Ground state electronic interactions in macrocyclic fullerene bis-adducts functionalized with bridging conjugated oligomers

European Journal of Organic Chemistry

Volumn , Issue 33, 2009, Pages 5779-5787

  Figueira Duarte, Teresa M ^a   Lloveras, Vega ^b   Vidal Gancedo, José ^b   Delavaux Nicot, Béatrice ^c   Duhayon, Carine ^c   Veciana, Jaume ^b   Rovira, Concepció ^b   Nierengarten, Jean François ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c CNRS   (France)

Author keywords

interactions; Conjugated oligomers; Electrochemistry; Fullerenes

Indexed keywords

EID: 72849121714     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900830     Document Type: Article

References (43)

1. J. L. Segura, N. Martin, D. M. Guldi, Chem. Soc. Rev. 2005, 34, 31-47.
2. T. M. Figueira-Duarte, A. Gégout, J.-F. Nierengarten, Chem. Commun. 2007, 109-119.
3. For selected, examples, see: E. Peeters, P. A. van Hal, J. Knol, C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, R. A. J. Janssen, J. Phys. Chem. B 2000, 104, 10174-10190;
4. N. Armaroli, F. Barigelletti, P. Ceroni, J.-F. Eckert, J.-F. Nicoud, J.-F. Nierengarten, Chem. Commun. 2000, 599-600;
5. D. M. Guldi, C. Luo, A. Swartz, R. Gomez, J. L. Segura, N Martin, C. Brabec, N. S. Sariciftci, J. Org. Chem. 2002, 67, 1141-1152;
6. A. M. Ramos, S. C. J. Meskers, P. A. van Hal, J. Knol, J. C. Hummelen, R. A. J. Janssen, J. Phys. Chem. A 2003, 107, 9269-9283;
7. M. Gutierrez-Nava, G. Accorsi, P. Masson, N. Armaroli, J.-F. Nierengarten, Chem. Eur. J. 2004, 10, 5076-5086;
8. D. M. Guldi, C. Luo, A. Swartz, R. Gomez, J. L. Segura, N. Martin, J. Phys. Chem. A 2004, 108, 455-467.
9. J.-F. Eckert, J.-F. Nicoud, J.-F. Nierengarten, S.-G. Liu, L. Echegoyen, F. Barigelletti, N. Armaroli, L. Ouali, V. Krasnikov, G. Hadziioannou, J. Am. Chem. Soc. 2000, 122, 7467-7479.
10. M. Kivala, C. Boudon, J.-P. Gisselbrecht, P. Seiler, M. Gross, F. Diederich, Chem. Commun. 2007, 4731-4733.
11. J. Anthony, A. M. Boldi, Y. Rubin, M. Hobi, V. Gramlich, C. B. Knobler, P. Seiler, F. Diederich, Helv. Chim. Acta 1995, 78, 13-45.
12. Metal-catalyzed Cross-coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998.
13. D. Felder, M. Gutiérrez Nava, M. del Pilar Carreon, J.-F. Eckert, M. Luccisano, C. Schall, P. Masson, J.-L. Gallani, B. Heinrich, D. Guillon, J.-F. Nierengarten, Helv. Chim. Acta 2002, 85, 288-319.
14. J.-F. Nierengarten, V. Gramlich, F. Cardullo, F. Diederich, Angew. Chem. Int. Ed. Engl. 1996, 35, 2101-2103;
15. J.-F. Nierengarten, T. Habicher, R. Kessinger, F. Cardullo, F. Diederich, V. Gramlich, J.-P. Gisselbrecht, C. Boudon, M. Gross, Helv. Chim. Acta 1997, 80, 2238-2276;
16. J.-F. Nierengarten, A. Herrmann, R. R. Tykwinski, M. Rüttimann, F. Diederich, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1997, 80, 293-316.
17. A. Gégout, M. Holler, T.M. Figueira-Duarte, J.-F. Nierengarten, Eur. J. Org. Chem. 2008, 3627-3634.
