Bowl-shaped fragments of C70 or higher fullerenes: Synthesis, structural analysis, and inversion dynamics

Angewandte Chemie - International Edition

Volumn 52, Issue 4, 2013, Pages 1289-1293

  Wu, Tsun Cheng ^a   Chen, Min Kuan ^a   Lee, Yen Wei ^b   Kuo, Ming Yu ^b   Wu, Yao Ting ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^b NATIONAL CHI NAN UNIVERSITY   (Taiwan)

Author keywords

alkynes; buckybowl; cycloaddition; fullerenes; inversion dynamics

Indexed keywords

ALKYNES; BUCKYBOWL; CURVED STRUCTURE; HIGHER FULLERENES; INVERSION BARRIERS; S-SHAPED; SUPER BOWL; TRANSITION STRUCTURES;

ACETYLENE; CYCLOADDITION; DYNAMICS; NAPHTHALENE; X RAY CRYSTALLOGRAPHY;

FULLERENES;

EID: 84872385745     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201208200     Document Type: Article

References (60)

1. A. L. Balch, M. M. Olmstead, Chem. Rev. 1998, 98, 2123
2. Fullerenes: Principles and Applications (Eds.:, F. Langa, J.-F. Nierengarten,), RSC, Cambridge, 2007
3. C. Thilgen, F. Diederich, Chem. Rev. 2006, 106, 5049
4. A. Hirsch, M. Brettreich, Fullerenes: Chemistry and Reactions, Wiley-VCH, Weinheim, 2005
5. "Fullerenes and Related Structures": Topics in Current Chemistry, Vol. 199 (Ed.:, A. Hirsch,), Springer, Berlin, 1999.
6. H. B. Bürgi, E. Blanc, D. Schwarzenbach, S. Liu, Y. Lu, M. M. Kappes, J. A. Ibers, Angew. Chem. 1992, 104, 667
7. Angew. Chem. Int. Ed. Engl. 1992, 31, 640.
8. 6]
9. 70×Ni] complex
10. 70×azatriquinacene]
11. D. Pham, J. Ceron-Bertran, M. M. Olmstead, M. Mascal, A. L. Balch, Cryst. Growth Des. 2007, 7, 75; electron diffraction
12. K. Hedberg, L. Hedberg, M. Bühl, D. S. Bethune, C. A. Brown, R. D. Johnson, J. Am. Chem. Soc. 1997, 119, 5314
13. D. R. McKenzie, C. A. Davis, D. J. H. Cockayne, D. A. Muller, A. M. Vassallo, Nature 1992, 355, 622; neutron diffraction
14. A. V. Nikolaev, T. J. S. Dennis, K. Prassides, A. K. Soper, Chem. Phys. Lett. 1994, 223, 143.
15. Fragments of Fullerenes and Carbon Nanotubes: Designed Synthesis, Unusual Reactions, and Coordination Chemistry (Eds.:, M. A. Petrukhina, L. T. Scott,), Wiley, Hoboken, 2012
16. A. Sygula, Eur. J. Org. Chem. 2011, 1611
17. S. Higashibayashi, H. Sakurai, Chem. Lett. 2011, 40, 122
18. T. Amaya, T. Hirao, Chem. Commun. 2011, 47, 10524
19. V. M. Tsefrikas, L. T. Scott, Chem. Rev. 2006, 106, 4868
20. Y.-T. Wu, J. S. Siegel, Chem. Rev. 2006, 106, 4843
21. A. Sygula, P. W. Rabideau, in Carbon-Rich Compounds: From Molecules to Materials (Eds.:, M. M. Haley, R. R. Tykwinski,), Willey-VCH, Weinheim, 2006, pp. 529.
22. K. K. Baldridge, J. S. Siegel, Theor. Chem. Acc. 1997, 97, 67.
23. F. C. Krebs, P. S. Larsen, J. Larsen, C. S. Jacobsen, C. Boutton, N. Thorup, J. Am. Chem. Soc. 1997, 119, 1208
24. G. K. H. Madsen, F. C. Krebs, B. Lebech, F. K. Larsen, Chem. Eur. J. 2000, 6, 1797; for a review, see
25. D. Y. Curtin, I. C. Paul, Chem. Rev. 1981, 81, 525.
26. H. A. Wegner, H. Reisch, K. Rauch, A. Demeter, K. A. Zachariasse, A. de Meijere, L. T. Scott, J. Org. Chem. 2006, 71, 9080.
27. P. W. Fowler, D. E. Manolopoulos, An Atlas of Fullerenes, Dover Publications, Mineola, 2006
