Stabilization of charge-separated states in phthalocyanine-fullerene ensembles through supramolecular donor-acceptor interactions

Journal of the American Chemical Society

Volumn 128, Issue 12, 2006, Pages 4112-4118

  De La Escosura, Andrés ^a   Martínez Díaz, M Victoria ^a   Guldi, Dirk M ^b   Torres, Tomás ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHEMICAL BONDS; DERIVATIVES; ELECTRONIC COMMUNITIES; FULLERENES; GROUND STATE; LEAD; NITROGEN; OXIDATION; STABILIZATION; ZINC;

AZOMETHINE YLIDES; DONOR-ACCEPTOR INTERACTIONS; PHENYLENEVINYLENE SPACER; SUPRAMOLECULAR TRIADS;

SUPRAMOLECULAR CHEMISTRY;

4 VINYLBENZALDEHYDE; AZOMETHINE YLIDE; BENZALDEHYDE DERIVATIVE; CARBON; FULLERENE; PHENYLENEVINYLENE; PHTHALOCYANINE ZINC; SARCOSINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; CYCLOADDITION; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; HECK REACTION; INFRARED SPECTROSCOPY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OXIDATION; PHOTOREACTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

BIOMIMETIC MATERIALS; CARBOXYLIC ACIDS; FULLERENES; INDOLES; ORGANOMETALLIC COMPOUNDS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; ZINC;

EID: 33645463688     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja058123c     Document Type: Article

References (50)

