Helicity induction and memory of the macromolecular helicity in a polyacetylene bearing a biphenyl pendant

Chemistry - An Asian Journal

Volumn 3, Issue 3, 2008, Pages 614-624

  Maeda, Katsuhiro ^a   Tamaki, Shinji ^a   Tamura, Kazumi ^a   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Biaryls; Chiral memory; Chirality; Helical structures; Poly(phenylacetylene)

Indexed keywords

EID: 54549083237     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200700279     Document Type: Article

References (160)

1. For recent reviews on the detection of chirality, see: a) S. Shinkai, M. Ikeda, A. Sugasaki, M. Takeuchi, Acc. Chem. Res. 2001, 34, 494-503;
2. b) J. W. Canary, A. E. Holmes, J. Liu, Enantiomer 2001, 6, 181-188;
3. c) T. Kurtán, N. Nesnas, Y. Q. Li, X. F. Huang, K. Nakanishi, N. Berova, J. Am. Chem. Soc. 2001, 123, 5962-5973;
4. d) H. Tsukube, S. Shinoda, Chem. Rev. 2002, 102, 2389-2403;
5. e) E. Yashima, Anal. Sci. 2002, 18, 3-6;
6. f) S. Allenmark, Chirality 2003, 15, 409-422;
7. g) V. V. Borovkov, G. A. Hembury, Y. Inoue, Acc. Chem. Res. 2004, 37, 449-459;
8. h) M. A. Mateos-Timoneda, M. Crego-Calama, D. N. Reinhoudt, Chem. Soc. Rev. 2004, 33, 363-372;
9. i) E. Yashima, K. Maeda, T. Nishimura, Chem. Eur. J. 2004, 10, 43-51;
10. j) K. Maeda, E. Yashima, Top. Curr. Chem. 2006, 265, 47-88, and references therein;
11. for recent examples of the detection of chirality by supramolecular chirality induction, see: k) X. Hung, B. H. Rickman, B. Borhan, N. Berova, K. Nakanishi, J. Am. Chem. Soc. 1998, 120, 6185-6186;
12. l) T. Mizutani, S. Yagi, T. Morinaga, T. Nomura, T. Takagishi, S. Kitagawa, H. Ogoshi, J. Am. Chem. Soc. 1999, 121, 754-759;
13. m) Y. Mizuno, T. Aida, K. Yamaguchi, J. Am. Chem. Soc. 2000, 122, 5278-5285;
14. n) H. Nakashima, J. R. Kobe, K. Torimitsu, M. Fujiki, J. Am. Chem. Soc. 2001, 123, 4847-4848;
15. o) H. Fenniri, B. L. Deng, A. E. Ribbe, J. Am. Chem. Soc. 2002, 124, 11 064-11072;
16. p) J. M. Lintuluoto, K. Nakayama, J. Setsune, Chem. Commun. 2006, 3492-3494;
17. q) J. Aimi, K. Oya, A. Tsuda, T. Aida, Angew. Chem. 2007, 119, 2077-2081;
