Chiral stimuli-responsive gels: Helicity induction in poly(phenylacetylene) gels bearing a carboxyl group with chiral amines

Journal of the American Chemical Society

Volumn 125, Issue 9, 2003, Pages 2516-2523

  Goto, Hidetoshi ^a   Zhang, Hao Qian ^a   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDUCED CIRCULAR DICHROISM (ICD);

ALCOHOLS; AMINES; AMINO ACIDS; CATALYSTS; COPOLYMERIZATION; CROSSLINKING; SWELLING; SYNTHESIS (CHEMICAL);

GELS;

ACETYLENE DERIVATIVE; AMINE; AMINO ACID; AMINOALCOHOL; CARBOXYL GROUP; DIAMINE; DIMETHYL SULFOXIDE; POLY(PHENYLACETYLENE); POLYMER; RHODIUM COMPLEX; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYST; CHIRALITY; CIRCULAR DICHROISM; CROSS LINKING; GEL; POLYMERIZATION; SYNTHESIS;

EID: 0037420325     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029036c     Document Type: Article

References (76)

1. (a) Qiu, Y.; Park, K. Adv. Drug Delivery Rev. 2001, 53, 321-339.
2. (b) Jeong, B.; Gutowska, A. Trends Biotechnol. 2002, 20, 305-311.
3. (a) Tanaka, T. Phys. Rev. Lett. 1978, 40, 820-823.
4. (b) Tanaka, T.; Fillmore, D.; Sun, S.-T.; Nishio, I.; Swislow, G.; Shah, A. Phys. Rev. Lett. 1980, 45, 1636-1639.
5. (c) Hirokawa, Y.; Tanaka, T. J. Chem. Phys. 1984, 85, 6379-6380.
6. (d) Chen, G.; Hoffman, A. S. Nature 1995, 373, 49-52.
7. (e) Yoshida, R.; Uchida, K.; Kaneko, Y.; Sakai, K.; Kikuchi, A.; Sakurai, Y.; Okano, T. Nature 1995, 374, 240-242.
8. (f) Grinberg, V. Y.; Grinberg, N. V.; Mikheeva, L. M.; Dembo, A. T.; Makhaeva, E. E.; Khokhlov, A. R.; Grosberg, A. Y.; Tanaka, T. Macromol. Chem. Phys. 1999, 200, 1603-1607.
9. (g) Yamamoto, K.; Serizawa, T.; Muraoka, Y.; Akashi, M. Macromolecules 2001, 34, 8014-8020.
10. (h) Jeong, B.; Kim, S. W.; Bae, Y. H. Adv. Drug Delivery Rev. 2002, 54, 37-51 and references therein.
11. (a) Tokita, T.; Nishio, I.; Sun, S.-T.; Ueno-Nishio, S. Science 1982, 218, 467-469.
12. (b) Zrínyi, M. Colloid Polym. Sci. 2000, 278, 98-103.
13. (a) Irie, M.; Kungwachakun, D. Makromol. Chem., Rapid Commun. 1984, 5, 829-833.
14. (b) Juodkazis, S.; Mukai, N.; Wakaki, R.; Yamaguchi, A.; Matsuo, S.; Misawa, H. Nature 2000, 408, 178-181.
15. (a) Osada, Y.; Okuzaki, H.; Hori, H. Nature 1992, 355, 242-244.
16. (b) Hu, Z.; Zhang, X.; Li, Y. Science 1995, 269, 525-527.
17. (c) Osada, Y.; Gong, J. P. Adv. Mater. 1998, 10, 827-837.
18. (d) Kaneko, D.; Gong, J. P.; Osada, Y. J. Mater. Chem. 2002, 12, 2169-2177.
19. (a) Osada, Y.; Matsuda, A. Nature 1995, 376, 219.
20. (b) Kagami, T.; Gong, J. P.; Osada, Y. Macromol. Rapid Commun. 1996, 17, 539-543.
21. (c) Kim, B. K.; Lee, S. Y.; Lee, J. S.; Baek, S. H.; Choi, Y. J.; Lee, J. O.; Xu, M. Polymer 1998, 13, 2803-2808.
22. (d) Lendlein, A.; Schmidt, A. M.; Langer, R. Proc. Natl. Acad. Sci. U.S.A. 2000, 98, 842-847.
23. (a) Kikuchi, A.; Okano, T. Adv. Drug Delivery Rev. 2002, 54, 53-77.
24. (b) Miyata, T.; Uragami, T.; Nakamae, K. Adv. Drug Delivery Rev. 2002, 54, 79-98.
25. (c) Byrne, M. E.; Park, K.; Peppas, N. A. Adv. Drug Delivery Rev. 2002, 54, 149-161.
26. (a) Holtz, J. H.; Asher, S. A. Nature 1997, 389, 829-832.
27. (b) Holtz, J. H.; Holtz, J. S. W.; Munro, C. H.; Asher, S. A. Anal. Chem. 1998, 70, 780-791.
28. (c) Wang, G.; Kuroda, K.; Enoki, T.; Grosberg, A.; Masamune, S.; Oya, T.; Takeoka, Y.; Tanaka. T. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 9861-9864.
