Control of photoinduced electron transfer in zinc phthalocyanine- perylenediimide dyad and triad by the magnesium ion

Journal of Physical Chemistry A

Volumn 112, Issue 43, 2008, Pages 10744-10752

  Fukuzumi, Shunichi ^a   Ohkubo, Kei ^a   Ortiz, Javier ^b   Gutiérrez, Ana M ^b   Fernández Lázaro, Fernando ^b   Sastre Santos, Ángela ^b  

^a OSAKA UNIVERSITY   (Japan)

^b MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; BINDING ENERGY; ELECTRON TRANSITIONS; EMISSION SPECTROSCOPY; EXCITED STATES; IONS; MAGNESIUM; METAL IONS; PHOTOEXCITATION; ZINC; ZINC COMPOUNDS;

ABSORPTION BANDS; CS STATES; ELECTRON OXIDATIONS; ELECTRON REDUCTIONS; ESR SPECTRUMS; FLUORESCENCE EMISSIONS; MAGNESIUM IONS; PERYLENEDIIMIDE; PHOTOINDUCED ELECTRON TRANSFERS; TIME-RESOLVED; TRANSIENT ABSORPTION SPECTRUMS; ZINC PHTHALOCYANINES;

MAGNESIUM PRINTING PLATES;

DRUG DERIVATIVE; IMIDE; INDOLE DERIVATIVE; ION; MAGNESIUM; ORGANOMETALLIC COMPOUND; PERYLENE; PERYLENEDIIMIDE; ZN(II) PHTHALOCYANINE; ZN(II)-PHTHALOCYANINE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; ELECTRON; LASER; PHOTOCHEMISTRY; PHOTOLYSIS; SYNTHESIS; TIME;

COMPUTER SIMULATION; ELECTRONS; IMIDES; INDOLES; IONS; LASERS; MAGNESIUM; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PERYLENE; PHOTOCHEMISTRY; PHOTOLYSIS; TIME FACTORS;

EID: 56049126474     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp805464e     Document Type: Article

References (78)