18. Angew. Chem. Int. Ed. 2007, 46, 2031-2035.
19. For reviews on chiral amplification by helical polymers, see reference [1i,j] and: a) M. M. Green, N. C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science 1995, 268, 1860-1866;
20. b) J. J. L. M. Cornelissen, A. E. Rowan, R. J. M. Nolte, N. A. J. M. Sommerdijk, Chem. Rev. 2001, 101, 4039-4070;
21. c) T. Nakano, Y. Okamoto, Chem. Rev. 2001, 101, 4013-4038;
22. d) M. Fujiki, Macromol. Rapid Commun. 2001, 22, 539-563;
23. e) R. Nomura, H. Nakako, T. Masuda, J. Mol. Catal. A 2002, 190, 197-205;
24. f) J. W. Y. Lam, B. Z. Tang, Acc. Chem. Res. 2005, 38, 745-754;
25. g) D. B. Amabilino, J.-L. Serrano, T. Sierra, J. Veciana, J. Polym. Sci. Part A: Polym. Chem. 2006, 44, 3161-3174;
26. for recent examples of chiral amplification by supramolecular helical assemblies, see: h) J. H. K. K. Hirschberg, L. Brunsveld, A. Ramzi, J. A. J. M. Vekemans, R. P. Sijbesma, E. W. Meijer, Nature 2000, 407, 167-170;
27. i) L. Brunsveld, E. W. Meijer, R. B. Prince, J. S. Moore, J. Am. Chem. Soc. 2001, 123, 7978-7984;
28. j) L. J. Prins, P. Timmerman, D. N. Reinhoudt, J. Am. Chem. Soc. 2001, 123, 10 153-10163;
29. k) L. van Gestel, A. R. A. Palmans, B. Titulaer, J. A. J. M. Vekemans, E. W. Meijer, J. Am. Chem. Soc. 2005, 127, 5490-5494;
30. l) V. Percec, A. S. E. Dulcey, M. Peterca, M. Ilies, J. Ladislaw, B. M. Rosen, U. Edlund, P. A. Heiney, Angew. Chem. 2005, 117, 6674-6679;
31. Angew. Chem. Int. Ed. 2005, 44, 6516-6521;
32. m) W. Jin, T. Fukushima, M. Niki, A. Kosaka, N. Ishii, T. Aida, Proc. Natl. Acad. Sci. USA 2005, 102, 10 801-10806;
33. n) J. J. D. de Jong, T. D. Tiemersma-Wegman, J. H. van Esch, B. L. Feringa, J. Am. Chem. Soc. 2005, 127, 13804-13805;
34. o) A. Ajayaghosh, R. Varghese, S. Mahesh, V. K. Praveen, Angew. Chem. 2006, 118, 7893-7896;
35. Angew. Chem. Int. Ed. 2006, 45, 7729-7732;
36. p) E. Yashima, K. Maeda in Foldamers (Eds.: H. Stefan, I. Huc), Wiley-VCH, Weinheim, 2007, chap. 11.
37. Reviews: a) Y. Okamoto, T. Nakano, Chem. Rev. 1994, 94, 349-372;
38. b) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 2001, 101, 3893-4011;
39. c) Y. Okamoto, E. Yashima, Angew. Chem. 1998, 110, 1072-1095;
40. Angew. Chem. Int. Ed. 1998, 37, 1020-1043;
41. d) E. Yashima, C. Yamamoto, Y. Okamoto, Synlett 1998, 344-360;
42. e) T. Nakano, J. Chromatogr. A 2001, 906, 205-225;
43. f) M. Reggelin, S. Doerr, M. Klussmann, M. Schultz, M. Hobbach, Proc. Natl. Acad. Sci. USA 2004, 101, 5461-5466.
44. a) E. Yashima, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1995, 117, 11596-11597;
45. b) E. Yashima, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1997, 119, 6345-6359.
46. For examples of polyacetylenes, see: a) E. Yashima, T. Nimura, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1996, 118, 9800-9801;
47. b) E. Yashima, Y. Maeda, Y. Okamoto, Chem. Lett. 1996, 955-956;
48. c) E. Yashima, Y. Maeda, T. Matsushima, Y. Okamoto, Chirality 1997, 9, 593-600;
49. d) E. Yashima, H. Goto, Y. Okamoto, Polym. J. 1998, 30, 69-71;
50. e) H. Kawamura, K. Maeda, Y. Okamoto, E. Yashima, Chem. Lett. 2001, 58-59;
51. f) H. Onouchi, K. Maeda, E. Yashima, J. Am. Chem. Soc. 2001, 123, 7441-7442;
52. g) K. Maeda, S. Okada, E. Yashima, Y. Okamoto, J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 3180-3189;
53. h) R. Nonokawa, E. Yashima, J. Am. Chem. Soc. 2003, 125, 1278-1283;
54. i) J. Tabei, R. Nomura, F. Sanda, T. Masuda, Macromolecules 2003, 36, 8603-8608;
55. j) K. Morino, N. Watase, K. Maeda, E. Yashima, Chem. Eur. J. 2004, 10, 4703-4707;
56. k) H. Onouchi, D. Kashiwagi, K. Hayashi, K. Maeda, E. Yashima, Macromolecules 2004, 37, 5495-5503;
57. l) K. Nagai, K. Maeda, Y. Takeyama, K. Sakajiri, E. Yashima, Macromolecules 2005, 38, 5444-5451;
58. m) H. Onouchi, T. Hasegawa, D. Kashiwagi, H. Ishiguro, K. Maeda, E. Yashima, Macromolecules 2005, 38, 8625-8633;
59. n) R. Kakuchi, R. Sakai, I. Otsuka, T. Satoh, H. Kaga, T. Kakuchi, Macromolecules 2005, 38, 9441-9447;
60. o) T. Hasegawa, K. Maeda, H. Ishiguro, E. Yashima, Polym. J. 2006, 38, 912-919;
61. p) R. Sakai, I. Otsuka, T. Satoh, R. Kakuchi, H. Kaga, T. Kakuchi, Macromolecules 2006, 39, 4032-4037.
