Metallophthalocyanines: Versatile electron-donating building blocks for fullerene dyads

Journal of Physical Chemistry B

Volumn 108, Issue 48, 2004, Pages 18485-18494

  Guldi, Dirk M ^a,c   Zilbermann, Israel ^a   Gouloumis, Andreas ^b   Vázquez, Purificatión ^b   Torres, Tomás ^b  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^c UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE RECOMBINATION; METALLOPHTHALOCYANINES; PHOTOEXCITATION; PHYICOCHEMICAL PROPERTIES;

CHARGE TRANSFER; COPPER; ELECTROCHEMISTRY; ELECTRON TRANSITIONS; ENERGY TRANSFER; PHOTOSYNTHESIS; PHOTOVOLTAIC EFFECTS;

FULLERENES;

EID: 10644239157     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp047105z     Document Type: Article

References (64)

1. (a) The Photosynthetic Reaction Center; Deisenhofer, J., Norris, J. R., Eds.; Academic Press: New York, 1993.
2. (b) Molecular Mechanisms of Photosynthesis; Blankenship, R. E., Ed.; Blackwell Science, 2002.
3. (a) Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
4. (b) Turro, N. J. Modern Molecular Photo-chemistry; University Science Books: Mill Valley, CA, 1991; pp 321-361.
5. (c) Speiser, S. Chem. Rev. 1996, 96, 1953-1976.
6. (a) Gust, D.; Moore, T. A.; Moore, A. L.; Lee, S.-J.; Bittersmann, E.; Luttrull, D. K.: Rehms, A. A.; DeGraziano, J. M.; Ma, X. C.; Gao, F.; Belford, R. E.; Trier, T. T. Science 1990, 248, 199-201.
7. (b) Gust, D.; Moore, T. A.; Moore, A. L.; Macpherson, A. N.; Lopez, A.; DeGraziano, J. M.; Gouni, I.; Bittersmann, E.; Seely, G. R.; Gao, F.; Nieman, R. A.; Ma, X. C.; Demanche, L. J.; Hung, S.-C.; Luttrull, D. K.; Lee, S.-J.; Kerrigan, P. K. J. Am. Chem. Soc. 1993, 115, 11141-11152.
8. (c) Bennett, I. M.; Farfano, H. M. V.; Bogani, F.; Primak, A.; Liddell, P. A.; Otero, L.; Sereno, L.; Silber, J. J.; Moore, A. L.: Moore, T. A.; Gust, D. Nature 2002, 420, 398-401.
9. (a) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew, Chem., Int. Ed. 2000, 39, 3348-3391.
10. (b) Balzani, V.; Credi, A.; Venturi, M. In Stimulating Concepts in Chemistry; Vögtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, Germany, 2000.
11. (a) Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789-1791.
12. (b) Granström. M.; Petritsch, K.; Arias, A. C.; Lux, A.; Andersson, M. R.; Friend, R. H. Nature 1998, 395, 257-260.
13. (c) Brabec, C.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15-26.
14. (a) Phthalocyanines: Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH: Weinheim, Germany, 1989, 1993, 1996; Vols. 1-4.
15. (b) Hanack, M.; Heckmann, H.; Polley, R. In Methods in Organic Chemistry (Houben-Weyl); Schaumann, E., Ed.; Thieme: Stuttgart, 1998; Vol. E 9d, p 717.
16. (c) de la Torre, G.; Nicolau, M.; Torres, T. In Phthalocyanines: Synthesis, Supramolecular Organization and Physical Properties (Supramolecular Photosensitive and Electroactive Materials); Nalwa, H. S., Ed.; Academic Press: New York, 2001.
17. (d) Rodríguez-Morgade, M. S.; de la Torre, G.; Torres, T. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2003; Vol. 13.
18. (e) G. de la Torre, P.; Vázquez, F.; Agulló-López; Torres, T. Chem Rev. 2004, 104, 3723-3750.
19. Martínez-Díaz, M. V.; Esperanza, S.; de la Escosura, A.; Catenalli, M.; Yunus, S.; Luzzati, S.; Torres, T. Tetrahedron Lett. 2003, 44, 8475-8478.
20. (a) González-Cabello, A.; Vázquez, P.; Torres, T. Tetrahedron Lett. 1999, 40, 3263-3266.
21. (b) Gouloumis, A.; Liu, S.-G.; Vázquez, P.; Echegoyen, L.; Torres, T. Chem. Commun. 2001, 399-400.
22. (c) González-Cabello, A.; Vázquez, P.; Torres, T.: Guldi, D. M. J. Org. Chem. 2003, 68, 8635-8642.
23. Echegoyen, L.; Echegoyen, L. E. Ace. Chem. Res. 1998, 31, 593-601.
24. (a) The Chemistry of the Fullerenes; Hirsch, A., Ed.; Georg Thieme Verlag: Stuttgart, 1994.
25. (b) Science of Fullerenes and Carbon Nanotubes; Dresselhaus, M. S., Dresselhaus, G., Eklund, P. C., Eds.; Academic Press: San Diego, CA, 1996.
