Enantioselective adsorption of chiral amines on an induced helical poly(bis(4-carboxyphenoxy)phosphazene): Chiral filter effect

Macromolecules

Volumn 44, Issue 8, 2011, Pages 2457-2464

  Maeda, Katsuhiro ^a,b   Kuroyanagi, Kenji ^a   Sakurai, Shin Ichiro ^a   Yamanaka, Toshio ^a   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1-PHENYLETHYLAMINE; CHIRAL AMINES; CHIRAL FILTERS; COMPLEX SOLUTION; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE ADSORPTION; EQUIMOLAR AMOUNT; HELICAL STRUCTURES; OPTICAL ACTIVITY; OPTICALLY ACTIVE; PHOSPHAZENES;

ADSORPTION; OPTICAL ROTATION;

ENANTIOMERS;

EID: 79955002700     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma200411g     Document Type: Article

References (81)

1. Green, M. M.; Peterson, N. C.; Sato, T.; Teramoto, A.; Cook, R.; Lifson, S. Science 1995, 268, 1860-1866
2. 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
3. Fujiki, M. Macromol. Rapid Commun. 2001, 22, 539-563
4. Fujiki, M. Chem. Rec. 2009, 9, 271-298
5. Suginome, M.; Ito, Y. Adv. Polym. Sci. 2004, 17, 77-136
6. Amabilino, D. B.; Serrano, J.-L.; Sierra, T.; Veciana, J. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 3161-3174
7. Otten, M. B. J.; Metselaar, G. A.; Cornelissen, J. J. L. M.; Rown, A. E.; Nolte, R. J. M. In Foldamers: Structure, Properties, and Applications; Hecht, S.; Huc, I., Eds.; Wiley-VCH: Weinheim, 2007.
8. Schwartz, E.; Koepf, M.; Kitto, H. J.; Nolte, R. J. M.; Rowan, A. E. Polym. Chem. 2011, 2, 33-47
9. Schlitzer, D. S.; Novak, B. M. J. Am. Chem. Soc. 1998, 120, 2196-2197
10. Tang, H. Z.; Boyle, P. D.; Novak, B. M. J. Am. Chem. Soc. 2005, 127, 2136-2142
11. Nomura, R.; Nakako, H.; Masuda, T. J. Mol. Catal. A: Chem. 2002, 190, 197-205
12. Lam, J. W. Y.; Tang, B. Z. Acc. Chem. Res. 2005, 38, 745-754
13. Rudick, J. G.; Percec, V. New J. Chem. 2007, 31, 1083-1096
14. Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 165-180
15. Yashima, E.; Maeda, K.; Furusho, Y. Acc. Chem. Res. 2008, 41, 1166-1180
16. Rudick, J. G.; Percec, V. Acc. Chem. Res. 2008, 41, 1641-1652
17. Liu, J.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2009, 109, 5799-5867
18. Yashima, E.; Maeda, K.; Nishimura, T. Chem.-Eur. J. 2004, 10, 43-51
19. Palmans, A. R. A.; Meijer, E. W. Angew. Chem., Int. Ed. 2007, 46, 8948-8968
20. Pijper, D.; Feringa, B. L. Soft Matter 2008, 4, 1349-1372
21. Yashima, E.; Maeda, K. Macromolecules 2008, 41, 3-12
22. Yashima, E.; Maeda, K.; Okamoto, Y. Nature 1999, 399, 449-451
23. Onouchi, H.; Kashiwagi, D.; Hayashi, K.; Maeda, K.; Yashima, E. Macromolecules 2004, 37, 5495-5503
24. Maeda, K.; Morino, K.; Okamoto, Y.; Sato, T.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 4329-4342
25. Ishikawa, M.; Maeda, K.; Mitsutsuji, Y.; Yashima, E. J. Am. Chem. Soc. 2004, 126, 732-733
26. Miyagawa, T.; Furuko, A.; Maeda, K.; Katagiri, H.; Furusho, Y.; Yashima, E. J. Am. Chem. Soc. 2005, 127, 5018-5019
