Facile preparation of doubly dipyrrolylquinoxaline-bridged expanded porphyrins. Synthesis and structural characterization of an unprecedented [20]tetraphyrin-(2.1.2.1)

Organic Letters

Volumn 8, Issue 11, 2006, Pages 2345-2348

  Szydlo, Florence ^a   Andrioletti, Bruno ^a   Rose, Eric ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33745683539     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0606381     Document Type: Article

References (21)

1. For a complete overview, see: The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: New York, 2000.
2. (a) Sessler, J. L.; Weghorn, S. J. In Expanded, Contracted and Isomeric Porphyrins; Elsevier Science Ltd.: Trowbridge, UK, 1997; Vol. 15.
3. (b) Jasat, A.; Dolphin, D. Chem. Rev. 1997, 97, 2267-2340.
4. (c) Sessler, J. L.; Seidel, D. Angew. Chem., Int. Ed. 2003, 42, 5134-5175.
5. See for instance: Charrière, R.; Jenny, T. A.; Rexhausen, H.; Gossauer, A. Heterocycles 1993, 36, 1561-1575.
6. Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17-55.
7. Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438-10439.
8. See for instance: (a) Anzenbacher, P.; Try, A. C.; Miyaji, H.; Jursíková, K.; Lynch, V. M.; Marquez, M.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 10268-10272.
9. (b) Pohl, R.; Aldakov, D.; Kubat, P.; Jursíková, K.; Marquez, M.; Anzenbacher, P. Chem. Commun. 2004, 1282-1283.
10. Sessler, J. L.; Maeda, H.; Mizuno, T.; Lynch, V. M.; Furuta, H. Chem. Commun. 2002, 862-863.
11. The only noticeable exception concerns the preparation of the diformyl DPQ (see ref 6).
12. Oddo, B. Gazz. Chim. Ital. 1911, 41, 248-255.
13. Szydlo, F.; Andrioletti, B.; Rose, E.; Duhayon, C. Tetrahedron Lett. 2004, 45, 7363-7365.
14. Sessler, J. L.; Andrioletti, B.; Anzenbacher, P., Jr.; Black, C.; Eller, L.; Furuta, H.; Jursíková, K.; Maeda, H.; Marquez, M.; Mizuno, T.; Try, A. In Fundamentals and Applications of Anion Separations; ACS Book ed.; Singh, R. P., Moyer, B. A., Eds.; Kluwer Academic/Plenum Publishers: New York, 2002.
15. (a) Sessler, J. L.; Brucker, E. A.; Weghorn, S. J.; Kisters, M.; Schafer, M.; Lex, J.; Vogel, E. Angew. Chem., Int. Ed. 1994, 33, 2308-2312.
16. (b) Aukauloo, M. A.; Guilard, R. New J. Chem. 1994, 18, 1205-1207.
17. (a) Falk, H. Monatsh. Chem. 1996, 129, 69-75.
18. (b) Neya, S.; Nishinaga, K.; Ohyama, K.; Funasaki, N. Tetrahedron Lett. 1998, 39, 5217-5220.
19. Unknown for oligopyrroles, the (2.1.2.1) arrangement was already reported in the thiophene and furan series.
20. 3 (a value in accordance with the volume of a small molecule, such as THF) and are located at the average positions 0.0 0.0 0.5 and 0.5 0.5 0.0 of the cell.
21. Král, V.; Sessler, J. L.; Zimmerman, R.; Seidel, D.; Lynch, V.; Andrioletti, B. Angew. Chem., Int. Ed. 2000, 39, 1055-1058.