1. (a) Gust, D.; Moore, T. A. In The Porphyrin Handbook; Kadish, K. M., SmithK. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 8, pp 153-190.
2. (b) Gust, D.; Moore, T. A.; Moore, A. L. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 3, pp 272-336.
3. (c) Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res. 2001, 34, 40.
4. (a) Wasielewski, M. R. In Photoinduced Electron Transfer, Fox, M. A., Chanon, M., Eds.; Elsevier: Amsterdam, 1988; Part A, pp161-206.
5. (b) Wasielewski, M. R. Chem. Rev. 1992, 92, 435.
6. (a) Guldi, D. M. Chem. Soc. Rev. 2002, 31, 22-36.
7. (b) Guldi, D. M. Chem. Commun. 2000, 321.
8. (a) Paddon-Row, M. N. Acc. Chem. Res. 1994, 27, 18.
9. (b) Jordan, K. D.; Paddon-Row, M. N. Chem. Rev. 1992, 92, 395.
10. Blanco, M.-J.; Consuelo Jiménez, M.; Chambron, J.-C.; Heitz, V.; Linke, M.; Sauvage, J.-P. Chem. Soc. Rev. 1999, 28, 293.
11. (a) Fukuzumi, S.; Guldi, D. M. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 270-337.
12. (b) Fukuzumi, S. Org. Biomol. Chem. 2003, 1, 609.
13. (a) Imahori, H.; Tamaki, K.; Guldi, D. M.; Luo, C.; Fujitsuka, M.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 2607.
14. (b) Imahori, H.; Guldi, D. M.; Tamaki, K.; Yoshida, Y.; Luo, C.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6617.
15. (c) Imahori, H.; Sekiguchi, Y.; Kashiwagi, Y.; Sato, T.; Araki, Y.; Ito, O.; Yamada, H.; Fukuzumi, S. Chem.-Eur. J. 2004, 10, 3184.
16. (a) Imahori, H.; Tamaki, K.; Araki, Y.; Sekiguchi, Y.; Ito, O.; Sakata, Y.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 5165.
17. (b) Guldi, D. M.; Imahori, H.; Tamaki, K.; Kashiwagi, Y.; Yamada, H.; Sakata, Y.; Fukuzumi, S. J. Phys. Chem. A 2004, 108, 541.
18. (a) Würthner, F. Chem. Commun. 2004, 1564.
19. (b) Langhals, H. Helv. Chim. Acta 2005, 88, 1309.
20. (c) Wasielewski, M. R. J. Org. Chem. 2006, 71, 5051.
21. (a)Würthner, F. Angew. Chem. 2001, 113, 1069;
22. Angew. Chem. Int. Ed. 2001, 40, 1037.
23. (b) Tan, L.; Curtis, M. D.; Francis, A. H. Chem. Mater. 2004, 16, 2134.
24. (c) Tatemichi, S.; Ichikawa, M.; Koyama, T.; Taniguchi, Y. Appl. Phys. Lett. 2006, 89, 112108.
25. (a) Phthalocyanines: Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH: Weinheim, 1989, 1993, 1996; Vols. 1-4.
26. (b) Hanack, M.; Heckmann, H.; Polley R. In Methods in Organic Chemistry (Houben-Weyl); Schumann, E., Ed.; Thieme: Stuttgart, 1998; Vol. E 9d, p 717.
27. (c) 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, 2003.
28. de la Torre, G.; Claessens, C. G.; Torres, T. Chem. Commun. 2007, 2000.
29. (a) Miller, M. A.; Lammi, R. K.; Prathapan, S.; Holten, D.; Lindsey, J. S. J. Org. Chem. 2000, 65, 6634.
30. (b) Li, X.; Sinks, L. E.; Rybtchinski, B.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 10810.
31. (a) Rodríguez-Morgade, M. S.; Torres, T.; Atienza-Castellanos, C.; Guldi, D. J. Am. Chem. Soc. 2006, 128, 15145.
32. (b) Jiménez, A. J.; Spänig, F.; Rodríguez-Morgade, M. S.; Ohkubo, K.; Fukuzumi, S.; Guldi, D. M.; Torres, T. Org. Lett. 2007, 9, 2481.
33. (a) Liu, M. O.; Tai, C.-H.; Hu, A. T. J. Photochem. Photobiol. A: Chem. 2004, 165, 193.
34. (b) Gao, B.; Li, Y.; Su, J.; Tian, H. Supramol. Chem. 2007, 19, 207.
35. (c) Chen, Y.; Lin, Y.; EI-Khouly, M. E.; Zhuang, X.; Araki, Y.; Ito, O.; Zhang, W. J. Phys. Chem. C 2007, 111, 16096.
36. (a) You, C.-C.; Würthner, F. Org. Lett. 2004, 6, 2401.
37. (b) Kirmaier, C.; Yang, S. I.; Prathapan, S.; Miller, M. A.; Diers, J. R.; Bacian, D. F.; Lindsey, J. S.; Holten, D. Res. Chem. Intermed. 2002, 28, 719.
38. (c) Yang, S. I.; Lammi, R. K.; Prathapan, S.; Miller, M. A.; Seth, J.; Diers, J. R.; Bacian, D. F.; Lindsey, J. S.; Holten, D. J. Mater. Chem. 2001, 11, 2420.
39. (d) Gosztola, D.; Niemczyk, M. P.; Wasielewski, M. R. J. Am. Chem. Soc. 1998, 120, 5118-5119.
