Synthesis and photoelectrochemical properties of a fullerene- azothiophene dyad

Journal of Materials Chemistry

Volumn 9, Issue 11, 1999, Pages 2743-2750

  Cattarin, Sandro ^a   Ceroni, Paola ^b   Guldi, Dirk M ^c   Maggini, Michele ^d   Menna, Enzo ^d   Paolucci, Francesco ^b   Roffia, Sergio ^b   Scorrano, Gianfranco ^d  

^a Ist Polarografia ed E   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF NOTRE DAME   (United States)

^d UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; FULLERENE; THIOPHENE DERIVATIVE;

ARTICLE; ELECTROCHEMISTRY; ELECTRON TRANSPORT; MOLECULAR DYNAMICS; PHOTOCHEMISTRY; SYNTHESIS; THERMODYNAMICS;

EID: 0032701272     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905287i     Document Type: Article

References (48)

1. 1 Fullerenes and Related Structures, Ed. A. Hirsch, Series: Topics in Current Chemistry, Springer-Verlag, Berlin/Heidelberg, 1998, Vol. 199.
2. 2 A. W. Jensen, S. R. Wilson and D. I. Schuster, Bioorg. Med. Chem., 1996, 4, 767.
3. 3 M. Prato, J. Mater. Chem., 1997, 7, 1097.
4. 4 C. S. Foote, Top. Curr. Chem., 1994, 169, 347.
5. 5 (a) H. Imahori and Y. Sakata, Adv. Mater., 1997, 9, 537;
6. (b) N. Martin, L. Sanchez, B. Illescas and I. Perez, Chem. Rev., 1998, 98, 2527;
7. (c) J. F. Nierengarten, C. Schall and J. F. Nicoud, Angew. Chem., Int. Ed. Engl., 1998, 37, 1934;
8. (d) M. Maggini, D. M. Guldi, S. Mondini, G. Scorrano, F. Paolucci, P. Ceroni and S. Roffia, Chem. Eur. J., 1998, 4, 1992;
9. (e) E. Dietel, A. Hirsch, E. Eichhorn, A. Rieker, S. Hackbarth and B. Roder, Chem. Commun., 1998, 21, 1981;
10. (f) D. M. Guldi, G. Torres Garcia and J. Mattay, J. Phys. Chem., 1998, 102, 9679;
11. (g) S. Higashida, H. Imahori, T. Kaneda and Y. Sakata, Chem. Lett., 1998, 7, 605;
12. (h) K. Tamaki, H. Imahori, Y. Nishimura, I. Yamazaki and Y. Sakata, Chem. Commun., 1999, 7, 625;
13. (i) K. Tamaki, H. Imahori, Y. Nishimura, I. Yamazaki, A. Shimomura, T. Okada and Y. Sakata, Chem. Lett., 1999, 3, 227;
14. (j) J. F. Nierengarten, J. F. Eckert, J. F. Nicoud, L. Ouali, V. Krasnikov and G. Hadziioannou, Chem. Commun., 1999, 7, 617;
15. (k) N. Armaroli, F. Diederich, L. Echegoyen, T. Habicher, L. Flamigni, G. Marconi and J. F. Nierengarten, New J. Chem., 1999, 23, 77;
16. (l) A. Polese, S. Mondini, A. Bianco, C. Toniolo, G. Scorrano, D. M. Guldi and M. Maggini, J. Am. Chem. Soc., 1999, 121, 3446;
17. (m) P. Cheng, S. R. Wilson and D. I. Schuster, Chem. Commun., 1999, 7, 89;
18. (n) T. Da-Ros, M. Prato, D. Guldi, E. Alessio, M. Ruzzi and L. Pasimeni, Chem. Commun., 1999, 7, 635;
19. (o) S.-J. Liu, L. Shu, J. Rivera, H. Liu, J.-M. Raimundo, J. Roncali, A. Gorgues and L. Echegoyen, J. Org. Chem., 1999, 64, 4884.
20. 6 N. S. Sariciftci, L. Smilowitz, A. J. Heeger and F. Wudl, Science, 1992, 258, 1474.
21. 7 The azothiophene chromophore was used, instead of the more conventional azobenzenes, mainly because aldehyde 1, precursor to fulleropyrrolidine 2, was readily available from BASF-AG (see Experimental section).
22. 8 A. Hagfeldt and M. Grätzel, Chem. Rev., 1995, 95, 49.
23. 9 P. Bonhôte, J.-E. Moser, R. Humphry-Baker, N. Vlachopoulos, S. M. Zakeeruddin, L. Walder and M. Grätzel, J. Am. Chem. Soc., 1999, 121, 1324.
24. 10 C. Luo, C. Huang, L. Gan, D. Zhou, W. Xia, Q. Zhuang, Y. Zhao and Y. Huang, J. Phys. Chem., 1996, 100, 16 685.
25. 11 G. Franco, J. Gehring, L. M. Peter, E. A. Ponomarev and I. Uhlendorf, J. Phys. Chem. B, 1999, 103, 692.
