Helical arrays of pendant fullerenes on optically active poly(phenylacetylene)s

Chemistry - A European Journal

Volumn 11, Issue 4, 2005, Pages 1181-1190

  Nishimura, Tatsuya ^a   Maeda, Katsuhiro ^a   Ohsawa, Sousuke ^a   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Chirality; Circular dichroism; Fullerenes; Helical structures; Polymers

Indexed keywords

ARRAYS; CATALYSTS; COPOLYMERIZATION; FULLERENES; REACTION KINETICS; RHODIUM; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

HELICAL STRUCTURES; PENDANTS; PHENYLACETYLENE; SOLID SUBSTRATES;

ACETYLENE;

BENZYL DERIVATIVE; COPOLYMER; FULLERENE DERIVATIVE; GLYCINE DERIVATIVE; N (4 ETHYNYLBENZYL)GLYCINE; PHENYLACETYLENE; POLY(PHENYLACETYLENE) DERIVATIVE; POLYMER; RHODIUM; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; OPTICAL ROTATION; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 14544292445     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400812     Document Type: Article

References (103)

1. For reviews, see: a) M. Prato, J. Mater. Chem. 1997, 7, 1097-1109;
2. b) V. V. Tsukruk, Prog. Polym. Sci. 1997, 22, 247-311;
3. c) Y. Chen, Z. Huang, R. F. Cai, B. C. Yu, Eur. Polym. J. 1998, 34, 137-151;
4. d) M. Prato, M. Maggini, Acc. Chem. Res. 1998, 31, 519-526;
5. e) L. Dai, A. W. H. Mau, Adv. Mater. 2001, 13, 899-913;
6. f) A. Cravino, N. S. Sariciftci, J. Mater. Chem. 2002, 12, 1931-1943.
7. S. R. Wilson, D. I. Schuster, B. Nuber, M. S. Meier, M. Maggini, M. Prato, R. Taylor, Fullerenes: Chemistry, Physics, and Technology (Eds.; K. M. Kadish, R. S. Ruoff), Wiley, New York, 2000.
8. a) A. W. Jensen, S. R. Wilson, D. I. Schuster, Bioorg. Med. Chem. 1996, 4, 767-779;
9. b) A. M. Cassell, W. A. Scrivens, J. M. Tour, Angew. Chem. 1998, 110, 1670-1672; Angew. Chem. Int. Ed. 1998, 37, 1528-1531;
10. b) A. M. Cassell, W. A. Scrivens, J. M. Tour, Angew. Chem. 1998, 110, 1670-1672; Angew. Chem. Int. Ed. 1998, 37, 1528-1531;
11. c) E. Nakamura, H. Isobe, N. Tomita, M. Sawamura, S. Jinno, H. Okayama, Angew. Chem. 2000, 112, 4424-4427; Angew. Chem. Int. Ed. 2000, 39, 4254-4258;
12. c) E. Nakamura, H. Isobe, N. Tomita, M. Sawamura, S. Jinno, H. Okayama, Angew. Chem. 2000, 112, 4424-4427; Angew. Chem. Int. Ed. 2000, 39, 4254-4258;
13. d) T. D. Ros, M. Bergamin, E. Vázquez, G. Spalluto, B. Baiti, S. Moro, A. Boutorine, M. Prato, Eur. J. Org. Chem. 2002, 405-413.
14. a) E. Yashima, S. Huang, Y. Okamoto, J. Chem. Soc. Chem. Commun. 1994, 1811-1812;
15. b) E. Yashima, S. Huang, T. Matsushima, Y. Okamoto, Macromolecules 1995, 28, 4184-4193;
16. c) E. Yashima, K. Maeda, O. Sato, J. Am. Chem. Soc. 2001, 123, 8159-8160;
17. d) K. Morino, K. Maeda, Y. Okamoto, E. Yashima, T. Sato, Chem. Eur. J. 2002, 8, 5112-5120;
18. e) E. Yashima, Anal. Sci. 2002, 18, 3-6.
19. For other recent examples, see: e) V. Percec, M. Obata, J. G. Rudick, B. B. De, M. Glodde, T. K. Bera, S. N. Magonov, V. S. K. Balagurusamy, P. A. Heiney, J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3509-3533;
