Synthesis and explosive decomposition of organometallic dehydro[18] annulenes: An access to carbon nanostructures

Journal of the American Chemical Society

Volumn 124, Issue 46, 2002, Pages 13814-13818

  Laskoski, Matthew ^a   Steffen, Winfried ^a   Morton, Jason G M ^a   Smith, Mark D ^a   Bunz, Uwe H F ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EXPLOSIVE DECOMPOSITION;

DECOMPOSITION; DERIVATIVES; HIGH RESOLUTION ELECTRON MICROSCOPY; NANOSTRUCTURED MATERIALS; SOOT; SYNTHESIS (CHEMICAL); TRANSMISSION ELECTRON MICROSCOPY;

ORGANOMETALLICS;

1,2 DIETHYNYL 3,4 BIS(TRIMETHYLSILYL)CYCLOBUTADIENE(CYCLOPENTADIENYL)COBALT; 1,2 DIETHYNYLFERROCENE; CARBON; COPPER COMPLEX; DEHYDRO[18]ANNULENE; FERROCENE; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DECOMPOSITION; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE; TRANSMISSION ELECTRON MICROSCOPY;

EID: 0037146009     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026809o     Document Type: Article

References (54)

1. (a) Dresselhaus, M. S.; Dresselhaus, G.; Eklund, P. C. Science of Fullerenes and Carbon Nanotubes; Academic Press: San Diego, CA, 1996.
2. (b) For carbon nanotubes formation see: Terrones, M.; Hsu, W. K.; Kroto, H. W.; Walton, D. R. M. Top. Curr. Chem. 1999, 199, 189-234.
3. (c) Sinnott, S. B.; Andrews, R. Crit. Rev. Solid State Mater. Sci. 2001, 26, 145-249.
4. (d) Iijima, S. Nature 1991, 354, 56-58. Ajayan, P. M. Chem. Rev. 1999, 99, 1787-1799.
5. (d) Iijima, S. Nature 1991, 354, 56-58. Ajayan, P. M. Chem. Rev. 1999, 99, 1787-1799.
6. (e) Ugarte, D. Carbon 1995, 33, 989-993.
7. (f) Ugarte, D. Carbon 1994, 32, 1245-1248.
8. (a) Che, G. L.; Lakshmi, B. B.; Martin, C. R.; Fisher, E. R. Langmuir 1999, 15, 750-758.
9. (b) Dahn, J. R.; Zheng, T.; Liu, Y. H.; Xue, J. S. Science 1995, 270, 590-593.
10. Rao, A. M.; Richter, E.; Bandow, S.; Chase, B.; Eklund, P. C.; Williams, K. A.; Fang, S.; Subbaswamy, K. R.; Menon, M.; Thess, A.; Smalley, R. E.; Dresselhaus, G.; Dresselhaus, M. S. Science 1997, 275, 187-191.
11. Dillon, A. C.; Jones, K. M.; Bekkedahl, T. A.; Kiang, C. H.; Bethune, D. S.; Heben, M. J. Nature 1997, 386, 377-379.
12. Tans, S. J.; Devoret, M. H.; Dai, H. J.; Thess, A.; Smalley, R. E.; Geerligs, L. J.; Dekker, C. Nature 1997, 386, 474-477.
13. Rao, C. N. R.; Satishkumar, B. C.; Govindaraj, A.; Nath, M. Chem. Phys. Chem. 2001, 2, 78-105.
14. (a) Rubin, Y.; Parker, T. C.; Pastor, S. J.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem., Int. Ed. 1998, 37, 1226-1229.
15. (b) Tobe, Y.; Nakagawa, N.; Naemura, K.; Wakabayashi, T.; Shida, T.; Achiba, Y. J. Am. Chem. Soc. 1998, 120, 4544-4545.
16. 60 see: Scott, L. T.; Boorum, M. M.; McMahon, B. J.; Hagen, S.; Mack, J.; Blank, J.; Wegner, H.; de Meijere, A. Science 2002, 295, 1500-1503.
17. (a) De Meijere. A.; Kozhushkov, S.; Haumann, T.; Boese, R.; Puls, C.; Cooney, M. J.; Scott, L. T. Chem. Eur. J. 1995, 1, 124-131.
18. (b) Zhou, Q.; Carroll, P. J.; Swager, T. M. J. Org. Chem. 1994, 59, 1294-1301.
19. (c) Bunz, U. H. F.; Enkelmann, V. Chem. Eur. J. 1999, 5, 263-266.
20. (a) Boese, R.; Matzger, A. J.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1997, 119, 2052-2053.
21. (b) Dosa, P. I.; Erben, C.; Iyer, V. S.; Vollhardt, K. P. C.; Wasser, I. M. J. Am. Chem. Soc. 1999, 121, 10430-10431.
22. (c) Faust, R. Angew. Chem., Int. Ed. 1998, 37, 2825-2828.
23. (a) Bunz, U. H. F. Top. Curr. Chem. 1999, 201, 131-161.
