Synthesis, structure, and aromaticity of a hoop-shaped cyclic benzenoid [10]cyclophenacene

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 2834-2835

  Nakamura, Eiichi ^a   Tahara, Kazukuni ^a   Matsuo, Yutaka ^a   Sawamurat, Masaya ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; CYCLOPHENACENE DERIVATIVE; FULLERENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CRYSTAL STRUCTURE; ELECTRON SPIN RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037433499     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029915z     Document Type: Article

References (37)

1. Schröder, A.; Mekelburger, H.-B.; Vögtle, F. Top. Curr. Chem. 1994, 172, 179.
2. Cory, R. M.; McPhail, C. L. Adv. Theor. Interesting Mol. 1998, 4, 53.
3. (a) Heilbronner, E. Helv. Chim. Acta 1954, 37, 921.
4. (b) Vögtle, F. Top. Curr. Chem. 1983, 115, 157.
5. (a) Choi, H. S.; Kim, K. S. Angew. Chem., Int. Ed. 1999, 38, 2256.
6. (b) Houk, K. N.; Lee, P. S.; Nendel, M. J. Org. Chem. 2001, 66, 5517.
7. (c) Türker, L. J. Mol. Struct. (THEOCHEM) 1999, 491, 275.
8. (d) Aihara, J. J. Chem. Soc., Perkin Trans. 2 1994, 971.
9. (e) Kanamitsu, K.; Saito, S. J. Phys. Soc. Jpn. 2002, 71, 483.
10. Saito, R.; Dresselhaus, G.; Dresselhaus, M. S. Physical Properties of Carbon Nanotubes; Imperial College Press: London, 1998.
11. (a) Wildöer, J. W. G.; Venema, L. C.; Rinzler, A. G.; Smalley, R. E.; Dekker, C. Nature 1998, 391, 59.
12. (b) Odom, T. W.; Huang, J.-L.; Kim, P.; Lieber, C. M. Nature 1998, 391, 62.
13. Mallory, F. B.; Butler, K. E.; Evans, A. C.; Brondyke, E. J.; Mallory, C. W.; Yang, C.; Ellenstein, A. J. Am. Chem. Soc. 1997, 119, 2119.
14. For the [10]cyclophenacene, there exist 121 other canonical resonance structures in addition to (a)-(b) shown in Figure 1a, and the calculation of the Pauling bond order assuming equal contribution of all 125 structures matches very well with the experimental X-ray structure. We thank a referee for pointing out this issue for us.
15. (a) Godt, A.; Enkelmann, V.; Schlüter, A. D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1680.
16. (b) Ashton, P. R.; Brown, G. R.; Isaacs, N. S.; Giuffrid, D.; Kohnke, F. H.; Mathias, J. P.; Slawin, A. M. Z.; Smith, D. R.; Stoddart, J. F.; Williams, D. J. J. Am. Chem. Soc. 1993. 115, 5422.
17. (c) Kuwatani, Y.; Yoshida, T.; Kusaka, A.; Iyoda, M. Tetrahedron Lett. 2000, 41, 359.
18. (d) St. Martin, H. M.; Scott, L. T. The Tenth International Symposium on Novel Aromatic Compounds; Abstract No. P77, August 2001, San Diego, California.
19. (a) Sawamura, M.; Iikura, H.; Nakamura, E. J. Am. Chem. Soc. 1996, 118, 12850.
20. (b) Nakamura, E.; Sawamura, M. Pure Appl. Chem. 2001, 73, 355.
21. Sawamura, M.; Toganoh, M.; Kuninobu, Y.; Kato, S.; Nakamura, E. Chem. Lett. 2000, 270.
22. An inseparable mixture of other multiadducts was obtained in about 50% yield.
23. (a) Rochefort, A.; Salahub, D. R.; Avouris, P. J. Phys. Chem. B 1999, 103, 641.
24. (b) Cioslowski, J.; Rao, N.; Moncrieff, D. J. Am. Chem. Soc. 2002, 124, 8489.
25. (c) Tanaka, K.; Ago, H.; Yamabe, T.; Okahara, K.; Okada, M. Int. J. Quantum Chem. 1997, 63, 637.
26. (d) Liu, L.; Jayanthi, C. S.; Guo, H.; Wu, S. Y. Phys. Rev. B 2001, 64, 033414.
27. Liu, S.; Lu, Y.; Kappes, M. M.; Ibers, J. A. Science 1991, 254, 408.
28. Kveseth, K.; Seip, R.; Kohl, D. A. Acta Chem. Scand. 1980, A34, 31.
29. The important difference between [60]fullerene and the present 40 π electron system is that the latter does not involve a pentagon within the conjugate system and hence is a rolled graphite.
30. (a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. van E. J. Am. Chem. Soc. 1996, 118, 6317,
31. (b) Bühl, M.; Hirsch, A. Chem. Rev. 2001, 101, 1153.
32. Saunders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Mroczkowski, S.; Freedberg, D. I.; Anet, F. A. L. Nature 1994, 367, 256.
33. (a) O'Connell, M. J.; Bachilo, S. M.; Huffman, C. B.; Moore, V. C.; Strano, M. S.; Haroz, E. H.; Rialon, K. L.; Boul, P. J.; Noon, W. H.; Kittrell, C.; Ma, J.; Hauge, R. H.; Weisman, R. B.; Smalley, R. E. Science 2002, 297, 593.
34. (b) Nagasawa, N.; Sugiyama, H.; Naka, N.; Kudryashov, I.; Watanabe, M.; Hayashi, T.; Bozovic, I.; Bozovic, N.; Li, G.; Li, Z.; Tang, Z. K. J. Luminescence 2002, 97, 161.
35. Sawamura, M.; Kawai, K.; Matsuo, Y.; Kanie, K.; Kato, T.; Nakamura, E. Nature 2002, 419, 702.
36. (a) Sawamura, M.; Kuninobu, Y.; Nakamura, E. J. Am. Chem. Soc. 2000, 122, 12407.
37. (b) Sawamura, M.; Kuninobu, Y.; Toganoh, M.; Matsuo, Y.; Yamanaka, M.; Nakamura, E. J. Am. Chem. Soc. 2002, 124, 9354.