18. P. Nguyen, Z. Yuan, L. Agocs, G. Lesly, T. B. Maider, Inorg. Chim. Acta 1994, 220, 289-296.
19. J.-P. Bourgeois, F. Diederich, L. Echegoyen, J.-F. Nierengarten, Helv. Chim. Acta 1998, 81, 1835-1844;
20. J.-F. Nierengarten, C. Schall, J.-F. Nicoud, Angew. Chem. Int. Ed. 1998, 37, 1934-1936.
21. D. I. Schuster, P. D. Jarowski, A. N. Kirschner, S. R. Wilson, J. Mater. Chem. 2002, 12, 2041-2047;
22. N. Armaroli, G. Marconi, L. Echegoyen, J.-P. Bourgeois, F. Diederich, Chem. Eur. J. 2000, 6, 1629-1645;
23. N. Solladié, M. E. Walther, M. Gross, T. M. Figueira-Duarte, C. Bourgogne, J.-F. Nierengarten, Chem. Commun. 2003, 2412-2413;
24. N. Armaroli, G. Accorsi, F. Song, A. Palkar, L. Echegoyen, D. Bonifazi, F. Diederich, ChemPhysChem 2005, 6, 732-743;
25. P. D. W. Boyd, C. A. Reed, Acc. Chem. Res. 2005, 38, 235-242, and references cited therein.
26. J. Santos, B. Grimm, B. M. Illescas, D. M. Guldi, N. Martin, Chem. Commun. 2008, 5993-5995.
27. F. Cardullo, P. Seiler, L. Isaacs, J.-F. Nierengarten, R. F. Haldimann, F. Diederich, T. Mordasini-Denti, W. Thiel, C. Boudon, J.-P. Gisselbrecht, M. Gross, Helv. Chim. Acta 1997, 80, 343-371;
28. Y. Rio, G. Enderlin, C. Bourgogne, J.-F. Nierengarten, J.-P. Gisselbrecht, M. Gross, G. Accorsi, N. Armaroli, Inorg. Chem. 2003, 42, 8783-8793;
29. U. Hahn, E. Maisonhaute, C. Amatare, J.-F. Nierengarten, Angew. Chem. Int. Ed. 2007, 46, 951-954;
30. R. Pereira de Freitas, J Iehl, B. Delavaux-Nicot, J.-F. Nierengarten, Tetrahedron 2008, 64, 11409-11419.
31. T. M. Figueira-Duarte, V. Lloveras, J. Vidal-Gancedo, A. Gégout, B. Delavaux-Nicot, R. Welter, J. Veciana, C. Rovira, J.-F. Nierengarten, Chem. Commun. 2007, 4345-4347.
32. E. Ahlberg, B. Helgee, V. D. Parker, Acta Chem. Scand., Ser. B 1980, 34, 187-193.
33. S. Sumalekshmy, K. R. Gopidas, Chem. Phys. Lett. 2005, 413, 294-299.
34. M. Robin, P. Day, Adv. Inorg. Radiochem. 1967, 10, 247-422.
35. N. S. Hush, Coord. Chem. Rev. 1985, 64, 135-157;
36. R. J. Cave, M. D. Newton, J. Chem. Phys. 1997, 106, 9213-9226.
37. Y Rio, G. Accorsi, H. Nierengarten, J.-L. Rehspringer, B. Hönerlage, G. Kopitkovas, A. Chugreev, A. Van Dorsselaer, N. Armaroli, J.-F. Nierengarten, New J. Chem. 2002, 26, 1146-1154;
38. Y. Rio, G. Accorsi, H. Nierengarten, C. Bourgogne, J.-M. Strub, A. Van Dorsselaer, N. Armaroli, J.-F. Nierengarten, Tetrahedron 2003, 59, 3833-3844;
39. U. Hahn, M. Elhabiri, A. Trabolsi, H. Herschbach, E. Leize, A. Van Dorsselaer, A.-M. Albrecht-Gary, J.-F. Nierengarten, Angew. Chem. Int. Ed. 2005, 44, 5338-5341;
40. J.-F. Nierengarten, U. Hahn, A. Trabolsi, H. Herschbach, F. Cardinali, M. Elhabiri, E. Leize, A. Van Dorsselaer, A.-M. Albrecht-Gary, Chem. Eur. J. 2006, 12, 3365-3373.
41. A. Altomare, G. Cascarano C. Giacovazzo, A. Guagliardi, J. Appl. Crystallogr. 1993, 26, 343-350.
42. P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J Watkin, J. Appl. Crystallogr. 2003, 36, 1487.
43. International Tables for X-ray Crystallography, Kynoch Press, Birmingham, U.K., 1974, vol. IV.