Control over charge separation in phthalocyanine-anthraquinone conjugates as a function of the aggregation status

Journal of the American Chemical Society

Volumn 128, Issue 39, 2006, Pages 12674-12684

  Gouloumis, Andreas ^a,b   González Rodríguez, David ^a   Vázquez, Purificación ^a   Torres, Tomás ^a   Liu, Shenggao ^c,f   Echegoyen, Luis ^c   Ramey, Jeff ^e   Hug, Gordon L ^d   Guldi, Dirk M ^e  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^c CLEMSON UNIVERSITY   (United States)

^d UNIVERSITY OF NOTRE DAME   (United States)

^e UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^f CHEVRON ENERGY TECHNOLOGY COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AQ ACCEPTORS; ELECTRONIC COMMUNICATIONS; INTRAMOLECULAR LEVELS; PLANAR SYSTEMS;

CHARGE TRANSFER; ELECTRONIC PROPERTIES; MOLECULES; OLIGOMERS; ORGANIC SOLVENTS; REACTION KINETICS; TOPOLOGY;

AROMATIC COMPOUNDS;

ANTHRAQUINONE; AROMATIC COMPOUND; OLIGOMER; PHTHALOCYANINE; SOLVENT; VINYL DERIVATIVE; ZINC;

ARTICLE; CONJUGATE; CONJUGATION; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ISOMER; MOLECULAR INTERACTION; PHOTOCHEMISTRY; SEPARATION TECHNIQUE; TECHNIQUE;

EID: 33749542310     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055344+     Document Type: Article

References (100)