40. (e) Kelley, R. F.; Suk Shin, W.; Rybtchinski, B.; Sinks, L. E.; Wasielewski, M. R. J. Am. Chem. Soc. 2007, 129, 3173.
41. (a) Fukuzumi, S. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, 2001; Vol. 4, pp 3-67.
42. (b) Fukuzumi, S.; Itoh, S. In Advances in Photochemistry; Neckers, D. C., Volman, D. H. von Bünau, G., Eds.; Wiley: New York, 1998; Vol. 25, pp 107-172..
43. (a) Fukuzumi, S. Bull. Chem. Soc. Jpn. 1997, 70, 1
44. (b) Fukuzumi, S. Org. Biomol. Chem. 2003, 1, 609.
45. (a) Fukuzumi, S.; Koumitsu, S.; Hironaka, K.; Tanaka, T. J. Am. Chem. Soc. 1987, 109, 305.
46. (b) Fukuzumi, S.; Nishizawa, N.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1985, 371-378.
47. (a) Fukuzumi, S.; Okamoto, T.; Otera, J. J. Am. Chem. Soc. 1994, 116, 5503.
48. (b) Fukuzumi, S.; Satoh, N.; Okamoto, T.; Yasui, K.; Suenobu, T.; Seko, Y.; Fujitsuka, M.; Ito, O. J. Am. Chem. Soc. 2001, 123, 7756.
49. (c) Fukuzumi, S.; Mon, H.; Imahori, H.; Suenobu, T.; Araki, Y.; Ito, O.; Kadish, K. M. J. Am. Chem. Soc. 2001, 123, 12458.
50. (d) Fukuzumi, S.; Fujii, Y.; Suenobu, T. J. Am. Chem. Soc. 2001, 123, 10191.
51. (a) Fukuzumi, S.; Ohkubo, K.; Okamoto, T. J. Am. Chem. Soc. 2002, 124, 14147.
52. (b) Fukuzumi, S.; Inada, O.; Satoh, N.; Suenobu, T.; Imahori, H. J. Am. Chem. Soc. 2002, 124, 9181.
53. (c) Fukuzumi, S.; Yuasa, J.; Suenobu, T. J. Am. Chem. Soc. 2002, 124, 12566.
54. (a) Fukuzumi, S.; Okamoto, K.; Imahori, H. Angew. Chem., Int. Ed. 2002, 41, 620.
55. (b) Fukuzumi, S.; Okamoto, K.; Yoshida, Y.; Imahori, H.; Araki, Y.; Ito, O. J. Am. Chem. Soc. 2003, 125, 1007.
56. (a) Fukuzumi, S.; Ohkubo, K Chem. Eur. J. 2000, 6, 4532.
57. (b) Fukuzumi, S.; Ohkubo, K. J. Am. Chem. Soc. 2002, 124, 10270.
58. Fukuzumi, S.; Ohkubo, K.; Ortiz, J.; Gutiérrez, A. M.; Fernández-Lázaro, F.; Sastre-Santos, Á. Chem. Commun. 2005, 3814.
59. Gaspard, S.; Maillard, P. Tetrahedron 1987, 43, 1083.
60. Demming, S.; Langhals, H. Chem. Ber. 1988, 121, 225.
61. Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Nonaqueous Systems; Marcel Dekker: New York, 1990.
62. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
63. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
64. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
65. Yilmaz, M. D.; Bozdemir, O. A.; Akkaya, E. U. Org. Lett. 2006, 8, 2871.
66. The triplet energy of zinc phthalocyanine has been reported:(a) Harriman, A.; Porter, G.; Richoux, M-C. J. Chem. Soc., Faraday Trans. 1971, 55, 4131.
67. (b) Vincett, P. S.; Voight, E. M.; Rjeckhoff, K. E. J. Chem. Phys. 1971, 55, 4130.
68. (c) Herkstroeter, W. G.; Merkel, P. B. J. Photochem. 1981, 16, 331.
69. The triplet energy of perylenediimide derivatives has been reported Ford, W. E.; Kamat, P. V. J. Phys. Chem. 1987, 91, 6373.
70. Gosztola, D.; Niemczyk, M. P.; Svec, W.; Lukas, A. S.; Wasielweski, M. R. J. Phys. Chem. A 2000, 104, 6545.
71. Dance, Z. E. X.; Mi, Q.; McCamant, D. W.; Ahrens, M. J.; Ratner, M. A.; Wasielewski, M. R. J. Phys. Chem. B 2006, 110, 25163.
72. 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.
73. Photoexcitation of zinc porphyrin-naphthalenediimide also affords the CS state, the lifetime of which can be altered by the coordination of metal ions to the naphthalenediimide moiety; see: Okamoto, K.; Mon, Y.; Yamada, H.; Imahori. H.; Fukuzumi. S. Chem.-Eur. J. 2004, 10, 474.
74. Fukuzumi, S.; Suenobu, T.; Patz, M.; Hirasaka, T.; Itoh, S.; Fujitsuka, M.; ho, O. J. Am. Chem. Soc. 1998, 120, 8060.
75. 2+; see: Fukuzumi, S.; Ohkubo, K.; Okamoto, T. J. Am. Chem. Soc. 2002, 124, 14147.
76. 2+ nucleus.
77. (a) Fukuzumi, S.; Ohkubo, K.; Imahori, H.; Shao, J.; Ou, Z.; Zheng, G.; Chen, Y.; Pandey, R. K.; Fujitsuka, M.; Ito, O.; Kadish, K. M. J. Am. Chem. Soc. 2001, 123, 10676.
78. (b) Kryatov, S. V.; Rybak-Akimova, E. V.; Schindler, S. Chem. Rev. 2005, 105, 2175.