Synthesis of a stimuli-responsive P-chiral polymer with chiral phosphorus atoms and azobenzene moieties in the main chain

Chemistry - An Asian Journal

Volumn 2, Issue 3, 2007, Pages 397-402

  Ouchi, Yuko ^a   Morisaki, Yasuhiro ^a   Ogoshi, Tomoki ^a   Chujo, Yoshiki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Azobenzene; Chiral phosphorus atoms; Isomerization; Polymerization; Stimuli response

Indexed keywords

AZO COMPOUND; AZOBENZENE; PHOSPHINE DERIVATIVE; PLATINUM COMPLEX; POLYMER;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AZO COMPOUNDS; CIRCULAR DICHROISM; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOPLATINUM COMPOUNDS; PHOSPHINES; PHOTOCHEMISTRY; POLYMERS; STEREOISOMERISM;

EID: 34248169151     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600378     Document Type: Article

References (58)

1. L. Pauling, R. B. Corey, H. R. Branson, Proc. Natl. Acad. Sci. USA 1951, 37, 205.
2. J. D. Watson, F. H. C. Crick, Nature 1953, 171, 737.
3. G. E. Schulz, R. H. Schirmer, Principles of Protein Structure, Springer, New York, 1979.
4. W. Saenger, Principles of Nucleic Acid Structure, Springer, New York, 1984.
5. C. Branden, J. Tooze, Introduction of Protein Structure, 2nd ed., Garland Publishing, New York, 1999.
6. Y. Okamoto, T. Nakano, Chem. Rev. 1994, 94, 349.
7. Y. Okamoto, T. Nakano, Chem. Rev. 2001, 101, 4013.
8. G. W. Coates, R. M. Waymouth, J. Am. Chem. Soc. 1991, 113, 6270.
9. J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk, Chem. Rev. 2001, 101, 4039.
10. K. Nozaki, N. Sato, H. Takaya, J. Am. Chem. Soc. 1995, 117, 9911.
11. K. Nozaki, K. Nakano, T. Hiyama, J. Am. Chem. Soc. 1999, 121. 11008.
12. K. Nozaki, N. Kosaka, V. M. Graubner, T. Hiyama, Polym. J. 2002, 34, 376.
13. M. Fujiki, J. Am. Chem. Soc. 2000, 122, 3336.
14. M. Fujiki, Macromol. Rapid Commun. 2001, 22, 539.
15. M. M. Green, J-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3328;
16. Angew. Chem. Int. Ed. 1999, 38, 3138.
17. R. Nomura, Y. Fukushima, H. Nakako, T. Masuda, J. Am. Chem. Soc. 2000, 122, 8830.
18. R. Nomura, J. Tabei, T. Masuda, J. Am. Chem. Soc. 2001, 123, 8430.
19. C. Yamamoto, Y. Okamoto, Bull. Chem. Soc. Jpn. 2004, 77, 227.
20. J. W. Y. Lam, B. Z. Tang, Acc. Chem. Res. 2005, 38, 745.
21. L. Pu, Acta. Polym. 1997, 48, 116.
22. L. Pu, Chem. Rev. 1998, 98, 2405.
23. E. Yashima, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1997, 119, 6345.
24. E. Yashima, K. Maeda, Y. Okamoto, Nature 1999, 399, 449.
25. E. Yashima, K. Maeda, T. Yamanaka, J. Am. Chem. Soc. 2000, 122, 7813.
26. H. Onouchi, T. Miyagawa, A. Furuko, K. Maeda, E. Yashima, J. Am. Chem. Soc. 2005, 127, 2960.
27. C. Piguet, G. Bernardinelli, G. Hopfgartner, Chem. Rev. 1997, 97, 2005.
28. D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893.
29. T. Iwasaki, Y. Kohinata, H. Nishide, Org. Lett. 2005, 7, 755.
30. A. E. Rowan, R. J. M. Nolte, Angew. Chem. 1998, 110, 65;
31. Angew. Chem. Int. Ed. 1998, 37, 63.
32. For Si atom: Y. Kawakami, K. Takeyama, K. Komuro, O. Ooi, Macromolecules 1998, 31, 551.
33. For Si atom: Y. Kawakami, D. Zhou, Macromolecules 2005, 38, 6902.
34. For S atom: T. Oyama, Y. Chujo, Macromolecules 1999, 32, 7732.
35. For S atom: A. Angeloni, M. Laus, D. Caretti, E. Chiellini, G. Galli, Makromol. Chem. 1990, 191, 2787.
36. K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375.
37. R. D. Baechler, K. Mislow, J. Am. Chem. Soc. 1970, 92, 3090.
38. Y. Morisaki, Y. Ouchi, T. Fukui, K. Naka, Y. Chujo, Tetrahedron Lett. 2005, 46, 7011.
39. T. Imamoto, J. Watanabe, Y. Wada, H. Masuda, H. Yamada, H. Tsuruta, S. Matsukawa, K. Yamaguchi, J. Am. Chem. Soc. 1998, 120, 1635.
40. Wild and co-workers reported the synthesis and isolation of three types of optically active hexaphosphines with four P-chiral centers by another approach, and a unique double-stranded parallel helicate of the copper complex was characterized: P. K. Bowyer, V. C. Cook, N. Gharib-Naseri, P. A. Gugger, A. D. Rae, G. F. Swiegers, A. C. Willis, J. Zank, S. B. Wild, Proc. Natl. Acad. Sci. USA 2002, 99, 4877.
41. Y. Morisaki, Y. Ouchi, K. Tsurui, Y. Chujo, J. Polym. Sci. Part A: Polym. Chem. 2007, in press.
42. B. L. Feringa, R. A. van Dalden, N. Koumura, E. M. Geertsema, Chem. Rev. 2000, 100, 1789.
43. O. Pieroni, A. Fissi, N. Angelini, F. Lenci, Acc. Chem. Res. 2001, 34, 9.
44. M. M. Green, M. P. Reidy, J. Am. Chem. Soc. 1989, 111, 6452.
45. N. Hida, F. Takei, K. Onitsuka, K. Shida, S. Asaoka, T. Iyoda, S. Takahashi, Angew. Chem. 2003, 115, 4485;
46. Angew. Chem. Int. Ed. 2003, 42, 4349.
47. M. Müller, R. Zentel, Macromolecules 1994, 27, 4404.
48. L. Angiolini, R. Bozio, L. Giorgini, D. Pedron, G. Turco, A. Daurù, Chem. Eur. J. 2002, 8, 4241.
49. N. Kosaka, T. Oda, T. Hiyama, K. Nozaki, Macromolecules 2004, 37, 3159.
50. L. A. Howe, G. D. Jaycox, J. Polym. Sci. Part A: Polym. Chem. 1998, 36, 2827.
51. G. S. Kumar, D. C. Neckers, Chem. Rev. 1989, 89, 1915.
52. S. Xie, A. Natansohn, P. Rochon, Chem. Mater. 1993, 5, 403.
53. A. Natansohn, P. Rochon, Adv. Mater. 1999, 11, 1387.
54. A. Natansohn, P. Rochon, Chem. Rev. 2002, 102, 4139.
55. A. Izumi, M. Teraguchi, R. Noura, T. Masuda, Macromolecules 2000, 33, 5347.
56. H. Zollinger, Azo and Diazo Chemistry, Interscience, New York, 1961.
57. Q. Guo, Z. Zhong, Mater. Sci. Eng. C 2000, 7, 91.
58. Almost no changes of the molecular weights of the polymer were observed during the isomerization process.