1. (a) The Photosynthetic Reaction Center; Deisenhofer, J., Norris, J. R., Eds.; Academic Press: New York, 1993.
2. (b) The Reaction Center of Photosynthetic Bacteria; Michel-Beyerle, M. E., Ed.; Springer: Berlin, 1996.
3. (a) Hoeben, F. J. M.; Johkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546.
4. (b) Konishi, T.; Ikeda, A.; Shinkai, S. Tetrahedron 2005, 61, 4881-4899.
5. (c) Bonnett, R.; Martínez, G. Tetrahedron 2001, 57, 9513-9547.
6. (a) Wasielewski, M. A. Chem. Rev. 1992, 92, 435-461.
7. (b) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205.
8. (c) Harriman, A.; Sauvage, J.-P. Chem. Soc. Rev. 1996, 25, 41-48.
9. (d) Choi, M.-S.; Yamazaki, T.; Yamazaki, I.; Aida, T. Angew. Chem., Int. Ed. 2004, 43, 150-158.
10. (e) Ozeki, H.; Nomoto, A.; Ogawa, K.; Kobuke, Y.; Murakami, M.; Hosoda, K.; Ohtani, M.; Nakashima, S.; Miyasaka, H.; Okada, T. Chem. Eur. J. 2004, 10, 6393-6401.
11. (f) Balaban, T. S. Acc. Chem. Res. 2005, 38, 612-623.
12. (a) Guldi, D. M. Chem. Soc. Rev. 2002, 31, 22-36.
13. (b) Guldi, D. M. Chem. Commun. 2000, 321-327.
14. (c) Guldi, D. M.; Prato, M. Acc. Chem. Res. 2000, 33, 695-703.
15. (d) Fullerene and Related Structures; Hirsch, A., Ed.; Springer: Berlin, 2005.
16. (a) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guillard, R., Eds.; Academic Press: San Diego, 2003; Vols. 15-20.
17. (b) Hanack, M.; Heckmann, H.; Polley, R. In Methods in Organic Chemistry; Schaumann, E., Ed.; Thieme: Stuttgart, 1998; Vol. E 9d, p 717.
18. (c) de la Torre, G.; Nicolau, M.; Torres, T. In Phthalocyanines: Synthesis, Supramolecular Organization and Physical Properties; Nalwa, H. S., Ed.; Academic Press: New York, 2001.
19. (d) de la Torre, G.; Vázquez, P.; Agulló-López, F.; Torres, T. J. Mater. Chem. 1998, 8, 1671-1683.
20. (e) de la Torre, G.; Vázquez, P.; Agulló-López, F.; Torres, T. Chem. Rev. 2004, 104, 3723-3750.
21. (a) Gouloumis, A.; Liu, S.-G.; Sastre, A.; Vázquez, P.; Echegoyen, L.; Torres, T. Chem. Eur. J. 2000, 6, 3600-3607.
22. (b) Gouloumis, A.; Liu, S.-G.; Vázquez, P.; Echegoyen, L.; Torres, T. Chem. Commun. 2001, 399-400.
23. (c) González-Cabello, A.; Vázquez, P.; Torres, T.; Guldi, D. M. J. Org. Chem. 2003, 68, 8635-8642.
24. (d) González-Rodríguez, D.; Torres, T.; Herranz, M. A.; Rivera, J.; Echegoyen, L.; Guldi, D. M. J. Am. Chem. Soc. 2004, 126, 6301-6313.
25. (a) D'Souza, F.; Deviprasad, G. R.; Zandler, M. E.; Hoang, V. T.; Klykov, A.; Van Stipdonk, M.; Perera, A.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O. J. Phys. Chem. A 2002, 106, 3243.
26. (b) D'Souza, F.; Smith, P. M.; Gaddle, S.; McCarty, A. L.; Kullman, M. J.; Zandler, M. E.; Itou, M.; Araki, Y.; O. Ito, O. J. Phys. Chem. B 2004, 108, 11333.
27. (c) Da Ros, T.; Prato, M.; Carano, M.; Ceroni, P.; Paolucci, F.; Bofia, S.; Valli, L.; Guldi, D. M. J. Organomet. Chem. 2000, 509, 62.
28. (d) Da Ros, T.; Prato, M.; Guldi, D. M.; Ruzzi, M.; Pasimeni, L. Chem. Eur. J. 2001, 7, 816.
29. (e) Guldi, D. M.; Martín, N. J. Mater. Chem. 2002, 12, 1978-1992.
30. (f) Boyd, P. D. W.; Reed, C. A. Acc. Chem. Res. 2005, 38, 235-242.
31. (g) Sessler, J. L.; Jayawickramarajah, J.; Gouloumis, A.; Torres, T.; Guldi, D. M.; Maldonado, S.; Stevenson, K. J. Chem. Commun. 2005, 1892.
32. (a) 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.
33. (b) 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.
34. (c) Guldi, D. M.; Gouloumis, A.; Vázquez, P.; Torres, T.; Georgakilas, V.; Prato, M. J. Am. Chem. Soc. 2005, 127, 5811-5813.
35. de la Escosura, A.; Martínez-Díaz, M. V.; Thordarson, P.; Rowan, A. E.; Nolte, R. J. M.; Torres, T. J. Am. Chem. Soc. 2003, 125, 12300-12308.
36. Loi, M. A.; Denk, P.; Hoppe, H.; Neugebauer, H.; Winder, C.; Meissner, D.; Brabec, C.; Sariciftci, N. S.; Gouloumis, A.; Vázquez, P.; Torres, T. J. Mater. Chem. 2003, 13, 700.
37. Fluorescence quantum yield = 0.3; fluorescence lifetime = 3.1 ± 0.2 ns.
38. Kameyama, K.; Morisue, M.; Satake, A.; Kobuke, Y. Angew. Chem., Int. Ed. 2005, 44, 4763-4766.
39. 1H NMR spectrum of compound 3 in the Supporting Information).
40. Bruneau, E.; Lavabre, D.; Levy, G.; Micheau, J. C. J. Chem. Educ. 1992, 69, 833.
41. Klausen, K. S. Anal. Chim. Acta 1969, 44, 377.
42. The same experiment was carried out for the reference donor-acceptor ensemble 1/2, obtaining similar results. The 1:1 stoichiometry of 1/2 and 3/2 was also confirmed by mass spectrometry. The spectra recorded from a 1:1 mixture of the two components of each complex display peaks at m/z = 2618 and 3351, respectively.
43. Closer inspection of Figure 8 reveals that simultaneous with the quenching of the ZnPc 1 emission at 704 nm, a new lower-energy emission develops, which is centered at 702 nm.
44. However, given the margin of error, it was very difficult to analyze the decays of the 3/2 ensemble. Still a double-exponential fitting provides the best results.
45. Although the intra-ensemble transduction of the excited-state energy must occur in the singlet excited states, our picosecond analysis was unsuccessful to confirm this. Our failure is mainly due to the similar singlet excited-state features of the two phthalocyanine building blocks.
46. Our picosecond analysis was unsuccessful to resolve the transduction of energy.
47. Wei, X.; Yao, S.; Yin, G.; Suo, Z.; Xu, Z.; Wang, P.; Zhang, W.; Chen, P.; Zhang, Y.; Li, Z.; Niu, Y. Fullerene, nanotubes carbon nanostructures 2002, 10, 137.
48. García-Frutos, E. Ph.D. Thesis, Universidad Autónoma de Madrid, 2002.
49. Mckean, D. R.; Parrinello, G.; Renaldo, A. F.; Stille, J. K. J. Org. Chem. 1987, 52, 422.
50. Maya, E. M.; García, C.; García-Frutos, E. M.; Vázquez, P.; Torres, T. J. Org. Chem. 2000, 65, 2733.