Unambiguous identification of Möbius aromaticity for meso-aryl-substituted [28]hexaphyrins(1.1.1.1.1.1)

Journal of the American Chemical Society

Volumn 130, Issue 41, 2008, Pages 13568-13579

  Sankar, Jeyaraman ^a   Mori, Shigeki ^a   Saito, Shohei ^a   Rath, Harapriya ^a   Suzuki, Masaaki ^a   Inokuma, Yasuhide ^a   Shinokubo, Hiroshi ^a   Kil, Suk Kim ^b   Zin, Seok Yoon ^b   Shin, Jae Yoon ^b   Jong, Min Lim ^b   Matsuzaki, Yoichi ^d   Matsushita, Osamu ^c   Muranaka, Atsuya ^c   Kobayashi, Nagao ^c   Kim, Dongho ^b   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Yonsei University   (South Korea)

^c TOHOKU UNIVERSITY   (Japan)

^d NIPPON STEEL CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATICITY; HEXAPHYRINS;

MOLYBDENUM;

HEXAPHYRIN DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; CONJUGATION; CRYSTALLIZATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

EID: 53849084491     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja801983d     Document Type: Article

References (51)

1. (a) Hückel, E. Z. Phys. 1931, 70, 204-286.
2. (b) Hückel, E. Z. Phys. 1932, 76, 628-648.
3. (a) Rzepa, H. S. Chem. Rev. 2005, 105, 3697-3715.
4. (b) Herges, R. Chem. Rev. 2006, 106, 4820-4842.
5. Heilbronner, E. Tetrahedron Lett. 1964, 5, 1923-1926.
6. Zimmerman, H. E. J. Am. Chem. Soc. 1966, 88, 1564-1567.
7. Mauksch, M.; Gogonea, V.; Jiao, H.; Schleyer, P. v. R. Angew. Chem., Int. Ed. 1998, 37, 2395-2398.
8. (a) The Walsh model for cyclopropane was first proposed in: Walsh, A. D. Nature 1947, 159, 165.
9. (b) It was organized in: Walsh, A. D. Trans. Faraday Soc. 1949, 45, 179-190.
10. (c) In this context, Zimmerman indicated that the p orbitals of the model could be treated as a Möbius circle, as well as those of barrelene and allene. See: Zimmerman, H. E. Acc. Chem. Res. 1971, 4, 272-280, and references therein.
11. (a) Ajami, D.; Oeckler, O.; Simon, A.; Herges, R. Nature 2003, 426, 819-821.
12. (b) Ajami, D.; Hess, K.; Köhler, F.; Näther, C.; Oeckler, O.; Simon, A.; Yamamoto, C.; Okamoto, Y.; Herges, R. Chem. - Eur. J. 2006, 12, 5434-5455.
13. Castro, C.; Chen, Z.; Wannere, C. S.; Jiao, H.; Karney, W. L.; Mauksch, M.; Puchta, R.; Hommes, N. J. R. v. E.; Schleyer, P. v. R. J. Am. Chem. Soc. 2005, 127, 2425-2432.
14. Stepień, M.; Latos-Grażyński, L.; Sprutta, N.; Chwalisz, P.; Szterenberg, L. Angew. Chem., Int. Ed. 2007, 46, 7869-7873.
15. (a) Jasat, A.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
16. (b) Lash, T. D. Angew. Chem., Int. Ed. 2000, 39, 1763-1767.
17. (c) Furuta, H.; Maeda, H.; Osuka, A. Chem. Commun. 2002, 1795-1804.
18. (d) Sessler, J. L.; Seidel, D. Angew. Chem., Int. Ed. 2003, 42, 5134-5157.
19. (e) Chandrashekar, T. K.; Venkatraman, S. Acc. Chem. Res. 2003, 36, 676-691.
20. (a) Shin, I.-Y.; Furuta, H.; Yoza, K.; Igarashi, S.; Osuka, A. J. Am. Chem. Soc. 2001, 123, 7190-7191.
21. (b) Taniguchi, R.; Shimizu, S.; Suzuki, M.; Shin, J.-Y.; Furuta, H.; Osuka, A. Tetrahedron Lett. 2003, 44, 2502-2507.
22. (c) Suzuki, M.; Osuka, A. Org. Lett. 2003, 5, 3943-3946.
23. (a) Tanaka, Y.; Saito, S.; Mori, S.; Aratani, N.; Shinokubo, H.; Shibata, N.; Higuchi, Y.; Yoon, Z. S.; Kim, K. S.; Noh, S. B.; Park, J. K.; Kim, D.; Osuka, A. Angew. Chem., Int. Ed. 2008, 47, 681-684.
