Fused Polycyclic Aromatics via Electrophile-Induced Cyclization Reactions: Application to the Synthesis of Graphite Ribbons

Journal of the American Chemical Society

Volumn 116, Issue 17, 1994, Pages 7895-7896

  Goldfinger, Marc B ^a   Swager, Timothy M ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77953314667     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00096a056     Document Type: Article

References (18)

1. For other reports on graphite ribbons, see: Schlüter, A. D. Adv. Mater. 1991, 3, 282 and references therein
2. Koch, K. H.; Müllen, K. Chem. Ber. 1991, 124, 2091.
3. Grubbs, R. H.; Kratz, D. Chem. Ber. 1993, 126, 149.
4. For an example of a heterocyclic conjugated ladder polymer, see: Tour, J. M.; Lamba, J. J. S. J. Am. Chem. Soc. 1993, 115, 4935.
5. A graphite ribbon with a very similar architecture was recently reported: Chmil, K.; Scherf, U. Makromol. Chem., Rapid Commun. 1993, 14, 217.
6. This reaction affects a transformation similar to the Mallory photo-cyclization, which has been widely used in the synthesis of fused polycyclic aromatics. For a review, see: Mallory, F. B.; Mallory, C. W. Organic Reactions; Wiley & Sons: New York, 1984: Vol. 30, p 1.
7. Naarmann, H.; Theophilou, N. Synth. Met. 1987, 22, 1.
8. For examples of poly(p-phenylene)s prepared by cross-coupling chemistry, see: Rehahn, M.; Schlüter, A.-D.; Wegner, G.; Feast, W. J. Polymer 1989, 30, 1060.
9. Rehahn, M.; Schluter, A.-D.; Wegner, G. Makromol. Chem. 1990, 191, 1991.
10. Wallow, T. I.; Novak, B. M. J. Am. Chem. Soc. 1991, 113, 7411.
11. Scherf, U.; Müllen, K. Makromol. Chem., Rapid Commun. 1991, 12, 489.
12. Scherf, U.; Müllen, K. Macromolecules 1992, 25, 3546.
13. For a recent review on polyphenylenes, see: Tour, J. M. Adv. Mater. 1994, 6, 190.
14. Goldfinger, M. B.; Swager, T. M. Polym. Prepr., Am. Chem. Soc. Div. Polym. Chem. 1993, 34 (2), 755.
15. Barluenga, J.; Gonzalez, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319.
16. Barluanga, J.; Rodriguez, M. A.; Gonzalez, J. M.: Campos, P. J. Tetrahedron Lett. 1990, 31, 4207.
17. 4 with acetylenes and olefins to affect intramolecular carbocyclizations: Barluenga, J.; Gonzalez, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 1546.
18. 3 quench of phenyl-lithium which was prepared according to the literature: Trepka, W. J.; Sonnenfeld, R. J. J. Organomet. Chem. 1969, 16, 317.