Polyethynylated cyclic π-systems: scaffoldings for novel two and three-dimensional carbon networks

Abstract

All-carbon materials with novel topologies are of interest in regard to their materials properties. These novel structures include graphite-like two-dimensional networks as well as fullerene-like three-dimensional cages. This article reviews recent developments in the synthesis of scaffolds for novel forms of carbon made of a core π-system carrying alkyne appendages, such as hexaethynylbenzene and its derivatives, pentaethynylcyclopentadienyl metal complexes, and tetraethynylcyclobutadiene metal complexes. Also included are the syntheses and properties of macrocyclic π-systems derived of these units which represent important substructures for the infinite lattices of novel carbon allotropes.

References

1. F. Diederich and Y. Rubin, Angew. Chem., Int. Ed. Engl., 1992, 31, 1101.
2. F. Diederich, Nature, 1994, 369, 199.
3. R. H. Baughman, H. Eckhardt and M. J. Kertesz, J. Chem. Phys., 1987, 87, 6687.
4. M. M. Haley, S. C. Brand and J. J. Pak, Angew. Chem., Int. Ed. Engl., 1997, 36, 836.
5. U. H. F. Bunz and V. Enkelmann, Organometallics, 1994, 13, 3823.
6. R. H. Baughman, D. S. Galvão, C. Cui, Y. Wang and D. Tománek, Chem. Phys. Lett., 1993, 204, 8.
7. U. H. F. Bunz, V. Enkelmann and F. Beer, Organometallics, 1995, 14, 2490.
8. Y. Rubin, Chem. Eur. J., 1997, 3, 1009.
9. For a review on tetraethynylethylene, belonging to another class of scaffolds consisting of only sp² and sp carbons, see; R. R. Tykwinski and F. Diederich, Liebigs Ann./Rec., 1997, 649.
10. R. Diercks, J. C. Armstrong, R. Roese and K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 1986, 25, 268.
11. R. Böse, J. R. Green, J. Mittendorf, D. L. Möhler and K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 1992, 31, 1643.
12. K. Praefcke, B. Kohne and D. Singer, Angew. Chem., Int. Ed. Engl., 1990, 29, 177.
13. K. Kondo, S. Yasuda, T. Sakaguchi and M. Miya, J. Chem. Soc., Chem. Commun., 1995, 55.
14. J. E. Anthony, S. I. Khan and Y. Rubin, Tetrahedron Lett., 1997, 38, 3499.
15. Y. Tobe, K. Kubota and K. Naemura, J. Org. Chem., 1997, 62, 3430.
16. J. D. Tovar, N. Jux, T. Jarrosson, S. I. Kahn and Y. Rubin, J. Org. Chem., 1997, 62, 3432.
17. N. Jux, K. Holczer and Y. Rubin, Angew. Chem., Int. Ed. Engl., 1996, 35, 1986.
18. Y. Rubin, T. C. Parker, S. I. Kahn, C. L. Holliman and S. W. McElvany, J. Am. Chem. Soc., 1996, 118, 5308.
19. Y. Rubin, T. C. Parker, S. J. Pastor, S. Jalistagi, C. Boulle and C. L. Wilkins, Angew. Chem., Int. Ed., 1998, 37, 1226.
20. Y. Tobe, N. Nakagawa, K. Naemura, T. Wakabayashi, T. Shida and Y. Achiba, J. Am. Chem. Soc., 1998, 120, 4544.
21. N. S. Goroff, Acc. Chem. Res., 1996, 29, 77.
22. U. H. F. Bunz, V. Enkelmann and J. Räder, Organometallics, 1993, 12, 4745.
23. U. H. F. Bunz and V. Enkelmann, Angew. Chem., Int. Ed. Engl., 1993, 32, 1653.
24. U. H. F. Bunz and V. Enkelmann, Organometallics, 1994, 13, 3823.
25. J. R. Fitch and K. P. C. Vollhardt, Organometallics, 1992, 1, 590.
26. M. Altmann, G. Roidl, V. Enkelmann and U. H. F. Bunz, Angew. Chem., Int. Ed. Engl., 1997, 36, 1107.
27. I. D. Campbell, G. Eglinton, W. Henderson and R. A. Raphael, J. Chem. Soc., Chem. Commun., 1966, 87.
28. H. A. Staab and F. Graf, Helv. Chim. Acta, 1970, 103, 1107.
29. C. Huynh and G. Linstrumelle, Tetrahedron, 1988, 44, 6337.
30. M. Iyoda, A. Vorasingha, Y. Kuwatani and M. Yoshida, Tetrahedron Lett., 1998, 39, 4701.
31. D. Malaba, A. Djebli, L. Chen, E. A. Zarate, C. A. Tessier and W. J. Youngs, Organometallics, 1993, 12, 1266.
32. J. D. Ferrara, A. A. Tanaka, C. Fierro, C. A. Tessier-Youngs and W. J. Youngs, Organometallics, 1989, 8, 2089.
33. J. D. Ferrara, A. Djebli, C. A. Tessier-Youngs and W. J. Youngs, J. Am. Chem. Soc., 1988, 110, 647.
34. C. Eickmeier, H. Junga, A. J. Matzher, F. Scherhag, M. Shim and K. P. C. Vollhardt, Angew. Chem., Int. Ed. Engl., 1997, 36, 2103.
35. Q. Zhou, P. J. Carroll and T. M. Swager, J. Org. Chem., 1994, 59, 1294.
36. M. M. Haley, M. L. Bell, J. J. English, C. A. Johnson and T. J. R. Weakley, J. Am. Chem. Soc., 1997, 119, 2956.
37. U. H. F. Bunz and J. E. C. Wiegelmann-Kreiter, Chem. Ber., 1996, 129, 785.
38. M. Altmann, J. Friedrich, F. Beer, R. Reuter, V. Enkelmann and U. H. F. Bunz, J. Am. Chem. Soc., 1997, 119, 1472.