Supramolecular control of oligothienylenevinylene-fullerene interactions: Evidence for a ground-state EDA complex

Organic Letters

Volumn 7, Issue 5, 2005, Pages 807-810

  McClenaghan, Nathan D ^a   Grote, Zacharias ^a   Darriet, Karine ^a   Zimine, Michael ^b   Williams, René M ^b   De Cola, Luisa ^b   Bassani, Dario M ^a  

^a CNRS   (France)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BARBITURIC ACID; FULLERENE DERIVATIVE; HYDROGEN; VINYL DERIVATIVE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL INTERACTION; DONOR; ELECTRON; ELECTRON TRANSPORT; HYDROGEN BOND; LIGHT; MOLECULAR SIZE; OXIDATION REDUCTION REACTION; REACTION TIME; SUBSTITUTION REACTION;

BARBITURATES; FULLERENES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; RECEPTORS, GABA-A; THIOPHENES;

EID: 15044356702     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047527r     Document Type: Article

References (28)

1. (a) Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
2. (b) Shaheen, S. E.; Brabec, J. C.; Padinger, F.; Fromherz, T.; Hummelen, J. C.; Sariciftci, N. S. Appl. Phys. Lett. 2001, 78, 841.
3. (c) Brabec, C. J.; Zerza, G.; Cerullo, G.; De Silvestri, S.; Luzzati, S.; Hummelen, J. C.; Sariciftci, N. S. Chem. Phys. Lett. 2001, 340, 232.
4. (d) Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474.
5. (a) Aperloo, J. J.; Martineau, C.; van Hal, P. A.; Roncali, J.; Janssen, R. A. J. J. Phys. Chem. A 2002, 106, 21.
6. (b) van Hal, P. A.; Beckers, E. H. A.; Meskers, S. C. J.; Janssen, R. A. J.; Jousselme, B.; Blanchard, P.; Roncali, J. Chem. Eur. J. 2002, 8, 5415.
7. (c) Beckers, E. H. A.; Schenning, A. P. H. J.; van Hal, P. A.; El-ghayoury, A.; Sánchez, L.; Hummelen, J. C.; Meijer, E. W.; Jansen, R. A. J. Chem. Commun. 2002, 2888.
8. (d) Solladié, N.; Walther, M. E.; Gross, M.; Figueira Duarte, T. M.; Bourgogne, C.; Nierengarten, J.-F. Chem. Commun. 2003, 2412.
9. (e) Segura, M.; Sánchez, L.; de Mendoza, J.; Martín, N.; Guldi, D. J. Am. Chem. Soc. 2003, 125, 15093.
10. (f) Li, K.; Schuster, D. I.; Guldi, D. M.; Herranz, M. A.; Echegoyen, L. J. Am. Chem. Soc. 2004, 126, 3388.
11. (g) Eckert, J.-F.; Byrne, D.; Nicoud, J.-F.; Oswald, L.; Nierengarten, J.-F.; Numata, M.; Ikeda, A.; Shinkai, S.; Armaroli, N. New J. Chem. 2000, 24, 749.
12. (a) Liddel, P. A.; Sumida, J. P.; Macpherson, A. N.; Moss, L.; Seely, G. R.; Clark, K. N.; Moore, T. A.; Gust, D. Photochem. Photobiol. 1994, 60, 537.
13. (b) Ayabe, M.; Ikeda, A.; Kubo, Y.; Takeuchi, M.; Shinkai, S. Angew. Chem., Int. Ed. 2002, 41, 2790.
14. (c) Guldi, D. M.; Hirsch, A.; Sceloske, M.; Dietel, E.; Troisi, A.; Zerbetto, F.; Prato, M. Chem. Eur. J. 2003, 9, 4968.
15. (d) Schuster, D. I.; Cheng, P.; Jarowski, P.; Guldi, D. M.; Luo, C.; Echegoyen, L.; Pyo, S.; Holzwarth, A. R.; Braslavsky, S. E.; Williams, R. M.; Klihm, G. J. Am. Chem. Soc. 2004, 126, 7257.
16. (e) Guldi, D. M.; Luo, C.; Prato, M.; Troisi, A.; Zerbetto, F.; Scheloske, M.; Dietel, E.; Bauer, W.; Hirsch, A. J. Am. Chem. Soc. 2001, 123, 9166.
17. (f) For a recent review of fullerene-porphyrin systems, see: El-Khouly, M. E.; Ito, O.; Smith, P. M.; D'Souza, F. J. Photochem. Photobiol. C: Rev. 2004, 5, 79.
18. (a) Datta, K.; Banerjee, M.; Seal, B. J.; Mukherjee, A. K. J. Chem. Soc., Perkin Trans. 2 2000, 531.
19. (b) Konarev, D. V.; Lyubovskaya, R. N.; Drichko, N. V.; Semkin, V. N.; Graja, A. Chem. Phys. Lett. 1999, 314, 570.
20. (c) Bhattacharya, S.; Nayak, S. K.; Chattopadhyay, S.; Banerjee, M.; Mukherjee, A. K. J. Phys. Chem. A 2001, 105, 9865.
21. (a) Sibley, S. S.; Campbell, R. L.; Silber, H. B. J. Phys. Chem. 1995, 99, 5274.
22. (b) Ohno, T.; Moriwaki, K.; Miyata, T. J. Org. Chem. 2001, 66, 3397.
23. McClenaghan, N. D.; Absalon, C.; Bassani, D. M. J. Am. Chem. Soc. 2003, 125, 13004.
24. (a) Chang, S.-K.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 1318.
25. (b) Dirksen, A.; Hahn, U.; Schwanke, F.; Reek, J. N. H.; Vögtle, F.; De Cola, L. Chem. Eur. J. 2004, 10, 2036.
26. Jestin, I.; Frère, P.; Mercier, N.; Levillain, E.; Stievenard, D.; Roncali, J. J. Am. Chem. Soc. 1998, 120, 8150.
27. The high-energy position of the band (2.75 eV, as deduced from the onset of the absorption) suggests that it involves orbitals other than the LUMO of 1 and the HOMO of 2.
28. 00 = 2.75 eV; see ref 2a.