1. (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Ellis Horwood: Chichester, U.K., 1991; pp 161-196, 355-394.
2. (b) Electron Transfer in Chemistry, Vol. I-V; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001.
3. For some representative examples, see: (a) Imahori, H.; Yamada, H.; Guldi, D. M.; Endo, Y.; Shimomura, A.; Kundu, S.; Yamada, K.; Okada, T.; Sakata, Y.; Fukuzumi, S. Angew. Chem., Int. Ed. 2002, 41, 2344-2347.
4. (b) Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395-410.
5. (c) Lewis, F. D.; Letsinger, R. L.; Wasielewski, M. R. Acc. Chem. Res. 2001, 34, 159-170.
6. (d) Smitha, M. A.; Prasad, E.; Gopidas, K. R. J. Am. Chem. Soc. 2001, 123, 1159-1165.
7. (e) Masahiko, S.; Satoshi, H.; Kusano, H.; Kuragaki, M.; Makino, M.; Sasaki, H.; Smith, T. A.; Ghiggino, K. P. J. Phys. Chem. B 2001, 105, 10407-10415.
8. (f) 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, 9166-9167.
9. (g) Guldi, D. M.; Hirsch, A.; Scheloske, M.; Dietel, E.; Troisi, A.; Zerbetto, F.; Prato, M. Chem.-Eur. J. 2003, 9, 4968-4979.
10. (h) Guldi, D. M.; Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc. 1997, 119, 8363.
11. (i) Gust, D.; Moore, T. A.; Moore, A. L.; Devadoss, C.; Liddell, P. A.; Hermant, R.; Nieman, R. A.; Demanche, L. J.; DeGraziano, J. M.; Gouni, I. J. Am. Chem. Soc. 1992, 114, 3590-3603.
12. (j) Imahori, H.; Hagiwara, K.; Aoki, M.; Akiyama, T.; Taniguchi, S.; Okada, T.; Shirakawa, M.; Sakata, Y. J. Am. Chem. Soc. 1996, 118, 11771-11782.
13. (k) Tsue, H.; Imahori, H.; Kaneda, T.; Tanaka, Y.; Okada, T.; Tamaki, K.; Sakata, Y. J. Am. Chem. Soc. 2000, 122, 2279-2288.
14. Kilsa, K.; Kajanus, J.; Macpherson, A. N.; Martensson, J.; Albinsson, B. J. Am. Chem. Soc. 2001, 123, 3069-3080.
15. Lokan, N. R.; Paddon-Row, M. N.; Koeberg, M.; Verhoeven, J. W. J. Am. Chem. Soc. 2000, 122, 5075-5081.
16. (n) Imahori, H.; El-Khouly, M. E.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2001, 105, 325-332.
17. (o) Fujitsuka, M.; Tsuboya, N.; Hamasaki, R.; Ito, M.; Onodera, S.; Ito, O.; Yamamoto, Y. J. Phys. Chem. A 2003, 107, 1452-1458.
18. (a) Brabec, C.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15-26.
19. (b) Winder, C.; Sariciftci, N. S. J. Mater. Chem. 2004, 14, 1077-1086.
20. (a) Eckert, J. F.; Nicoud, J. F.; Nierengarten, J. F.; Liu, S. G.; Echegoyen, L.; Barigelletti, F.; Armaroli, N.; Ouali, L.; Krasnikov, V.; Hadziioannou, G. J. Am. Chem. Soc. 2000, 122, 7467-7479.
21. (b) Peeters, E.; Hal, P. A. V.; Knol, J.; Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C.; Janssen, R. A. J. J. Phys. Chem. B 2000, 104, 10174-10190.
22. (c) Wang, L. H.; Chen, Z. K.; Xiao, Y.; Kang, E. T.; Huang, W. Macromol. Rapid Commun. 2000, 21, 897-900.
23. (d) El-ghayoury, A.; Schenning, A. P. H. J.; van Hal, P. A.; van Duren, J. K. J.; Janssen, R. A. J. Angew. Chem., Int. Ed. 2001, 40, 3660-3663.
24. (e) Pourtois, G.; Beljonne, D.; Cornil, J.; Ratner, M. A.; Brédas, J. L. J. Am. Chem. Soc. 2002, 124, 4436-4447.
25. (f) Cravino, A.; Saricifti, N. S. J. Mater. Chem. 2002, 12, 1931-1943.
26. (a) Würthner, F.; Thalacker, C.; Sautter, A. Adv. Mater. 1999, 11, 754-758.
27. (b) El-ghayoury, A.; Peeters, E.; Schenning, A. P. H. J.; Meijer, E. W. Chem. Commun. 2000, 1969-1970.
28. (c) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; Mackenzie, J. D. Science 2001, 293, 1119-1122.
29. (d) Syamakumari, A.; Schenning, A. P. H. J.; Meijer, E. W. Chem-Eur. J. 2002. 8, 3353-3361.
30. (e) Samori, P.; Yin, X.; Tchebotareva, N.; Wang, Z.; Pakula, T.; Jäckel, F.; Watson, M. D.; Venturini, A.; Müllen, K.; Rabe, J. P. J. Am. Chem. Soc. 2004, 126, 3567-3575.
31. (a) Giaimo, J. M.; Gusev, A. V.; Wasielewski, M. R. J. Am. Chem. Soc. 2002, 124, 8530-8531.
32. (b) van der Boom, T.; Hayes, R. T.; Zhao, Y.; Bushard, P. J.; Weiss, E. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2002, 124, 9582-9590.
33. (c) Rybtchinski, B.; Sinks, L. E.; Wasielewski, M. R. J. Phys. Chem. A 2004, 108, 7497-7505.
34. (d) Ahrens, M. J.; Sinks, L. E.; Rybtchinski, B.; Liu, W.; Jones, B. A.; Giaimo, J. M.; Gusev, A. V.; Goshe, A. J.; Tiede, D. M.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 8284-8294.