27. Miyagawa, T.; Yamamoto, M.; Muraki, R.; Onouchi, H.; Yashima, E. J. Am. Chem. Soc. 2007, 129, 3676-3682
28. Kawauchi, T.; Kumaki, J.; Kitaura, A.; Okoshi, K.; Kusanagi, H.; Kobayashi, K.; Sugai, T.; Shinohara, H.; Yashima, E. Angew. Chem., Int. Ed. 2008, 47, 515-519
29. Kawauchi, T.; Kitaura, A.; Kumaki, J.; Kusanagi, H.; Yashima, E. J. Am. Chem. Soc. 2008, 130, 11889-11891
30. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1995, 117, 11596-11597
31. Yashima, E.; Nimura, T.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1996, 118, 9800-9801
32. Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345-6359
33. Yashima, E.; Maeda, Y.; Matsushima, T.; Okamoto, Y. Chirality 1997, 9, 593-600
34. Yashima, E.; Goto, H.; Okamoto, Y. Polym. J. 1998, 30, 69-71
35. Onouchi, H.; Maeda, K.; Yashima, E. J. Am. Chem. Soc. 2001, 123, 7441-7442
36. Nonokawa, R.; Yashima, E. J. Am. Chem. Soc. 2003, 125, 1278-1283
37. Nakashima, H.; Koe, J. R.; Torimitsu, K.; Fujiki, M. J. Am. Chem. Soc. 2001, 123, 4847-4848
38. Tabei, J.; Nomura, R.; Sanda, F.; Masuda, T. Macromolecules 2003, 36, 8603-8608
39. Nagai, K.; Maeda, K.; Takeyama, Y.; Sakajiri, K.; Yashima, E. Macromolecules 2005, 38, 5444-5451
40. Sakai, R.; Satoh, T.; Kakuchi, R.; Kaga, H.; Kakuchi, T. Macromolecules 2003, 36, 3709-3713
41. Sakai, R.; Otsuka, I.; Satoh, T.; Kakuchi, R.; Kaga, H.; Kakuchi, T. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 325-334
42. Nolte, R. J. M.; Van Beijnen, A. J. M.; Drenth, W. J. Am. Chem. Soc. 1974, 96, 5932-5933
43. Yashima, E.; Huang, S.; Okamoto, Y. J. Chem. Soc., Chem. Commun. 1994, 1811-1812
44. Yashima, E.; Matsushima, T.; Nimura, T.; Okamoto, Y. Korea Polym. J. 1996, 4, 139-146
45. Yashima, E.; Maeda, K.; Sato, O. J. Am. Chem. Soc. 2001, 123, 8159-8160
46. Nakano, T. J. Chromatogr. A 2001, 906, 205-225
47. Okamoto, Y.; Yashima, E. Angew. Chem., Int. Ed. 1998, 37, 1020-1043
48. Tsuchida, A.; Hasegawa, T.; Kobayashi, K.; Yamamoto, C.; Okamoto, Y. Bull. Chem. Soc. Jpn. 2002, 75, 2681-2685
49. Aoki, T.; Kaneko, T. Polym. J. 2005, 37, 717-735
50. Maeda, K.; Mochizuki, H.; Watanabe, M.; Yashima, E. J. Am. Chem. Soc. 2006, 128, 7639-7650
51. Liu, R. Y.; Sanda, F.; Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 4175-4182
52. Kawauchi, T.; Kitaura, A.; Kawauchi, M.; Takeichi, T.; Kumaki, J.; Iida, H.; Yashima, E. J. Am. Chem. Soc. 2010, 132, 12191-12193
53. Yashima, E.; Maeda, Y.; Okamoto, Y. Polym. J. 1999, 31, 1033-1036
54. Reggelin, M.; Doerr, S.; Klussmann, M.; Schultz, M.; Holbach, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5461-5466
55. Sanda, F.; Araki, H.; Masuda, T. Chem. Lett. 2005, 34, 1642-1643
56. Miyabe, T.; Hase, Y.; Iida, H.; Maeda, K.; Yashima, E. Chirality 2009, 21, 44-50
57. Yamamoto, T.; Suginome, M. Angew. Chem., Int. Ed. 2009, 48, 539-542