62. For examples of other induced helical polymers and oligomers, see: a) M. M. Green, C. Khatri, N. C. Peterson, J. Am. Chem. Soc. 1993, 115, 4941-4942;
63. b) D. S. Schlitzer, B. M. Novak, J. Am. Chem. Soc. 1998, 120, 2196-2197;
64. c) I. D. Norris, L. A. P. Kane-Maguire, G. G. Wallace, Macromolecules 1998, 31, 6529-6533;
65. d) K. Maeda, N. Yamamoto, Y. Okamoto, Macromolecules 1998, 31, 5924-5926;
66. e) E. Yashima, K. Maeda, T. Yamanaka, J. Am. Chem. Soc. 2000, 122, 7813-7814;
67. f) Y. Inai, K. Tagawa, A. Takasu, T. Hirabayashi, T. Oshikawa, M. Yamashita, J. Am. Chem. Soc. 2000, 122, 11731-11732;
68. g) Y. Inai, Y. Ishida, K. Tagawa, A. Takasu, T. Hirabayashi, J. Am. Chem. Soc. 2002, 124, 2466-2473;
69. h) M. Ishikawa, K. Maeda, E. Yashima, J. Am. Chem. Soc. 2002, 124, 7448-7458;
70. i) P. Dellaportas, R. G. Jones, S. J. Holder, Macromol. Rapid Commun. 2002, 23, 99-103;
71. j) R. Sakai, T. Satoh, R. Kakuchi, H. Kaga, T. Kakuchi, Macromolecules 2003, 36, 3709-3713;
72. k) M. Ishikawa, K. Maeda, Y. Mitsutsuji, E. Yashima, J. Am. Chem. Soc. 2004, 126, 732-733;
73. l) L. Arnt, G. N. Tew, Macromolecules 2004, 37, 1283-1288;
74. m) R. Sakai, T. Satoh, R. Kakuchi, H. Kaga, T. Kakuchi, Macromolecules 2004, 37, 3996-4003;
75. n) K. P. R. Nilsson, J. Rydberg, L. Baltzer, O. Ingan Us, Proc. Natl. Acad. Sci. USA 2004, 101, 11197-11 202;
76. o) K. Maeda, K. Morioka, E. Yashima, Macromolecules 2007, 40, 1349-1352.
77. For examples of guest-induced preferred-handed helix formation of foldamers, see reference [3b] and: a) R. B. Prince, S. A. Barnes, J. S. Moore, J. Am. Chem. Soc. 2000, 122, 2758-2762;
78. b) A. Tanatani, M. J. Mio, J. S. Moore, J. Am. Chem. Soc. 2001, 123, 1792-1793;
79. c) M. Inouye, M. Waki, H. Abe, J. Am. Chem. Soc. 2004, 126, 2022-2027;
80. d) A. Petitjean, H. Nierengarten, A. van Dorsselaer, J. M. Lehn, Angew. Chem. 2004, 116, 3781-3785;
81. Angew. Chem. Int. Ed. 2004, 43, 3695-3699;
82. e) J. L. Hou, X. B. Shao, G. J. Chen, Y. X. Zhou, X. K. Jiang, Z. T. Li, J. Am. Chem. Soc. 2004, 126, 12386-12394;
83. f) V. Maurizot, C. Dolain, I. Huc, Eur. J. Org. Chem. 2005, 1293-1301;
84. g) C. Ikeda, Z. S. Yoon, M. Park, H. Inoue, D. Kim, A. Osuka, J. Am. Chem. Soc. 2005, 127, 534-535;
85. h) M. Waki, H. Abe, M. Inouye, Chem. Eur. J. 2006, 12, 7839-7847.