35. (e) Marcos Ramos, A.; Meskers, S. C. J.; Beckers, E. H. A.; Prince, R. B.; Brunsveld, L.; Janssen, R. A. J. J. Am. Chem. Soc. 2004, 126, 9630-9644.
36. (f) Würthner, F.; Chen, Z.; Hoeben, F. J. M.; Osswald, P.; You, C.-C.; Jonkheijm, P.; Herrikhuyzen, J. V.; Schenning, A. P. H. J.; van der School, P. P. A. M.; Meijer, E. W.; Beckers, E. H. A.; Meskers, S. C. J.; Janssen, R. A. J. J. Am. Chem. Soc. 2004, 126, 10611-10618.
37. (g) Li, X.; Sinks, L. E.; Rybtchinski, B.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 10810-10811.
38. (h) Rybtchinski, B.; Sinks, L. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 12268-12269.
39. (i) Beckers, E. H. A.; Meskers, S. C. J.; Schenning, A. P. H. J.; Chen, Z.; Würthner, F.; Marsal, P.; Beljonne, D.; Cornil, J.; Janssen, R. A. J. J. Am. Chem. Soc. 2006, 128, 649-657.
40. (a) de la Torre, G.; Vázquez, P.; Agulló-López, F.; Torres, T. J. Mater. Chem. 1998, 8, 1671-1683.
41. (b) del Rey, B.; Keller, U.; Torres, T.; Rojo, G.; Agulló- López, F.; Nonell, S.; Marti, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1998, 120, 12808-12817.
42. (c) Claessens, C. G.; González-Rodríguez, D.; Torres, T. Chem. Rev. 2002, 102, 835-853.
43. (d) The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guillard, R., Eds.; Academic Press: San Diego, CA, 2003; Vols. 15-20.
44. (e) de la Torre, G.; Vázquez, P.; Agulló-López, F.; Torres, T. Chem. Rev. 2004, 104, 3723-3750.
45. (f) González-Rodríguez, D.; Torres, T.; Herranz, M. A.; Rivera, J.; Echegoyen, L.; Guldi, D. M. J. Am. Chem. Soc. 2004, 126, 6301-6313.
46. (g) Torres, T. Angew. Chem., Int. Ed. 2006, 45, 2834-2837;
47. Angew. Chem. 2006, 118, 2900-2903.
48. (a) He, J.; Benkö, G.; Korodi, F.; Polívka, T.; Lomoth, R.; Akermark, B.; Sun, L.; Hagfeldt, A.; Sundström, V. J. Am. Chem. Soc. 2002, 124, 4922.
49. (b) Loi, M. A.; Denk, P.; Hoppe, H.; Neugebauer, H.; Winder, C.; Meissner, D.; Brabec, C. J.; Sariciftci, N. S.; Gouloumis, A.; Vázquez, P.; Torres, T. J. Mater. Chem. 2003, 13, 700-704.
50. (c) Loi, M. A.; Denk, P.; Hoppe, H.; Neugebauer, H.; Meissner, D.; Winder, C.; Brabec, C. J.; Sariciftci, N. S.; Gouloumis, A.; Vázquez, P.; Torres, T. Synth. Met. 2003, 137, 1491-1492.
51. González, A.; Vázquez, P.; Torres, T.; Guldi, D. M. J. Org. Chem. 2003, 68, 8635-8642.
52. Farren, C.; Christensen, C. A.; FitzGerald, S.; Bryce, M. R.; Beeby, A. J. Org. Chem. 2002, 67, 9130-9139.
53. (a) Gouloumis, A.; Liu, S.-G.; Sastre, A.; Vázquez, P.; Echegoyen, L.; Torres, T. Chem.-Eur. J. 2000, 6, 3600-3607.
54. (b) González-Rodríguez, D.; Torres, T. In The Exciting World of Nanocages and Nanotubes: Kamat, P., Guldi, D. M., Kadish, K., Eds.; Proceeding of the Electrochemical Society, Fullerenes; ECS: Pennington, NJ, 2002: Vol. 12, pp 195-210.
55. (c) Guldi, D. M.; Zilbermann, I.; Gouloumis, A.; Vázquez, P.; Torres, T. J. Phys. Chem. B 2004, 108, 18485-18494.
56. (d) Guldi, D. M.; Gouloumis, A.; Vázquez, P.; Torres, T.; Georgakilas, V.; Prato, M. J. Am. Chem. Soc. 2005, 127, 5811-5813.
57. (e) de la Escosura, A.; Martínez-Díaz, M. V.; Guldi, D. M.; Torres, T. J. Am. Chem. Soc. 2006, 128, 4112-4118.
58. (a) Ambroise, A.; Wagner, R. W.; Rao, P. D.; Riggs, J. A.; Hascoat, P.; Diers, J. R.; Seth, J.; Lammi, R. K.; Bocian, D. F.; Holten, D.; Lindsey, J. S. Chem. Mater. 2001, 13, 1023-1034.
59. (b) Tomé, J. P. C.; Pereira, A. M. V. M.; Alonso, C. M. A.; Neves, M. G. P. M. S.; Tomé, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Martínez-Díaz, M. V.; Torres, T.; Guldi, D. M.; Rahman, G. M. A.; Ramey, J. Eur. J. Org. Chem. 2006, 257-267.
60. (a) González, A.; Vázquez, P.; Torres, T. Tetrahedron Lett. 1999, 40, 3263-3266.
61. (b) González, A.; Claessens, C. G.; Martin, G.; Ledoux, I.; Vázquez, P.; Zyss, J.; Agulló-López, F.; Torres, T. Synth. Met. 2003, 137, 1487-1488.
62. (a) Wasielewski, M. R. Chem. Rev. 1992, 34, 435-461.
63. (b) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 1993, 26, 198-205.
64. (c) Kurreck, H.; Huber, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 849-866.
65. (d) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40-48.
66. (e) Huber, M. Eur. J. Org. Chem. 2001, 23, 4379-4389.
67. (a) Li, L.; Shen, S.; Yu, Q.; Zhou, Q.; Xu, H. J. Chem. Soc., Chem. Commun. 1991, 619-620.
