Synthesis and properties of glutamic acid-derived optically active phenyleneethynylene-based helical polymers

Macromolecules

Volumn 41, Issue 14, 2008, Pages 5089-5097

  Liu, Ruiyuan ^a   Sanda, Fumio ^a   Masuda, Toshio ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b FUKUI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; ORGANIC COMPOUNDS; POLYCONDENSATION;

CARBOXY GROUPS; GLUTAMIC ACID; HELICAL POLYMERS; L-GLUTAMIC ACIDS; OPTICALLY ACTIVE; PHENYLENE-ETHYNYLENE;

POLYMERS;

EID: 48949103767     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma800674f     Document Type: Article

References (56)

1. (a) Tour, J. M. Chem. Rev. 1996, 96, 537.
2. (b) Moore, J. S. Chem. Rev. 1997, 30, 402.
3. (c) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605.
4. (a) Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793.
5. (b) Gin, M. S.; Yokozawa, T.; Prince, R. B.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 2643.
6. (c) Prince, R. B.; Barnes, S. A.; Moore, J. S. J. Am. Chem. Soc. 2000, 122, 2758.
7. (d) Tanatani, A.; Mio, M. J.; Moore, J. S. J. Am. Chem. Soc. 2001, 123, 1792.
8. (e) Heemstra, J. M.; Moore, J. S. J. Am. Chem. Soc. 2004, 126, 1648.
9. Arnt, L.; Tew, G. N. Macromolecules 2004, 37, 1283.
10. (a) Tan, C.; Pinto, M. R.; Kose, M. E.; Ghiviriga, I.; Schanze, K. S. Adv. Mater. 2004, 16, 1208.
11. (b) Zhao, X. Y.; Schanze, K. S. Langmuir 2006, 22, 4856.
12. (a) Inouye, M.; Waki, M.; Abe, H. J. Am. Chem. Soc. 2004, 126, 2022.
13. (b) Abe, H.; Masuda, N.; Waki, M.; Inouye, M. J. Am. Chem. Soc. 2005, 127, 16189.
14. (c) Waki, M.; Abe, H.; Inouye, M. Chem. - Eur. J. 2006, 12, 7839.
15. (a) Prince, R. B.; Saven, J. G.; Wolynes, P. G.; Moore, J. S. J. Am. Chem. Soc. 1999, 121, 3114.
16. (b) Prince, R. B.; Brunsveld, L.; Meijer, E. W.; Moore, J. S. Angew. Chem., Int. Ed. 2000, 39, 228.
17. (c) Brunsveld, L.; Meijer, E. W.; Prince, R. B.; Moore, J. S. J. Am. Chem. Soc. 2001, 123, 7978.
18. Dautel, O. J.; Wantz, G.; Flot, D.; Lere-Porte, J.; Moreau, J. J. E.; Parneix, J.; Serein-Spiraua, F.; Vignau, L. J. Mater. Chem. 2005, 15, 4446.
19. (a) Sanda, F.; Endo, T. Macromol. Chem. Phys. 1999, 200, 2651.
20. (b) Hill D, J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893.
21. (a) Cheuk, K. K. L.; Lam, J. W. Y.; Chen, J.; Lai, L. M.; Tang, B. Z. Macromolecules 2003, 36, 5947.
22. (b) Li, B. S.; Kang, S. Z.; Cheuk, K. K. L.; Wan, L. J.; Ling, L. S.; Bai, C. L.; Tang, B. Z. Langmuir 2004, 20, 7598.
23. (c) Okoshi, K.; Sakajiri, K.; Kumaki, J.; Yashima, E. Macromolecules 2005, 38, 4061.
24. (d) Okoshi, K.; Sakurai, S.; Ohsawa, S.; Yashima, E. Angew. Chem., Int. Ed. 2006, 45, 8173.
25. Sanda, F.; Teraura, T.; Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 4641.
26. (a) Gao, G.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 3932.
27. (b) Sanda, F.; Araki, H.; Masuda, T. Macromolecules 2004, 37, 8510.
28. (c) Zhao, H.; Sanda, F.; Masuda, T. Macromolecules 2004, 37, 8888.
29. Liu, R.; Sanda, F.; Masuda, T. Polymer 2007, 48, 6510.
30. (a) Sanda, F.; Terada, K.; Masuda, T. Macromolecules 2005, 38, 8149.