86. a) E. Yashima, K. Maeda, Y. Okamoto, Nature 1999, 399, 449-451;
87. b) K. Maeda, K. Morino, Y. Okamoto, T. Sato, E. Yashima, J. Am. Chem. Soc. 2004, 126, 4329-4342.
88. a) M. Eyer, K. Schlögl, R. Schölm, Tetrahedron 1981, 37, 4239-4244;
89. b) S. Hosoi, M. Kamiya, F. Kikuchi, T. Ohta, Tetrahedron Lett. 2001, 42, 6315-6317;
90. c) S. Superchi, R. Bisaccia, D. Casarini, A. Laurita, C. Rosini, J. Am. Chem. Soc. 2006, 128, 6893-6902.
91. a) M. P. Reidy, M. M. Green, Macromolecules 1990, 23, 4225-4234;
92. b) M. Sisido, M. P. Reidy, M. M. Green, Macromolecules 1991, 24, 6860-6862;
93. c) J.-P. Mazaleyrat, K. Wright, A. Gaucher, N. Toulemonde, M. Wakselman, S. Oancea, C. Peggion, F. Formaggio, V. Setnicka, T. A. Keiderling, C. Toniolo, J. Am. Chem. Soc. 2004, 126, 12874-12879;
94. d) J.-P. Mazaleyrat, K. Wright, A. Gaucher, N. Toulemonde, L. Dutot, M. Wakselman, Q. B. Broxterman, B. Kaptein, S. Oancea, C. Peggion, M. Crisma, F. Formaggio, C. Toniolo, Chem. Eur. J. 2005, 11, 6921-6929;
95. e) S. Reichert, B. Breit, Org. Lett. 2007, 9, 899-902.
96. a) T. Mizutani, H. Takagi, O. Hara, T. Horiguchi, H. Ogoshi, Tetrahedron Lett. 1997, 38, 1991-1994;
97. b) Y. Kubo, T. Ohno, J. Yamanaka, S. Tokita, T. Iida, Y. Ishimaru, J. Am. Chem. Soc. 2001, 123, 12700-12701;
98. c) T. Hayashi, T. Aya, M. Nonoguchi, T. Mizutani, Y. Hisaeda, S. Kitagawa, H. Ogoshi, Tetrahedron 2002, 58, 2803-2811;
99. d) R. Eelkema, B. L. Feringa, J. Am. Chem. Soc. 2005, 127, 13480-13481;
100. e) H. Takagi, T. Mizutani, T. Horiguchi, S. Kitagawa, H. Ogoshi, Org. Biomol. Chem. 2005, 3, 2091-2094;
101. f) K. Morioka, N. Tamagawa, K. Maeda, E. Yashima, Chem. Lett. 2006, 35, 110-111;
102. g) Y. Ishii, Y. Onda, Y. Kubo, Tetrahedron Lett. 2006, 47, 8221-8225;
103. h) R. Eelkema, B. L. Feringa, Org. Lett. 2006, 8, 1331-1334.
104. a) K. Mikami, M. Yamanaka, Chem. Rev. 2003, 103, 3369-3400;
105. b) P. J. Walsh, A. E. Lurain, J. Balsells, Chem. Rev. 2003, 103, 3297-3344.
106. [14]
107. a) K. Maeda, Y. Takeyama, K. Sakajiri, E. Yashima, J. Am. Chem. Soc. 2004, 126, 16284-16285;
108. b) K. Nagai, K. Sakajiri, K. Maeda, K. Okoshi, T. Sato, E. Yashima, Macromolecules 2006, 39, 5371-5380.
