, Y.; Miyake, T.; Ohara, T.; Suginome, M. Macromolecules 1998, 31, 1697
40. Ito, Y.; Miyake, T.; Suginome, M. Macromolecules 2000, 33, 4034
41. Suginome, M.; Collet, S.; Ito, Y. Org. Lett. 2002, 4, 351
42. Ito, Y.; Ihara, E.; Murakami, M. Polym. J. 1992, 24, 297
43. Yamada, T.; Noguchi, H.; Nagata, Y.; Suginome, M. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 898
44. Deming, T. J.; Novak, B. M. Macromolecules 1991, 24, 5478
45. Deming, T. J.; Novak, B. M.; Ziller, J. W. J. Am. Chem. Soc. 1994, 116, 2366
46. Tomita, I.; Taguchi, M.; Takagi, K.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 35, 431
47. Kros, A.; Jesse, W.; Metselaar, G. A.; Cornelissen, J. J. L. M. Angew. Chem., Int. Ed. 2005, 44, 4349
48. See the Supporting Information for the UV and CD spectra of poly(iminomethylene)s and poly(quinoxaline)s.
49. The screw-sense excesses of the helical quinoxaline rods of the block copolymers were estimated on the assumption that their UV and CD spectra were the linear combinations of the spectra of polyquinoxaline and poly(iminomethylene) homopolymers. This treatment affords virtual CD and UV spectra of the polyquinoxaline blocks of the block copolymers, leading to virtual g value for the polyquinoxaline block, which corresponds to the screw-sense excess. This treatment, however, is not applicable to the estimation of the se of poly(iminomethylene) block because it is difficult to obtain virtual CD spectra of the poly(iminomethylene) block due to much weaker CD intensity of the poly(iminomethylene) structure than that of poly(quinoxaline) block. See the Supporting Information for details.