29. Hikmet, R. A. M.; Kemperman, H. Nature 1998, 392, 476-479.
30. (a) Wulff, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1812-1832.
31. (b) Steinke, J.; Sherrington, D. C.; Dunkin, I. R. Adv. Polym. Sci. 1995, 123, 81-125.
32. (c) Sellergren, B. Trends Anal. Chem. 1997, 16, 310-320.
33. (d) Takeuchi, T.; Haginaka, J. J. Chromatogr., B 1999, 728, 1-20.
34. (e) Whitcombe, M. J.; Alexander, C.; Vujfson, E. N. Synlett 2000, 911-923.
35. (f) Sellergren, B. Angew. Chem., Int. Ed. 2000, 39, 1031-1037.
36. (g) Haupt, K.; Mosbach, K. Chem. Rev. 2000, 100, 2495-2504.
37. (a) Watanabe, M.; Akahoshi, T.; Tabata, T.; Nakayama, D. J. Am. Chem. Soc. 1998, 120, 5577-5578.
38. (b) Miyata, T.; Asami, N.; Uragami, T. Nature 1999, 399, 766-769.
39. (c) Oya, T.; Enoli, T.; Grosberg, A. Y.; Masamune, S.; Sakiyama, T.; Takeoka, Y.; Tanaka, K.; Wang, G.; Yilmaz, Y.; Feld, M. S.; Dasari, R.; Tanaka, T. Science 1999, 286, 1543-1545.
40. (d) Kanekiyo, Y.; Sano, M.; Iguchi. R.; Shinkai, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1302-1310.
41. (e) Alvarez-Lorenzo, C.; Guney, O.; Oya, T.; Sakai, Y.; Kobayashi, M.; Enoki, T.; Takeoka, Y.; Ishibashi, T.; Kuroda, K.; Tanaka, K.; Wang, G.; Grosberg, A. Y.; Masamune, S.; Tanaka, T. Macromolecules 2000, 33, 8693-8697.
42. (a) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597.
43. (b) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359.
44. Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451.
45. Saito, M. A.; Onouchi, H.; Maeda, K.; Yashima, E. Macromolecules 2000, 33, 4616-4618.
46. Haung, H.; Kowalewski, T.; Remsen, E. E.; Gerzmann, R.; Wooley, K. L. J. Am. Chem. Soc. 1997, 119, 11653-11659.
47. (a) Kong, X.; Lam, J. W. Y.; Tang, B. Z. Macromolecules 1999, 32, 1722-1730.
48. (b) Karim, S. M. A.; Nomura, R.; Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3130-3136.
49. (a) Shirakawa, H.; Ito, T.; Ikeda, S. Polym. J. 1973, 4, 469-462.
50. (b) Harada, I.; Tasumi, M.; Shirakawa, H.; Ikeda, S. Chem. Lett. 1978, 1411-1414.
51. (c) Tabata, M.; Inaba, Y.; Yokota, K.; Nozaki, Y. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 465-475.
52. (d) Tabata, M.; Tanaka, Y.; Sadahiro, Y.; Sone, T.; Yokota, K.; Miura, I. Macromolecules 1997, 30, 5200-5204.
53. (e) Maeda, K.; Goto, H.; Yashima, E. Macromolecules 2001, 34, 1160-1164.
54. It is necessary to observe the measured laser Raman spectra of the solid poly(phenylacetylene) samples because they may deteriorate or isomerize from the cis to trans form in the presence of a strong laser light; in addition, the S/N ratio becomes worse due to the fluorescence when the exposure time is too long.
55. (a) Simionescu, C.; Percec, V. J. Polym. Sci., Polym. Symp. 1980, 67, 43-71.
56. (b) Furlani, A.; Napoletano, C.; Russo, M. V.; Feast, W. J. Polym. Bull. 1986, 16, 311-317.
57. (c) Yashima, E.; Huang, S.; Matsushima, T.; Okamoto, Y. Macromolecules 1995, 28, 4184-4193.
58. (d) Tang, B. Z.; Poon, W. H.; Leung, S. M.; Leung, W. H.; Peng, H. Macromolecules 1997, 30, 2209-2212.
59. (e) Fujita, Y.; Misumi, Y.; Tabata, M.; Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 3157-3163.
60. (f) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Kainosho, M.; Ono, A.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1999, 121, 12035-12044.