24. (b) Bunz, U. H. F.; Rubin, Y.; Tobe, Y. Chem. Soc. Rev. 1999, 28, 107-119.
25. (a) Laskoski, M.; Steffen, W.; Smith, M. D.; Bunz, U. H. F. Chem. Commun. 2001, 691-692.
26. (b) Laskoski, M.; Roidl, G.; Smith, M. D.; Bunz, U. H. F. Angew. Chem., Int. Ed. 2001, 49, 1460-1463.
27. (c) Laskoski, M.; Smith, M. D.; Morton, J. G. M.; Bunz, U. H. F. J. Org. Chem. 2001, 66, 5174-5181.
28. (a) Baldwin, K. P.; Matzger, A. J.; Scheiman, D. A.; Tessier, C. A.; Vollhardt, K. P. C.; Youngs, W. J. Synlett 1995, 1215-1218.
29. (b) Enkelmann, V. Adv. Polym. Sci. 1984, 63, 91-136. Wegner, G. Z Naturforsch. 1969, 24b, 824-832.
30. (b) Enkelmann, V. Adv. Polym. Sci. 1984, 63, 91-136. Wegner, G. Z Naturforsch. 1969, 24b, 824-832.
31. (c) Hädicke, E.; Mez, E. C.; Krauch, C. H.; Wegner, G.; Kaiser, J. Angew. Chem., Int. Ed. Engl. 1971, 10, 266-267.
32. (a) Fritch. J. R.; Vollhardt, K. P. C. Organometallics 1982, 1, 590-602.
33. (b) Roidl, G.; Enkelmann, V.; Adams, R. D.; Bunz, U. H. F. J. Organomet. Chem. 1999, 578, 144-149.
34. Rubin, Y.; Parker, T. C.; Khan, S. I.; Holliman, C. L.; McElvany, S. W. J. Am. Chem. Soc. 1996, 118, 5308-5309.
35. (a) For organic dehydroannulenes see: Pak, J. J.; Weakley, T. J. R.; Haley, M. M. J. Am. Chem. Soc. 1999, 121, 8182-8192.
36. (b) Haley, M. M.; Pak, J. J.; Brand, S. C. Top. Curr. Chem. 1999, 121, 81-130.
37. Scott, L. T. In Modern Acetylene Chentistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim. 1996.
38. (a) Berscheid, R.; Vögtle, F. Synthesis 1992, 58-62.
39. (b) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657.
40. For the sensitivity of ferrocenes to the conditions of the copper-catalyzed alkyne-alkyne couplings see: Yuan, Z.; Stringer, G.; Jobe, I. R.; Kreller, D.; Scott, K; Koch, L.; Taylor, N. J.; Marder, T. B. J. Organomet. Chem. 1993, 452, 115-120.
41. (a) Bunz, U. H. F.; Enkelmann, V. Organometallics 1994, 13, 3823-3833.
42. (b) Bunz, U. H. F.; Enkelmann, V.; Räider, J. Organometallics 1993, 12, 4745-4747.
43. (c) Altmann, M.; Roidl, G.; Enkelmann, V.; Bunz, U. H. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 1107-1109.
44. (a) Jaufmann, J. D.; Case, C. B.; Sandor, R. B.; Foxman, B. M. J. Solid State Chem. 2000, 152, 99-104.
45. (b) Song, F.; Snook, J. H.; Foxman, B. M.; Snider, B. B. Tetrahedron 1998. 54, 13035-13044.
46. (a) Subramoney, S. Adv. Mater. 1998, 10, 1157-1171.
47. (b) Kroto, H. W. Nature 1992, 359, 670-671.
48. (c) Kutznetsov, V. L.; Chuvilin, A. L.; Moroz, E. M.; Kolomiichuk, V. N.; Shaikhutdinov, S. K.; Butenko, Y. V.; Malkov, I. Y. Carbon 1994, 32, 873-882.
49. (d) Thess, A.; Lee, R.; Nikolaev, P.; Dai, H. J.; Petit, P.; Robert, J.; Xu, C. H.; Lee, Y. H.; Kim, S. G.; Rinzler A. G.; Colbert, D. T.; Scuseria, G. E.; Tomanek, D.; Fischer, J. E.; Smalley, R. E. Science 1996, 273, 483-487.
50. (e) Ugarte, D. Nature 1992, 359, 707-709.
51. (f) Liu, J.; Dai, H. J.; Hafner, J. H.; Colbert, D. T.; Smalley, R. E.; Tans, S. J.; Dekker, C. Nature 1997, 385, 780-781.
52. (g) Selvan, R.; Unnikrishnan, R.; Ganapathy, S.; Pradeep, T. Chem. Phys. Lett. 2000, 316, 205-210.
53. De Heer, W. A.; Ugarte, D. Chem. Phys. Lett. 1993, 207, 480-486.
54. It is difficult to estimate yields by TEM but the ring-shaped nanostructures are almost everywhere. For a low magnification picture that gives an impression of the abundance of the nanostructures, see the Supporting Information.