20. f) A. P. H. J. Schenning, M. Fransen, E. W. Meijer, Macromol. Rapid Commun. 2002, 23, 265-270;
21. g) T. Aoki, T. Kaneko, N. Maruyama, A. Sumi, M. Takahashi, T. Sato, M. Teraguchi, J. Am. Chem. Soc. 2003, 125, 6346-6347;
22. h) B. S. Li, K. K. L. Cheuk, L. Ling, J. Chen, X. Xiao, C. Bai, B. Z. Tang, Macromolecules 2003, 36, 77-85.
23. For aliphatic polyacetylenes, see: i) R. Nomura, Y. Fukushima, H. Nakako, T. Masuda, J. Am. Chem. Soc. 2000, 122, 8830-8836;
24. j) R. Nomura, S. Nishiura, J. Tabei, F. Sanda, T. Masuda, Macromolecules 2003, 36, 5076-5080.
25. a) M. M. Green, N. C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science 1995, 268, 1860-1866;
26. b) M. M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3329-3345; Angew. Chem. Int. Ed. 1999, 38, 3138-3154;
27. b) M. M. Green, J.-W. Park, T. Sato, A. Teramoto, S. Lifson, R. L. B. Selinger, J. V. Selinger, Angew. Chem. 1999, 111, 3329-3345; Angew. Chem. Int. Ed. 1999, 38, 3138-3154;
28. c) T. Nakano, Y. Okamoto, Chem. Rev. 2001, 101, 4013-4038;
29. d) M. Fujiki, J. R. Koe, K. Terao, T. Sato, A. Teramoto, J. Watanabe, Polym. J. 2003, 35, 297-344;
30. e) E. Yashima, K. Maeda, T. Nishimura, Chem. Eur. J. 2004, 10, 42-51.
31. a) E. Yashima, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1995, 117, 11596-11597;
32. b) E. Yashima, T. Nimura, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1996, 118, 9800-9801;
33. c) E. Yashima, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1997, 119, 6345-6359;
34. d) E. Yashima, K. Maeda, Y. Okamoto, Nature 1999, 399, 449-451;
35. e) H. Onouchi, K. Maeda, E. Yashima, J. Am. Chem. Soc. 2001, 123, 7441-7442;
36. f) R. Nonokawa, E. Yashima, J. Am. Chem. Soc. 2003, 125, 1278-1283;
37. g) K. Maeda, K. Morino, Y. Okamoto, T. Sato, E. Yashima, J. Am. Chem. Soc. 2004, 126, 4329-4342;
38. h) T. Nishimura, S. Ohsawa, K. Maeda, E. Yashima, Chem. Commun. 2004, 646-647;
39. i) T. Nishimura, K. Tsuchiya, S. Ohsawa, K. Maeda, E. Yashima, Y. Nakamura, J. Nishimura, J. Am. Chem. Soc. 2004, 126, 11711-11717.
40. For other induced helical polymers, see: j) D. S. Schlitzer, B. M. Novak, J. Am. Chem. Soc. 1998, 120, 2196-2197;
41. k) E. Yashima, K. Maeda, T. Yamanaka, J. Am. Chem. Soc. 2000, 122, 7813-7814;
42. l) M. Ishikawa, K. Maeda, E. Yashima, J. Am. Chem. Soc. 2002, 124, 7448-7458;
43. m) M. Ishikawa, K. Maeda, Y. Mitsutsuji, E. Yashima, J. Am. Chem. Soc. 2004, 126, 732-733;
44. n) R. Sakai, T. Satoh, R. Kakuchi, H. Kaga, T. Kakuchi, Macromolecules 2004, 37, 3996-4003.
45. T. Nishimura, K. Takatani, S. Sakurai, K. Maeda, E. Yashima, Angew. Chem. 2002, 114, 3754-3756; Angew. Chem. Int. Ed. 2002, 41, 3602-3604.
46. T. Nishimura, K. Takatani, S. Sakurai, K. Maeda, E. Yashima, Angew. Chem. 2002, 114, 3754-3756; Angew. Chem. Int. Ed. 2002, 41, 3602-3604.
47. M. Maggini, G. Scorrano, M. Prato, J. Am. Chem. Soc. 1993, 115, 9798-9799.