26. 12 A. Bianco, M. Maggini, G. Scorrano, C. Toniolo, G. Marconi, C. Villani and M. Prato, J. Am. Chem. Soc., 1996, 118, 4072.
27. 13 D. Guldi, M. Maggini, G. Scorrano and M. Prato, J. Am. Chem. Soc., 1997, 119, 974.
28. 14 M. Maggini, G. Scorrano and M. Prato, J. Am. Chem. Soc., 1993, 115, 9798.
29. 15 M. K. Nazeeruddin, A. Kay, I. Rodicio, R. Humphry-Baker, E. Müller, P. Liska, N. Vlachopoulos and M. Grätzel, J. Am. Chem. Soc., 1993, 115, 6382.
30. 16 J. C. Hummelen, B. Knight, J. Pavlovich, R. Gonzalez and F. Wudl, Science, 1995, 269, 1554.
31. 17 E. L. Yee, R. J. Cave, K. L. Guyer, P. D. Tyma and M. J. Weaver, J. Am. Chem. Soc., 1979, 101, 1131.
32. 18 N. Vlachopoulos, P. Liska, J. Augunstinski and M. Grätzel, J. Am. Chem. Soc., 1988, 110, 1216.
33. 19 M. Prato and M. Maggini, Acc. Chem. Res., 1998, 31, 519.
34. -1).
35. 21 J. P. Stradins and V. T. Glezer, in Encyclopedia of Electrochemistry of the Elements, Organic Section, Ed. A. J. Bard and H. Lund, Marcel Dekker, Inc., New York, 1979, Vol. XIII, p. 163.
36. 22 J. Roncali, Chem. Rev., 1992, 92, 711.
37. 23 M. G. Hutchings, P. Gregory, J. S. Campbell, A. Strong, J.-P. Zamy, A. Lepre and A. Mills, Chem. Eur. J., 1997, 3, 1719.
38. 24 The azobenzene moiety is known to undergo trans-cis isomerization. However, for the dye 3 no photochemical reaction was observed upon excitation both in the visible and in the UV spectral region.
39. 25 The fluorescence spectrum of 2 at 77 K shows both the dye-and the fullerene-based emission.
40. 1dye* state were used in thecalculations. (a) A. Z. Weller, Phys. Chem. (Wiesbaden), 1982, 93, 1982; (b) H. Imahori, K. Hagiwara, M. Aoki, T. Akiyama, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata, J. Am.Chem. Soc., 1996, 118, 11 771; (c) S. I. van Dijk, C. P. Groen, F. Hartl, A. Brouwer and J. W. Verhoeven, J. Am. Chem. Soc., 1996, 118, 8425.
41. 1dye* state were used in thecalculations. (a) A. Z. Weller, Phys. Chem. (Wiesbaden), 1982, 93, 1982; (b) H. Imahori, K. Hagiwara, M. Aoki, T. Akiyama, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata, J. Am. Chem. Soc., 1996, 118, 11 771; (c) S. I. van Dijk, C. P. Groen, F. Hartl, A. Brouwer and J. W. Verhoeven, J. Am. Chem. Soc., 1996, 118, 8425.
42. 1dye* state were used in thecalculations. (a) A. Z. Weller, Phys. Chem. (Wiesbaden), 1982, 93, 1982; (b) H. Imahori, K. Hagiwara, M. Aoki, T. Akiyama, S. Taniguchi, T. Okada, M. Shirakawa and Y. Sakata, J. Am.Chem. Soc., 1996, 118, 11 771; (c) S. I. van Dijk, C. P. Groen, F. Hartl, A. Brouwer and J. W. Verhoeven, J. Am. Chem. Soc., 1996, 118, 8425.
43. 27 The spectral features of the charge-separated radical pair and the lifetime of the latter resembled those observed upon the dye excitation (535 nm).
44. 28 Analogously, radiation-induced reduction of dyad 2 in toluenepropan-2-ol-acetone solution resulted in a distinct NIR absorption at 1010 nm.
45. 29 Q. Xie, F. Arias and L. Echegoyen, J. Am. Chem. Soc., 1993, 115, 9818.
46. 30 A. Wahl, M. Ulmann, A. Carroy, B. Jermann, M. Dolata, P. Kedzierzawski, C. Chatelain, A. Monnier and J. Augusynsky, J. Electroanal. Chem., 1995, 396, 41.
47. 31 R. Dabestani, A. J. Bard, A. Campion, M. A. Fox, T. E. Mallouk, S. E. Webber and J. M. White, J. Phys. Chem., 1988, 92, 1872.
48. 32 G. K. Boschloo and A. Goossens, J. Phys. Chem., 1996, 100, 19 489.