61. (g) Sone, T.; Asako, R.; Masuda, T.; Tabata, T.; Wada, T.; Sasabe, H. Macromolecules 2001, 34, 1586-1592.
62. (h) Shinohara, K.; Aoki, T.; Kaneko, T. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 1689-1697.
63. One may expect that the helicity induction in the gels may lead to deswelling of the gels, because the end-to-end distance of a polymer chain between cross-linking points seems to decrease by helix formation with chiral amines in DMSO. However, recent viscometric studies on a conformational change of poly((4-carboxyphenyl)acetylene) (poly-1-H) in DMSO before and after complexation with an optically active amine (-9) indicate that poly-1-H behaves as a weak polyelectrolyte in the presence of the amine; the poly-1-H-(R)-9 complex partly dissociates into carboxylate and ammonium ions. This feature might cause swelling of the gels because of repulsive electrostatic interactions between the carboxylate ions. Another important result obtained from the viscometric study is that the chain stiffness parameter (the persistent length) of poly-1-H in DMSO becomes longer in the presence of the chiral amine, from 4.2 nm in pure DMSO to 8.6 nm in DMSO with (R)-9. This means that the polymer becomes stiff, but the change in the poly-1-H conformation upon complexation with the amine is not as drastic as the coil to helix transition of polypeptides (Sato, T.; Ashida, Y.; Morino, K.; Maeda, K.; Okamoto, Y.; Yashima, E., unpublished results). On the basis of these results, we think that the helicity induction may not lead to a drastic change of the swelling ratio of the gels, but the formation of carboxylate ions may be responsible for the swelling behavior of the gels in the presence of chiral amines. However, it is not clear at present why the less bulky amino alcohol (8) and primary amines (9-11) prevent swelling or caused shrinking of the gels in DMSO.
64. (a) Park, T. G.; Hoffman, A. S. Macromolecules 1993, 26, 5045-5048.
65. (b) Kawasaki, H.; Sasaki, S.; Maeda, H.; Mihara, S.; Tokita, M.; Komai, T. J. Phys. Chem. 1996, 100, 16282-16284.
66. (a) Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800-9801,
67. (b) Kawamura, H.; Maeda, K.; Okamoto, Y.; Yashima, E. Chem. Lett. 2001, 58-59.
68. Onouchi, H.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2001, 123, 7441-7442.
69. (a) Yashima, E.; Maeda, Y.; Matsushima, T.; Okamoto, Y. Chirality 1997, 9, 593-600.
70. (b) Maeda, K.; Okada, S.; Yashima, E.; Okamoto, Y. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3180-3189.
71. (a) Maeda, K.; Yamamoto, N.; Okamoto, Y. Macromolecules 1998, 31, 5924-5926.
72. (b) Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122, 7813-7814.
73. (c) Ishikawa, M.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2002, 124, 7448-7458.
74. (a) Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895-8896.
75. (b) Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160.
76. When achiral amines, for instance, 2-aminoethanol and n-butylamine, were added to the optically active gels in DMSO induced by -5, the gels shrunk and became turbid, so that the CD measurements of the gels were difficult. We believe that an appropriate combination of chiral and achiral amines should make it possible to memorize the induced helicity in the gels.