48. K. Morino, K. Maeda, E. Yashima, Macromolecules 2003, 36, 1480-1486.
49. a) C. I. Simionescu, V. Percec, S. Dumitrescu, J. Polym. Sci. Polym. Chem. Ed. 1977, 15, 2497-2509;
50. b) C. I. Simionescu, V. Percec, Prog. Polym. Sci. 1982, 18, 133-214;
51. c) A. Furlani, C. Napoletano, M. V. Russo, W. Feast, J. Polym. Bull. 1986, 16, 311-317;
52. d) Y. Kishimoto, P. Eckerle, T. Miyatake, M. Kainosho, A. Ono, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1999, 121, 12035-12044.
53. a) H. Shirakawa, T. Ito, S. Ikeda, Polym. J. 1973, 4, 460-462;
54. b) M. Tabata, Y. Tanaka, Y. Sadahiro, T. Sone, K. Yokota, I. Miura, Macromolecules 1997, 30, 5200-5204.
55. H. Xu, B. Z. Tang, J. Macromol. Sci. Pure Appl. Chem. 1999, A36, 1197-1207.
56. 60 incorporated in the polymer main chain could not be determined.
57. For recent reviews of chiral fullerenes, see: a) C. Thilgen, F. Diederich in Topics in Current Chemistry, Vol. 199 (Ed.: A. Hirsch), Springer, Berlin, 1999, pp. 136-166;
58. b) F. Diederich, M. G. López, Chem. Soc. Rev. 1999, 28, 263-277;
59. c) A. Bianco, T. D. Ros, M. Prato, C. Toniolo, J. Pept. Sci. 2001, 7, 208-219;
60. d) Y. Nakamura, K. O-kawa, J. Nishimura, Bull. Chem. Soc. Jpn. 2003, 76, 865-882.
61. a) M. Maggini, G. Scorrano, A. Bianco, C. Toniolo, M. Prato, Tetrahedron Lett. 1995, 36, 2845-2846;
62. b) C. K. F. Shen, K. M. Chien, C. G. Juo, G. R. Her, T. Y. Luh, J. Org. Chem. 1996, 61, 9242-9244;
63. c) D. I. Schuster, J. Cao, N. Kaprinidis, Y. Wu, A. W. Jensen, Q. Lu, H. Wang, S. R. Wilson, J. Am. Chem. Soc. 1996, 118, 5639-5647;
64. d) A. Bianco, M. Maggini, G. Scorrano, C. Toniolo, G. Marconi, C. Villani, M. Prato, J. Am. Chem. Soc. 1996, 118, 4072-4080.
65. T. Ishi-i, K. Nakashima, S. Shinkai, A. Ikeda, J. Org. Chem. 1999, 64, 984-990.
66. a) J. Crassous, J. Rivera, N. S. Fender, L. Shu, L. Echegoyen, C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. 1999, 111, 1716-1721; Angew. Chem. Int. Ed. 1999, 38, 1613-1617;
67. a) J. Crassous, J. Rivera, N. S. Fender, L. Shu, L. Echegoyen, C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. 1999, 111, 1716-1721; Angew. Chem. Int. Ed. 1999, 38, 1613-1617;
68. b) F. Djojo, A. Hirsch, S. Grimme, Eur. J. Org. Chem. 1999, 3027-3039;
69. c) Y. Nakamura, K. O-kawa, M. Matsumoto, J. Nishimura, Tetrahedron 2000, 56, 5429-5434;
70. d) Y. Nakamura, K. O-kawa, T. Nishimura, E. Yashima, J. Nishimura, J. Org. Chem. 2003, 68, 3251-3257;
71. e) S. Sergeyev, F. Diederich, Angew. Chem. 2004, 116, 1770-1773; Angew. Chem. Int. Ed. 2004, 43, 1738-1740.
72. e) S. Sergeyev, F. Diederich, Angew. Chem. 2004, 116, 1770-1773; Angew. Chem. Int. Ed. 2004, 43, 1738-1740.
73. a) R. Nomura, J. Tabei, T. Masuda, J. Am. Chem. Soc. 2001, 123, 8430-8431;
74. b) R. Nomura, J. Tabei, S. Nishiura, T. Masuda, Macromolecules 2003, 36, 561-564;
75. c) K. K. L. Cheuk, J. W. Y. Lam, L. M. Lai, Y. Dong, B. Z. Tang, Macromolecules 2003, 36, 9752-9762.
76. a) M. M. Bouman, E. E. Havinga, R. A. J. Janssen, E. W. Meijer, Mol. Cryst. Liq. Cryst. 1994, 256, 439-448;
