A helical array of pendant fullerenes on an optically active polyphenylacetylene

Angewandte Chemie - International Edition

Volumn 41, Issue 19, 2002, Pages 3602-3604

  Nishimura, Tatsuya ^a   Takatani, Kohei ^a   Sakurai, Shin Ichiro ^a   Maeda, Katsuhiro ^a   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Chirality; Circular dichroism; Fullerenes; Helical structures; Polymerization

Indexed keywords

CHROMOPHORES; COPOLYMERIZATION; POLYPROPYLENES;

HELICAL ARRAYS;

FULLERENES;

ACETYLENE DERIVATIVE; BENZENE DERIVATIVE; COPOLYMER; FULLERENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; OPTICAL ROTATION; POLYMERIZATION;

EID: 0037020422     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021004)41:19<3602::AID-ANIE3602>3.0.CO;2-4     Document Type: Article

References (36)

1. a) M. Prato, J. Mater. Chem. 1997, 7, 1097-1109;
2. b) Y. Chen, Z. Huang, R. F. Cai, B. C. Yu, Eur. Polym. J. 1998, 34, 137-151;
3. c) M. Prato, M. Maggini, Acc. Chem. Res. 1998, 31, 519-526.
4. A. W. Jensen, S. R. Wilson, D. I. Schuster, Bioorg. Med. Chem. 1996, 4, 767-779.
5. a) E. Yashima, S. Huang, Y. Okamoto, J. Chem. Soc. Chem. Commun. 1994, 1811-1812;
6. b) E. Yashima, S. Huang, T. Matsushima, Y. Okamoto, Macromolecules 1995, 28, 4184-4193;
7. c) E. Yashima, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1997, 119, 6345-6359;
8. e) E. Yashima, K. Maeda, Y. Okamoto, Nature 1999, 399, 449-451;
9. f) E. Yashima, K. Maeda, O. Sato, J. Am. Chem. Soc. 2001, 123, 8159-8160.
10. A. M. Cassell, W. A. Scrivens, J. M. Tour, Angew. Chem. 1998, 110, 1670-1672; Angew. Chem. Int. Ed. 1998, 37, 1528-1531.
11. A. M. Cassell, W. A. Scrivens, J. M. Tour, Angew. Chem. 1998, 110, 1670-1672; Angew. Chem. Int. Ed. 1998, 37, 1528-1531.
12. M. Maggini, G. Scorrano, M. Prato, J. Am. Chem. Soc. 1993, 115, 9798-9799.
13. K. Morino, K. Maeda, Y. Okamoto, E. Yashima, T. Sato, Chem. Eur. J., in press.
14. 60 groups derived from 1 in the copolymers.
15. For recent reviews of chiral fullerenes, see: a) C. Thilgen, F. Diederich, Top. Curr. Chem. 1999, 199, 136-166; b) F. Diederich, M. G. López, Chem. Soc. Rev. 1999, 28, 263-277.
16. For recent reviews of chiral fullerenes, see: a) C. Thilgen, F. Diederich, Top. Curr. Chem. 1999, 199, 136-166; b) F. Diederich, M. G. López, Chem. Soc. Rev. 1999, 28, 263-277.
17. a) M. Maggini, G. Scorrano, A. Bianco, C. Toniolo, M. Prato, Tetrahedron Lett. 1995, 36, 2845-2846;
18. b) C. K. F. Shen, K. M. Chien, C. G. Juo, G. R. Her, T Y. Luh, J. Org. Chem. 1996, 61, 9242-9244;
19. 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;
20. d) A. Bianco, M. Maggini, G. Scorrano, C. Toniolo, G. Marconi, C. Villani, M. Prato, J. Am. Chem. Soc, 1996, 118, 4072-4080.
21. T. Ishi-i, K. Nakashima, S. Shinkai, A. Ikeda, J. Org. Chem. 1999, 64, 984-990.
22. a) J. Crassous, J. Rivera, N. S. Fender, L. Shu, L. Echegoyen, C. Thilgen, A. Herrmann, E Diederich, Angew. Chem. 1999, 111, 1716-1721; Angew. Chem. Int. Ed. 1999, 38, 1613-1617;
23. a) J. Crassous, J. Rivera, N. S. Fender, L. Shu, L. Echegoyen, C. Thilgen, A. Herrmann, E Diederich, Angew. Chem. 1999, 111, 1716-1721; Angew. Chem. Int. Ed. 1999, 38, 1613-1617;
24. b) F. Djojo, A. Hirsch, S. Grimme, Eur J. Org. Chem. 1999, 3027-3039;
25. c) Y. Nakamura, K. O-kawa, M. Matsumoto, J. Nishimura, Tetrahedron 2000, 56, 5429-5434.
26. a) L. Giovanelli, G. L. Lay, Appl. Surf. Sci. 2000, 162-163, 513-518;
27. b) D. M. Guldi, M. Maggini, S. Mondini. F. Guérin, J. H. Fendler. Langmuir 2000, 16, 1311-1318;
28. c) S. Barazzouk, S. Hotchandani, P. V. Kamat, Adv. Mater. 2001, 13, 1614-1617;
29. d) J. Li, D. Qin, J. R. Baker, Jr, D. A. Tomalia, Macromol. Symp. 2001, 166, 257-269;
30. 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.
31. 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.
32. 0.9) on HOPG was shorter than the molecular diameter of a model helical copolymer (Figure 2). A tip-induced deformation of the samples may be taken into consideration for the reduced height of the copolymer. S. Gao, L. Chi, S. Lenhert, B. Anczykowski, C. M. Niemeyer, M. Adler, H. Fuchs, ChemPhysChem 2001, 384-388.
33. a) P. Samori, V. Francke, K. Müllen, J. P. Rabe, Chem. Eur J. 1999, 5, 2312-2317;
34. b) P. G. Khalatur, A. R. Khokhlov, S. A. Prokhorova, S. S. Sheiko, M. Müller, P. Reineker, D. G. Shirvanyanz, N. Starovoitova, Eur. Phys. J. E1 2000, 1, 99-103;
35. c) 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.
36. K. Shinohara, S. Satoshi, G. Kato, M. Fujita, H. Shigekawa, J. Am. Chem. Soc. 2001, 123, 3619-3620.