28. C. Thilgen, A. Herrmann, F. Diederich, Angew. Chem. 1997, 109, 2362
29. Angew. Chem. Int. Ed. Engl. 1997, 36, 2268
30. R. Taylor, J. Chem. Soc. Perkin Trans. 2 1993, 813.
31. 2v)×Cu]:, L. Epple, K. Y. Amsharov, M. Jansen, Fullerenes Nanotubes Carbon Nanostruct. 2009, 17, 67.
32. s)×Ag] complex:, L. Epple, K. Amsharov, K. Simeonov, I. Dix, M. Jansen, Chem. Commun. 2008, 5610.
33. T.-C. Wu, H.-J. Hsin, M.-Y. Kuo, C.-H. Li, Y.-T. Wu, J. Am. Chem. Soc. 2011, 133, 16319.
34. E. A. Jackson, B. D. Steinberg, M. Bancu, A. Wakamiya, L. T. Scott, J. Am. Chem. Soc. 2007, 129, 484
35. B. D. Steinberg, E. A. Jackson, A. S. Filatov, A. Wakamiya, M. A. Petrukhina, L. T. Scott, J. Am. Chem. Soc. 2009, 131, 10537
36. H.-I. Chang, H.-T. Huang, C.-H. Huang, M.-Y. Kuo, Y.-T. Wu, Chem. Commun. 2010, 46, 7241
37. A. C. Whalley, K. N. Plunkett, A. A. Gorodetsky, C. L. Schenck, C.-Y. Chiu, M. L. Steigerwald, C. Nuckolls, Chem. Sci. 2011, 2, 132; for other nonpyrolysis coupling techniques, see
38. Y.-T. Wu, T. Hayama, K. K. Baldridge, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870
39. K. T. Rim, M. Siaj, S. Xiao, M. Myers, V. D. Carpentier, L. Liu, C. Su, M. L. Steigerwald, M. S. Hybertsen, P. H. McBreen, G. W. Flynn, C. Nuckolls, Angew. Chem. 2007, 119, 8037
40. Angew. Chem. Int. Ed. 2007, 46, 7891
41. O. Allemann, S. Duttwyler, P. Romanato, K. K. Baldridge, J. S. Siegel, Science 2011, 332, 574
42. K. Y. Amsharov, M. A. Kabdulov, M. Jansen, Angew. Chem. 2012, 124, 4672
43. Angew. Chem. Int. Ed. 2012, 51, 4594.
44. CCDC 901335 (9 aa) and 901336 (9 ba) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
45. A. Sygula, H. E. Folsom, R. Sygula, A. H. Abdourazak, Z. Marcinow, F. R. Fronczek, P. W. Rabideau, J. Chem. Soc. Chem. Commun. 1994, 2571; for the structure/energy correlation of corannulene-based buckybowls, see
46. T. J. Seiders, K. K. Baldridge, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc. 2001, 123, 517.
47. H. Sakurai, T. Daiko, H. Sakane, T. Amaya, T. Hirao, J. Am. Chem. Soc. 2005, 127, 11580.
48. T. M. Krygowski, M. Cyranski, A. Ciesielski, B. Swirska, P. Leszczynski, J. Chem. Inf. Comput. Sci. 1996, 36, 1135.
49. R. C. Haddon, L. T. Scott, Pure Appl. Chem. 1986, 58, 137
50. R. C. Haddon, Acc. Chem. Res. 1988, 21, 243
51. R. C. Haddon, Science 1993, 261, 1545.
52. L. Pauling, The Nature of the Chemical Bond, 3 rd ed., Cornell University Press, Ithaca, 1960. According to the Zefirov's definition, the sum of van der Waals radii of two carbon atoms is 3.42 Å, see
53. Y. V. Zefirov, Crystallogr. Rep. 1997, 42, 111.
54. T. J. Seiders, K. K. Baldridge, E. L. Elliott, G. H. Grube, J. S. Siegel, J. Am. Chem. Soc. 1999, 121, 7439
55. A. Sygula, A. H. Abdourazak, P. W. Rabideau, J. Am. Chem. Soc. 1996, 118, 339
56. L. T. Scott, M. M. Hashemi, M. S. Bratcher, J. Am. Chem. Soc. 1992, 114, 1920.
57. T. Amaya, K. Mori, H. L. Wu, S. Ishida, J. Nakamura, K. Murata, T. Hirao, Chem. Commun. 2007, 1902
58. H. Sakurai, T. Daiko, T. Hirao, Science 2003, 301, 1878.
59. S. Higashibayashi, H, Sakurai, J. Am. Chem. Soc. 2008, 130, 8592
60. Q. Tan, S. Higashibayashi, S. Karanjit, H. Sakurai, Nat. Commun. 2012, 3, 891.