109. For the effect of chirality memory in supramolecular chemistry, see references [1m] and [11b] and: a) Y. Furusho, T. Kimura, Y. Mizuno, T. Aida, J. Am. Chem. Soc. 1997, 119, 5267-5268;
110. b) A. Sugasaki, M. Ikeda, M. Takeuchi, A. Robertson, S. Shinkai, J. Chem. Soc. Perkin Trans. 1 1999, 3259-3264;
111. c) L. J. Prins, F. de Jong, P. Timmerman, D. N. Reinhoudt, Nature 2000, 408, 181-184;
112. d) R. Lauceri, A. Raudino, L. M. Scolaro, N. Micali, R. Purrello, J. Am. Chem. Soc. 2002, 124, 894-895;
113. e) T. Ishi-i, M. Crego-Calama, P. Timmerman, D. N. Reinhoudt, S. Shinkai, J. Am. Chem. Soc. 2002, 124, 14 631-14 641;
114. for the effect of macromolecular helicity memory, see references [5k, o] and [8] and: f) T. Miyagawa, A. Furuko, K. Maeda, H. Katagiri, Y. Furusho, E. Yashima, J. Am. Chem. Soc. 2005, 127, 5018-5019;
115. g) T. Hasegawa, K. Morino, Y. Tanaka, H. Katagiri, Y. Furusho, E. Yashima, Macromolecules 2006, 39, 482-488;
116. for reviews of the effect of chiral memory, see reference [1h, j] and: h) R. Purrello, Nat. Mater. 2003, 2, 216-217.
117. a) C. I. Simionescu, V. Percec, S. Dumitrescu, J. Polym. Sci: Polym. Chem. Ed. 1977, 15, 2497-2509;
118. b) C. I. Simionescu, V. Percec, Prog. Polym. Sci. 1982, 8, 133-214;
119. c) A. Furlani, C. Napoletano, M. V. Russo, W. J. Feast, Polym. Bull. 1986, 16, 311-317;
120. d) S. Matsunami, T. Kakuchi, F. Ishii, Macromolecules 1997, 30, 1074-1078;
121. e) Y. Kishimoto, P. Eckerle, T. Miyatake, M. Kainosho, A. Ono, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1999, 121, 12035-12044;
122. f) V. Percec, J. G. Rudick, M. Peterca, M. Wagner, M. Obata, C. M. Mitchell, W.-D. Cho, V. S. K. Balagurusamy, P. A. Heiney, J. Am. Chem. Soc. 2005, 127, 15 257-15 264;
123. g) S.-i. Sakurai, K. Okoshi, J. Kumaki, E. Yashima, Angew. Chem. 2006, 118, 1267-1270;
124. Angew. Chem. Int. Ed. 2006, 45, 1245-1248;
125. h) S.-i. Sakurai, K. Okoshi, J. Kumaki, E. Yashima, J. Am. Chem. Soc. 2006, 128, 5650-5651.
126. Some complexes showed a slight increase in CD intensity with time that reached a constant value after a few days. Therefore, the CD spectra of poly-1 with chiral amines and amino alcohols were recorded in DMSO after standing of the samples at room temperature for 5 days (2-6, 8, 10, and 11) and 14 days (7 and 9) (Table 1).