26. Fullerenes: from Synthesis to Optoelectronic Properties; Guldi, D. M., Martín, N., Eds.; Kluwer Academic Publishers: Dodrech, 2002.
27. (a) Imahori, H.; Sakata, Y. Adv. Mater. 1997, 9, 537-546.
28. (b) Prato, M. J. Mater. Chem. 1997, 7, 1097-1109.
29. (c) Martín, N.; Sánchez, L.: Illescas, B.; Pérez, I. Chem. Rev. 1998, 98, 2527-2547.
30. (d) Diederich, F.: Gómez-López, M. Chem. Soc. Rev. 1999, 28, 263-277.
31. (e) Imahori, H.; Sakata, Y. Eur. J. Org. Chem. 1999, 2445-2457.
32. (f) Guldi, D. M. Chem. Commun. 2000, 321-327.
33. (g) Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695-703.
34. (h) Reed, C. A.; Bolskar, R. D. Chem. Rev. 2000, 100, 1075-1120.
35. Gust, D.; Moore, T. A.; Moore, A. L. J. Photochem. Photobiol., B 2000, 58, 63-71.
36. (j) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40-48.
37. (k) Guldi, D. M. Chem. Soc. Rev. 2002, 31, 22-36.
38. (a) Linssen, T. G.; Durr, K.; Hanack, M.: Hirsch, A. J. Chem. Soc. Chem. Commun. 1995, 103-104.
39. (b) Durr, K.; Fiedler, S.; Linssen, T.; Hirsch, A,; Hanack, M. Chem. Ber. 1997, 130, 1375-1378.
40. (c) Sastre, A.; Gouloumis, A.; Vázquez, P.; Torres, T.; Doan, V.; Schwartz, B. J.; Wudl, F.; Echegoyen, L.; Rivera, J. Org. Lett. 1999, 1, 1807-1810.
41. (d) Martínez-Díaz, M. V.; Fender, N. S.; Rodríguez-Morgade, M. S.; Gómez-López, M.; Diederich, F.; Echegoyen, L.; Stoddart, J. F.; Torres, T. J. Mater. Chem. 2002, 12, 2095-2099.
42. (e) Guldi, D. M.; Ramey, J.; Martínez-Díaz, M. V.; de la Escosura, A.; Torres, T.; Da Ros, T.; Prato, M. Chem. Commun. 2002, 2774-2775.
43. (f) González-Rodríguez, D.; Torres, T. In The Exciting World of Nanocages and Nanotubes; Kamat, P., Guldi, D. M., Kadish, K., Eds.; Proc. Electrochem. Soc., Fullerenes; ECS: Pennington, NJ, 2002; Vol. 12, pp 195-210.
44. Gouloumis, A.; Liu, S.-G.; Sastre, A.; Vázquez, P.; Echegoyen, L. ; Torres, T. Chem. Eur. J. 2000, 6, 3600-3607.
45. Guldi, D. M.; Gouloumis, A.; Vázquez, P.; Torres, T. Chem. Commun. 2002, 2056-2057.
46. Loi, M. A.; Neugebauer, H.; Denk, P.; Brabec, C. J.; Sariciftci, N. S.; Gouloumis, A.; Vázquez, P.; Torres, T. J. Mater. Chem. 2003, 13, 700-704.
47. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
48. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L. Synthesis 1989, 47-48.
49. No correction was applied that accounts for electrostatic interactions in the dyads.
50. Kavarnos, G. J. Fundamentals of Photoinduced Electron Transfer, VCH-Wiley: New York, 1993.
51. Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695-703.
52. (a) Armaroli, N.; Marconi, G.; Echegoyen, L.; Bourgeois, J.-P.; Diederich, F. Chem. Eur. J. 2000, 6, 1629-1645.
53. (b) Imahori, H.; Tkachenko, N. V.; Vehmanen, V.; Tamaki, K.; Lemmetyinen, H.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2001, 105, 1750-11756.
54. (a) Smith, B. E.; Gouterman, M. Chem. Phys. Lett. 1968, 2, 517-519.
55. (b) Asano-Someda, M.; Sato, S.-I.; Aoyagi, K.; Kitagawa, T. J. Phys. Chem. 1995, 99, 13800-13807.
56. Asano-Someda, M.; Kaizu, Y. Photo-chem. Photobiol., A 1995, 87, 23-25.
57. (a) Oevering, H.; Paddon-Row: M. N.; Heppner, M.; Oliver, A. M.; Cotsaris, E.; Verhoeven, J. W.; Hush, N. S. J. Am. Chem. Soc. 1987, 109, 3258-3269.
58. (b) Marcus, R. A. J. Phys. Chem. 1989, 93, 3078-3086.
59. We still see the singlet transient.
60. (a) Marcus, R. A. Annu. Rev. Phys. Chem. 1964, 15, 155-159.
61. (b) Marcus, R. A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1111-1121.
62. (a) Fukuzumi, S. Org. Biomol. Chem. 2003, 8, 609-620.
63. (b) Kashiwagi, Y.; Ohkubo, K.; McDonal, J. A.; Blake, I. M.; Crossley, M. J.; Araki, Y.; Ito, O.; Imahori, H.; Fukuzumi, S. Org. Lett. 2003, 5, 2719-2721.
64. (c) Ohkubo, K.; Kotani, H.; Shao, J. G.; Ou, Z. P.; Kadish, K. M.; Li, G. L.; Pandey, R. K.; Fujitsuka, M.; Ito, O.; Imahori, H.; Fukuzumi, S. Angew. Chem. Int. Ed. 2004, 43, 853-856.