Facile synthesis of Janus "double-concave" tribenzo[a,g,m] coronenes

Journal of Organic Chemistry

Volumn 72, Issue 10, 2007, Pages 3917-3920

  Li, Zhongtao ^a   Lucas, Nigel T ^b   Wang, Zhaohui ^a   Zhu, Daoben ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

GUEST MOLECULES; HEXABUTOXYTRIBENZO[A,G,M]CORONENES; HEXABUTOXYTRIPHENYLENE; SINGLE-CRYSTAL X-RAY DIFFRACTION;

AROMATIC COMPOUNDS;

CORONENE; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLIZATION; HYDROGENATION; MOLECULE; SUZUKI REACTION; SYNTHESIS; X RAY DIFFRACTION;

EID: 34248581896     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0701029     Document Type: Article

References (37)

1. (a) Clar, E. Polycyclic Hydrocarbons; Academic Press: London, UK, 1964. For recent reviews:
2. (b) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267.
3. (c) Grimsdale, A. C.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 5592.
4. (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
5. (b) Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359.
6. See examples: (a) Duong, H. M.; Bendikov, M.; Steiger, D.; Zhang, Q.; Sonmez, C.; Yamada, J.; Wudl, F., Org. Lett. 2003, 5, 4433.
7. (b) Shibata, K.; Kulkarni, A. A.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1994, 116, 5983.
8. (c) Kobayashi, N.; Fukuda, T.; Ueno, K.; Ogino, H. J. Am. Chem. Soc. 2001, 123, 10740.
9. (a) Boorum, M. M.; VasilPev, Y. V.; Drewello, T.; Scott, L. T. Science 2001, 294, 828.
10. (b) Scott, L. T.; Boorum, M. M.; McMahon, B. J.; Hagen, S.; Mack, J.; Blank, J.; Wegner, H.; de Meijere, A. Science 2002, 295, 1500.
11. (c) Scott, L. T. Pure Appl. Chem. 1996, 68, 291.
12. (a) Wang, Z.; Dötz, F.; Enkelmann, V.; Müllen, K. Angew. Chem., Int. Ed. 2005, 44, 1247.
13. (b) Mizyed, S.; Georghiou, P.; Bancu, M.; Cuadra, B.; Rai, A. K.; Cheng, P.; Scott, L. T. J. Am. Chem. Soc. 2001, 123, 12770.
14. (c) Petrukhina, M. A.; Andreini, K. W.; Peng, L.; Scott, L. T. Angew. Chem., Int. Ed. 2004, 43, 5477.
15. (d) Sakurai, H.; Daiko, T.; Sakane, H.; Amaya, T.; Hirao, T. J. Am. Chem. Soc. 2005, 127, 11580.
16. Xiao, S.; Myers, M.; Miao, Q.; Sanaur, S.; Pang, K.; Steigerwald, M. L.; Nuckolls, C. Angew. Chem., Int. Ed. 2005, 44, 7390.
17. (a) Sygula, A.; Karlen, S. D.; Sygula, R.; Rabideau, P. W. Org. Lett. 2002, 4, 3135.
18. (b) Kim, D.; Petersen, J. L.; Wang, K. K. Org. Lett. 2006, 8, 2313.
19. (c) Reisch, H. A.; Bratcher, M. S.; Scott, L. T. Org. Lett. 2000, 2, 1427.
20. (d) Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 2000, 122, 6323.
21. (e) Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 380.
22. (f) Rabideau, P. W.; Abdourazak, A. H.; Folsom, H. E.; Marcinow, Z.; Sygula, A.; Sygula, R. J. Am. Chem. Soc. 1994, 116, 7891.
23. (g) Sakurai, H.; Daiko, T.; Hirao, T. Science 2003, 301, 1878.
24. (a) Piatelli, M; Fattorusso, E.; Nicholaus, R. A.; Magno, S. Tetrahedron 1965, 21, 3229.
25. (b) Markovitsi, D.; Germain, A.; Millie, P.; Lecuyer, P.; Gallos, L. K. J. Phys. Chem. 1995, 99, 1005.
26. Boden, N.; Bushby, R. J.; Cammidge, A. N.; Duckworth, S.; Headdock, G. J. Mater. Chem. 1997, 7, 601.
27. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
28. (b) Tellenbröker, J.; Kuck, D. Angew. Chem., Int. Ed. 1999, 38, 919.
29. (a) Boden, N.; Bushby, R. J.; Cammidge, A. N. J. Chem. Soc., Chem. Commun. 1994, 465.
30. (b) Wang, Z.; Watson, M. D.; Wu, J.; Müllen, K. Chem. Commun. 2004, 336.
31. Sofer, H.; Polansky, O. E.; Derfling, G. Monatsh. Chem. 1968, 99, 1879.
32. Fujioka, Y. Bull. Chem. Soc. Jpn. 1984, 57, 3439.
33. Fujioka, Y. Bull. Chem. Soc. Jpn. 1985, 58, 481.
34. Clar, E. The Aromatic Sextet; Wiley: London, UK, 1972.
35. Data collection was carried out on a Rigaku diffractometer with a Saturn CCD area detector. The structure was solved by direct methods in SHELXS-97.
36. Wang, Z.; Tomovic, Z.; Kastler, M.; Pretsch, R.; Negri, F.; Enkelmann, V.; Müllen, K. J. Am. Chem. Soc. 2004, 126, 7794.
37. Zhang, Q.; Prins, P.; Jones, S. C.; Barlow, S.; Kondo, T.; An, Z.; Siebbeles, L. D. A.; Marder, S. R. Org. Lett. 2005, 7, 5019.