77. b) L. Pu, Acta Polym. 1997, 48, 116-141;
78. c) E. Yashima, H. Goto, Y. Okamoto, Macromolecules 1999, 32, 7942-7945;
79. d) Z.-B. Zhang, M. Fujiki, M. Motonaga, H. Nakashima, K. Torimitsu, H.-Z. Tang, Macromolecules 2002, 35, 941-944;
80. e) H. Goto, E. Yashima, J. Am. Chem. Soc. 2002, 124, 7943-7949;
81. f) H. Goto, Y. Okamoto, E. Yashima, Chem. Eur. J. 2002, 8, 4027-4036.
82. R. M. Silverstein, F. X. Webster, Spectrometric Identification of Organic Compounds, Wiley, New York, 1996, Chapter 3.
83. R. C. Paul, P. Singh, S. L. Chadha, Indian J. Chem. 1968, 6, 673-674.
84. a) L. Giovanelli, G. L. Lay, Appl. Surf Sci. 2000, 162-163, 513-518;
85. b) D. M. Guldi, M. Maggini, S. Mondini, F. Guérin, J. H. Fendler, Langmuir 2000, 16, 1311-1318;
86. c) S. Barazzouk, S. Hotchandani, P. V. Kamat, Adv. Mater. 2001, 13, 1614-1617;
87. d) J. Li, D. Qin, J. R. Baker Jr, D. A. Tomalia, Macromol. Symp. 2001, 166, 257-269;
88. e) G. Das, L. Ouali, M. Adrian, B. Baumeister, K. J. Wilkinson, S. Matile, Angew. Chem. 2001, 113, 4793-4797; Angew. Chem. Int. Ed. 2001, 40, 4657-4661.
89. e) G. Das, L. Ouali, M. Adrian, B. Baumeister, K. J. Wilkinson, S. Matile, Angew. Chem. 2001, 113, 4793-4797; Angew. Chem. Int. Ed. 2001, 40, 4657-4661.
90. S. Gao, L. Chi, S. Lenhert, B. Anczykowski, C. M. Niemeyer, M. Adler, H. Fuchs, ChemPhysChem 2001, 2, 384-388.
91. a) H. Tanaka, C. Hamai, T. Kanno, T. Kawai, Surf. Sci. 1999, 432, L611-L616;
92. b) P. Samori, V. Francke, K. Müllen, J. P. Rabe, Chem. Eur. J. 1999, 5, 2312-2317;
93. c) C. I. Zanetti, R. Khurana, J. R. Gillespie, J. S. Petrick, L. C. Trabachino, L. J. Minert, S. A. Carter, A. L. Fink, Proc. Natl. Acad. Sci. USA 1999, 96, 13175-13179;
94. d) Y. Maeda, T. Matsumoto, T. Kawai, Surf. Interface Anal. 1999, 27, 450-455;
95. e) T. Uchihashi, N. Choi, M. Tanigawa, M. Ashino, Y. Sugawara, H. Nishijima, S. Akita, Y. Nakayama, H. Tokumoto, K. Yokoyama, S. Morita, M. Ishikawa, Jpn. J. Appl. Phys. Part 2 2000, 39, L887-L889;
96. f) P. G. Khalatur, A. R. Khokhlov, S. A. Prokhorova, S. S. Sheiko, M. Möller, P. Reineker, D. G. Shirvanyanz, N. Starovoitova, Eur. Phys. J. 2000, E1, 99-103;
97. g) B. S. Li, K. K. L. Cheuk, F. Salhi, J. W. Y. Lam, J. A. K. Cha, X. Xiao, C. Bai, B. Z. Tang, Nano Lett. 2001, 1, 323-328;
98. h) K. Shinohara, S. Yasuda, G. Kato, M. Fujita, H. Shigekawa, J. Am. Chem. Soc. 2001, 123, 3619-3620;
99. i) S. S. Sheiko, M. Möller, Chem. Rev. 2001, 101, 4099-4123;
100. j) A. P. H. J. Schenning, A. F. M. Kilbinger, F. Biscarini, M. Cavallini, H. J. Cooper, P. J. Derrick, W. J. Feast, R. Lazzaroni, P. Leclère, L. A. McDonell, E. W. Meijer, S. C. J. Meskers, J. Am. Chem. Soc. 2002, 124, 1269-1275.
101. P. R. Serwinski, P. M. Lahti, Org. Lett. 2003, 5, 2099-2102.
102. a) S. L. Mayo, B. D. Olafson, W. A. Goddard III, J. Phys. Chem. 1990, 94, 8897-8909;
103. b) A. K. Rappé, W. A. Goddard III, J. Phys. Chem. 1991, 95, 3358-3363.