24. (b) Jux, N. Angew. Chem., Int. Ed. 2008, 47, 2543-2546.
25. Park, J. K.; Yoon, Z. S.; Yoon, M.-C.; Kim, K. S.; Mori, S.; Shin, J.-Y.; Osuka, A.; Kim, D. J. Am. Chem. Soc. 2008, 130, 1824-1825.
26. Neves, M. G. P. M. S.; Martins, R. M.; Tomé, A. C.; Silvestre, A. J. D.; Silva, A. M. S.; Félix, V.; Drew, M. G. B.; Cavaleiro, J. A. S. Chem. Commun. 1999, 385-386.
27. (a) Mori, S.; Osuka, A. J. Am. Chem. Soc. 2005, 127, 8030-8031.
28. (b) Mori, S.; Kim, K. S.; Yoon, Z. S.; Noh, S. B.; Kim, D.; Osuka, A. J. Am. Chem. Soc. 2007, 129, 11344-11345.
29. (a) Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; Hommes, N. J. R. v. E. J. Am. Chem. Soc. 1996, 118, 6317-6318.
30. (b) Schleyer, P. v. R.; Jiao, H.; Hommes, N. J. R. v. E.; Malkin, V. G.; Malkina, O. L. J. Am. Chem. Soc. 1997, 119, 12669-12670.
31. (c) Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R Chem. Rev. 2005, 105, 3842-3888.
32. Suzuki, M.; Shimizu, S.; Shin, J.-Y.; Osuka, A. Tetrahedron Lett. 2003, 44, 4597-4601.
33. Krygowski, T. M. J. Chem. Inf. Comput. Sci. 1993, 33, 70-78, HOMA values are a quantitative measure of bond-length equalization for π-electron systems. HOMA = 0 for the Kekulé structure of an aromatic system, and HOMA = 1 for the system with all bonds equal to the optimal value, such as in benzene.
34. (a) Mason, W. R. A Practical Guide to Magnetic Circular Dichroism Spectroscopy; John Wiley & Sons Inc.: Hoboken, NJ, 2007.
35. (b) Rodger, A.; Norden, B. Circular Dichroism and Linear Dichroism; Oxford University Press: Oxford, U.K., 1997.
36. (a) Michl, J. J. Am. Chem. Soc. 1978, 100, 6801-6811.
37. (b) Michl, J. J. Am. Chem. Soc. 1978, 100, 6812-6818.
38. (c) Mack, J.; Asano, Y.; Kobayashi, N.; Stillman, M. J. J. Am. Chem. Soc. 2005, 127, 17697-17711.
39. (a) Keegan, J. D.; Stolzenberg, A. M.; Lu, Y.-C.; Linder, R. E.; Barth, G.; Moscowitz, A.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1982, 104, 4305-4317.
40. (b) Keegan, J. D.; Stolzenberg, A. M.; Lu, Y.-C.; Linder, R. E.; Barth, G.; Moscowitz, A.; Bunnenberg, E.; Djerassi, C. J. Am. Chem. Soc. 1982, 104, 4317-4329.
41. Mack, J.; Stillman, M. J. Coord. Chem. Rev. 2001, 219-221, 993-1032.
42. Waluk, J.; Müller, M.; Swiderek, P.; Köcher, M.; Vogel, E.; Hohlneicher, G.; Michl, J. J. Am. Chem. Soc. 1991, 113, 5511-5527.
43. Waluk, J.; Hemmi, G.; Sessler, J. L.; Michl, J. J. Org. Chem. 1991, 56, 2735-2742.
44. Gorski, A.; Lament, B.; Davis, J. M.; Sessler, J. L; Waluk, J. J. Phys. Chem. A 2001, 105, 4992-4999.
45. Lament, B.; Rachlewicz, K.; Latos-Grażyński, L.; Waluk, J. ChemPhysChem 2002, 3, 849-855.
46. Gorski, A.; Köhler, T.; Seidel, D.; Lee, J. T.; Orzanowska, G.; Sessler, J. L.; Waluk, J. Chem. - Eur. J. 2005, 11, 4179-4184.
47. Gouterman, M. In The Porphyrins, Vol. III: Physical Chemistry, Part A; Dolphin, D., Ed.;Academic Press: New York, 1978.
48. Platt, J. R. J. Chem. Phys. 1949, 17, 484-495.
49. (a) Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
50. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
51. (c) Theoretical calculations were performed with the Gaussian 03 package: Frisch, M. J.; et al. Gaussian 03, revision B.05; Gaussian, Inc.: Wallingford, CT, 2004.