31. (b) Cheuk, K. K. L.; Lam, J. W. Y.; Lai, L. M.; Dong, Y. P.; Tang, B. Z. Macromolecules 2003, 36, 9752.
32. (a) Staab, H. A.; Nikolic, S. Eur. J. Org. Chem. 1999, 1459.
33. (b) Hamilton, D. G.; Prodi, L.; Feeder, N.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1999, 1, 1057.
34. (c) Hamilton, D. G.; Montalti, M.; Prodi, L.; Fontani, M.; Zanello, P.; Sanders, J. K. M. Chem. - Eur. J. 2000, 6, 608.
35. (d) Hansen, J. G.; Feeder, N.; Hamilton, D. G.; Gunter, M. J.; Becher, J.; Sanders, J. K. M. Org. Lett. 2000, 2, 449.
36. (e) Hansen, J. G.; Bang, K. S.; Thorup, N.; Becker, J. Eur. J. Org. Chem. 2000, 65, 2135.
37. (f) Chen, C.; Lean, J. T.; Alcak, M.; Mallouk, T. E. J. Org. Chem. 2001, 66, 3021.
38. (g) Colquhoun, H. M.; Williams, D. J.; Zhu, Z. J. Am. Chem. Soc. 2002, 124, 13346.
39. (a) Hamilton, D. G.; Davies, J. E.; Prodi, L.; Sanders, J. K. M. Chem. - Eur. J. 1998, 4, 608.
40. (b) Hamilton, D. G.; Feeder, N.; Prodi, L.; Teat, S. J.; Clegg, W.; Sanders, J. K. M. J. Am. Chem. Soc. 1998, 120, 1096.
41. (a) Wang, X.-Z.; Li, X.-Q.; Shao, X.-B.; Zhao, X.; Deng, P.; Jiang, X.-K.; Li, Z.-T.; Chen, Y.-Q. Chem. - Eur. J. 2003, 9, 2904.
42. (b) Vignon, S. A.; Jarrosson, T.; Iijima, T.; Tseng, H.-R.; Sanders, J. K. M.; Stoddart, J. F. J. Am. Chem. Soc. 2004, 126, 9884.
43. (c) Iijima, T.; Vignon, S. A.; Tseng, H.-R.; Jarrosson, T.; Sanders, J. K. M.; Marchioni, F.; Venturi, M.; Apostoli, E.; Balzani, V.; Stoddart, J. F. Chem. - Eur. J. 2004, 10, 6375.
44. (a) Iwanaga, T.; Yasutake, M.; Takemura, H.; Sako, K.; Shinmyozu, T. Angew. Chem., Int. Ed. 2006, 45, 3643.
45. (b) Kato, S.; Matsumoto, T.; Ideta, K.; Shimasaki, T.; Goto, K.; Shinmyozu, T. J. Org. Chem. 2006, 71, 4723.
46. (c) Chen, Z.; Stepanenko, V.; Dehm, V.; Prins, P.; Siebbeles, L. D. A.; Seibt, J.; Marquetand, P.; Engel, V.; Wurthner, F. Chem. - Eur. J. 2007, 13, 436.
47. (d) Chen, Z.; Baumeister, U.; Tschierske, C.; Wurthner, F. Chem. - Eur. J. 2007, 13, 450.
48. 2 in hexane (2.17 mL, 1.3 mmol) was added to a solution of poly(1-2p)′ or poly(1-2m)′ (722 mg, 1 mmol) in DMF (5.0 mL) and MeOH (2.0 mL) at room temperature. The resulting mixture was stirred at room temperature for 30 min and then concentrated to a volume of 5.0 mL. The resulting solution was poured into a large amount of MeOH to precipitate a polymer. It was separated by filtration using a membrane filter (ADVANTEC H100A047A) and dried under reduced pressure.
49. Kuhn, W. Trans. Faraday Soc. 1930, 26, 293.
50. (a) Fujiki, M. Appl. Phys. Lett. 1994, 65, 3251.
51. (b) Fujiki, M. J. Am. Chem. Soc. 1994, 116, 6017.
52. (c) Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539.
53. (d) Kim, S. Y.; Fujiki, M.; Ohira, A.; Kwak, G.; Kawakami, Y. Macromolecules 2004, 37, 4321.
54. Li, B. S.; Cheuk, K. K. L.; Ling, L.; Chen, J.; Xiao, X.; Bai, C.; Tang, B. Z. Macromolecules 2003, 36, 77.
55. (a) Kukula, H.; Schlaad, H.; Antonietti, M.; Förster, S. J. Am. Chem. Soc. 2002, 124, 1658.
56. (b) Chécot, F.; Brûlet, A.; Oberdisse, J.; Gnanou, Y.; Mondain-Monval, O.; Lecommandoux, S. Langmuir 2005, 21, 4308.