58. For reviews on helical polymers, see: Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013-4038
59. Yashima, E.; Maeda, K.; Iida, H.; Furusho, Y.; Nagai, K. Chem. Rev. 2009, 109, 6102-6211
60. Yashima, E.; Maeda, K.; Yamanaka, T. J. Am. Chem. Soc. 2000, 122, 7813-7814
61. Allcock, H. R. Angew. Chem., Int. Ed. Engl. 1977, 16, 147-156
62. Mark, J. E.; Allcock, H. R.; West, R. Inorganic Polymers; Prentice Hall: Englewood Cliffs, NJ, 1992.
63. Manners, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 1602-1621
64. For optically active poly(organophosphazene)s, see: Allcock, H. R.; Fuller, T. J.; Mack, D. P.; Matsumura, K.; Smeltz, K. M. Macromolecules 1977, 10, 824-830
65. Allcock, H. R.; Fuller, T. J. Macromolecules 1980, 13, 1338-1345
66. Allcock, H. R.; Scopelianos, A. G. Macromolecules 1983, 16, 715-719
67. Allcock, H. R.; Pucher, S. R. Macromolecules 1991, 24, 23-34
68. Song, S.-C.; Lee, S. B.; Jin, J.; Sohn, Y. S. Macromolecules 1999, 32, 2188-2193 A helicoidal secondary structure has been proposed for poly(organophosphazene)s bearing an optically active binaphthyl group. See: Carriedo, G. A.; García-Alonso, F. J.; González, P. A.; García-Alvarez, J. L. Macromolecules 1998, 31, 3189-3196
69. Carriedo, G. A.; García Alvarez, J. L.; García Alonso, F. J.; Presa Soto, A.; Tarazona, M. P.; Mendicuti, F.; Marcelo, G. Macromolecules 2004, 37, 5437-5443
70. Carriedo, G. A.; García Alonso, F. J.; Presa Soto, A. Macromolecules 2006, 39, 4704-4709
71. Allcock, H. R.; Kwon, S. Macromolecules 1989, 22, 75-79
72. Allcock, H. R.; Crane, C. A.; Morrissey, C. T.; Nelson, J. M.; Reeves, S. D.; Honeyman, C. H.; Manners, I. Macromolecules 1996, 29, 7740-7747
73. Stewart, F. F.; Lash, R. P.; Singler, R. E. Macromolecules 1997, 30, 3229-3233
74. In the absence of 2, poly- 1L and poly- 1H showed a linear relationship in the Huggins plots, and the intrinsic viscosities ([η] (dL/g)) were 0.08 and 1.66, respectively.
75. A possibility that poly- 1 is a dynamic helical polymer consisting of right- and left-handed helical segments separated by helical reversals (1, 11) could not be completely excluded.
76. The viscosities of the poly- 1L - and poly- 1H -(R)- 2 complexes significantly decreased upon the addition of a small amount of the hydrochloric acid salt of (R)- 2 ([(R)- 2• HCl]/[carboxy residues of poly- 1 ] = 0.02) independent of the annealing process, indicating that the polymers are a weak polyelectrolyte in DMSO in the presence of the chiral amine.
77. Poly- 1L chains were too short to observe the morphology changes by AFM (see Figure S2).
78. n) of poly- 1H were estimated to be 61.4 nm and 1.6, respectively (Table 1).
79. Allcock, H. R.; Kugel, R. L.; Valan, K. J. Inorg. Chem. 1966, 5, 1709-1715
80. Allcock, H. R.; Kugel, R. L. Inorg. Chem. 1966, 5, 1716-1718
81. Sulkowski, W.; Sulkowski, A.; Makarucha, B.; Kireev, V. Eur. Polym. J. 2000, 36, 1519-1524