68. (b) Kobayashi, N.; Ohya, T.; Sato, M.; Nakajima, S. Inorg. Chem. 1993, 32, 1803-1808.
69. (c) Li, X.; Ng, D. K. P. Tetrahedron Lett. 2001, 42, 305-309.
70. (d) Gouloumis, A.; Liu, S.-G.; Vázquez, P.; Echegoyen, L.; Torres, T. Chem. Commun. 2001, 399-400.
71. Some excited-state properties of cofacial bisporphyrins have been studied: (a) Bolze, F.; Gros, C. P.; Harvey, P. D.; Guilard, R. J. Porphyrins Phthalocyanines 2001, 5, 569-574.
72. (b) Loh, Z.-H.; Miller, S. E.; Chang, C. J.; Carpenter, S. D.; Nocera, D. G. J. Phys. Chem. A 2002, 106, 11700-11708.
73. Similar 1,8-naphthalene-or 1,8-anthracene-linked bisphthalocyanines have been reported: (a) Leznoff, C. C.; Lam, H.; Nevin, W. A.; Kobayashi, N.; Janda, P.; Lever, A. B. P. Angew. Chem., Int. Engl. 1987, 26, 1021-1023.
74. (b) Lam, H.; Marcuccio, S. M.; Svirskaya, P. I.; Greenberg, S.; Lever, A. B. P.; Leznoff, C. C.; Cerny, R. L. Can. J. Chem. 1989, 67, 1087-1097.
75. (c) Kobayashi, N.; Yanagisawa, Y.; Osa, T.; Lam, H.; Leznoff, C. C. Anal. Chem. 1990, 6, 813-817.
76. (d) Kobayashi, N.; Lam, H.; Nevin, W. A.; Janda, P.; Leznoff, C. C.; Lever, A. B. P. Inorg. Chem. 1990, 29, 3415-3425.
77. Compound 2 was used as a statistical mixture of regioisomers that could not be separated by chromatography. See: Gürlach, B.; Dachtler, M.; Glaser, T.; Albert, K.; Hanack, M. Chem.-Eur. J. 2001, 29, 2459-2465.
78. (a) House, H.; Koepsell, D.; Campbell, W. J. Org. Chem. 1972, 37, 1003-1011.
79. (b) Kendall, J. K.; Shechter, H. J. Org. Chem. 2001, 66, 6643-6649.
80. For other methods of preparation, see: (a) Manecke, G.; Kretzschmar, H. J. Macromol. Chem. 1973, 169, 15-35.
81. (b) Tamayo, N.; Echavarren, A. M.; Paredes, M. C.; Fariña, F.; Noheda, P. Tetrahedron Lett. 1990, 36, 5189-5192.
82. For other methods of preparation, see: Murty, K. V. S. N.; Vasella, A. Helv. Chim. Acta 2001, 84, 939-963.
83. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 505-519.
84. Sonoghasira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 21, 4467-4470.
85. Snow, A. W. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guillard, R., Eds.; Academic Press: San Diego, CA. 2003; Vol. 17, pp 129-176.
86. In the case of compound 1c the maximum of the dimer band overlaps the red edge of the monomer absorption band (see Figures S9 and S10).
87. (a) Katayose, M.; Tai, S.; Kamijima, K.; Hagiwara, H.; Hayashi, N. J. Chem. Soc., Perkin Trans. 2 1992, 403-409.
88. (b) Kroon, J. M.; Koehorst, R. B. M.; van Dijk, M.; Sanders, G. M.; Sudhölter, E. J. R. J. Mater. Chem. 1997, 7, 615-624.
89. (a) McRae, E. G.; Kasha, M. J. Chem. Phys. 1958, 28, 721.
90. (b) Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure Appl. Chem. 1965, 11, 371.
91. -3 M) are too high to observe defined signals of the aromatic protons and, in the best cases, only broad signals from the protons of the tert-butyl groups were detected.
92. 4. See: Fernandez, D. A.; Awruch, J.; Dicelio, L. E. J. Photochem. Photobiol. 1996, 63, 784-792.
93. (a) Yoon, M.; Cheon, Y.; Kim, D. Photochem. Photobiol. 1993, 58, 31.
94. (b) Isago, H. Chem. Commun. 2003, 1864-1865.
95. However, no hints of intermolecular interactions between 2 and AQ were found in UV-vis titration experiments.
96. 2 ≈ 1) by a monoexponential decay function that yields lifetimes of 3.5 ± 0.5 ns (1a), 3.1 ± 0.2 ns (1b), and 2.9 ± 0.5 ns (1c). The authors would like to point out that, in the experiments in benzonitrile, much lower signal intensities (with respect to those in THF) were noted. No traces of Pc 2 contamination were found in the samples of 1a-c.
97. Belletête, M.; Bouchard, J.; Leclerc, M.; Durocher, G. Macromolecules 2005, 38, 880-887.
98. This maximum was determined in our previous work with picosecond resolved transient absorption measurements.
99. McCafferty, D. G.; Friesen, D. A.; Danielson, E.; Wall, C. G.; Saderholm, M. J.; Erickson, B. W.; Meyer. T. J. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8200-8204.
100. To confirm the intramolecular charge recombination dynamics we probed 1a-c at different laser powers and different concentrations. Regardless of the experimental conditions, the best fits were obtained by applying unimolecular decay functions that gave rise to the same charge recombination rate constants.