127. For leading references of helicity inversion by achiral stimuli, see references [1i, j] and [2a-f] and: a) Y. Okamoto, T. Nakano, E. Ono, K. Hatada, Chem. Lett. 1991, 525-528;
128. b) G. Maxein, R. Zentel, Macromolecules 1995, 28, 8438-8440;
129. c) K. Maeda, Y. Okamoto, Macromolecules 1998, 31, 5164-5166;
130. d) K. S. Cheon, J. V. Selinger, M. M. Green, Angew. Chem. 2000, 112, 1542-1545;
131. Angew. Chem. Int. Ed. 2000, 39, 1482-1485;
132. e) M. Fujiki, J. R. Koe, M. Motonaga, H. Nakashima, K. Terao, A. Teramoto, J. Am. Chem. Soc. 2001, 123, 6253-6261;
133. f) H. Nakako, R. Nomura, T. Masuda, Macromolecules 2001, 34, 1496-1502;
134. g) K. K. L. Cheuk, J. W. Y. Lam, J. Chen, L. M. Lai, B. Z. Tang, Macromolecules 2003, 36, 5947-5959;
135. h) K. Maeda, K. Morino, E. Yashima, J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 3625-3631;
136. i) K. K. L. Cheuk, J.W. Y. Lam, L. M. Lai, Y. P. Dong, B. Z. Tang, Macromolecules 2003, 36, 9752-9762;
137. j) K. Maeda, N. Kamiya, E. Yashima, Chem. Eur. J. 2004, 10, 4000-4010;
138. k) F. Sanda, K. Terada, T. Masuda, Macromolecules 2005, 38, 8149-8154;
139. l) I. Otsuka, R. Sakai, T. Satoh, R. Kakuchi, H. Kaga, T. Kakuchi, J. Polym. Sci. Part A: Polym. Chem. 2005, 43, 5855-5863;
140. for helicity inversion by chiral stimuli, see: m) E. Yashima, Y. Maeda, Y. Okamoto, J. Am. Chem. Soc. 1998, 120, 8895-8896;
141. n) E. Yashima, K. Maeda, O. Sato, J. Am. Chem. Soc. 2001, 123, 8159-8160;
142. o) K. Morino, K. Maeda, E. Yashima, Macromolecules 2003, 36, 1480-1486;
143. p) K. Maeda, H. Mochizuki, M. Watanabe, E. Yashima, J. Am. Chem. Soc. 2006, 128, 7639-7650.
144. G. Lindsten, O. Wennerström, R. Isaksson, J. Org. Chem. 1987, 52, 547-554.
145. helix), see Supporting Information, Figure S3. A slight difference in the CD spectral pattern above 420 nm observed for some complexes may be ascribed to a small difference in the helical conformations of poly-1.
146. [19]
147. Structurally similar chiral amino alcohols, such as (R)-8 and (S)-9, did not show such a time-dependent inversion of the helix sense, and the complexes exhibited the same CD pattern even after heating at 80°C. The reason is not clear at present, but a delicate balance in the bulkiness of the substituents of the amino alcohols may be important for the time-dependent inversion of the helix, as observed for the poly-1-(R)-7 system.
148. For reviews, see: a) T. Masuda, T. Higashimura, Adv. Polym. Sci. 1987, 81, 121-165;
149. b) H. Shirakawa, T. Masuda, K. Takeda in The Chemistry of Triple-Bond Functional Groups (Ed.: S. Patai), John Wiley & Sons, New York, 1994, chap. 17.
150. Recently, Novak and co-workers reported that an optically active polyguanidine prepared by the helix-sense-selective polymerization of an achiral carbodiimide bearing a bulky anthracene pendant with a chiral titanium complex exhibited a reversible temperature-and solvent-induced chiroptical switch due to a change in the orientation of the pendant anthracene rings, as evidenced by vibrational CD measurements, but the main-chain helicity remained unchanged; see: a) H. Z. Tang, B. M. Novak, J. He, P. L. Polavarapu, Angew. Chem. 2005, 117, 7464-7467;
151. Angew. Chem. Int. Ed. 2005, 44, 7298-7301;
152. b) H. Z. Tang, P. D. Boyle, B. M. Novak, J. Am. Chem. Soc. 2005, 127, 2136-2142.
153. The memory of the macromolecular helicity and the axial chirality in the biphenyl units of poly-1 assisted by achiral 13 also lasted for a long time (see Supporting Information, Figure S7B).
154. a) T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594;
155. Angew. Chem. Int. Ed. 2004, 43, 1566-1568;
156. b) D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357.
157. a) H. Shirakawa, T. Ito, S. Ikeda, Polym. J. 1973, 4, 469-472;
158. b) M. Tabata, Y. Tanaka, Y. Sadahiro, T. Sone, K. Yokota, I. Miura, Macromolecules 1997, 30, 5200-5204;
159. c) K. Maeda, H. Goto, E. Yashima, Macromolecules 2001, 34, 1160-1164.
160. N. Hashimoto, T. Aoyama, T. Shioiri, Chem. Pharm. Bull. 1981, 29, 1475-1478.