Essential role of the ancillary ligand in the color tuning of iridium tetrazolate complexes

Inorganic Chemistry

Volumn 47, Issue 22, 2008, Pages 10509-10521

  Stagni, Stefano ^a   Colella, Silvia ^b,c   Palazzi, Antonio ^a   Valenti, Giovanni ^a   Zacchini, Stefano ^a   Paolucci, Francesco ^a   Marcaccio, Massimo ^a   Albuquerque, Rodrigo Q ^b   De Cola, Luisa ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c NATIONAL NANOTECHNOLOGY LABORATORY   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57149093216     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic801157k     Document Type: Article

References (82)

1. (a) Flamigni, L.; Barbieri, A.; Sabatini, C.; Ventura, B.; Barigelletti, F. Top. Curr. Chem. 2007, 281, 143, and references cited therein.
2. (b) See also: Dixon, I. M.; Collin, J.-P.; Sauvage, J.-P.; Flamigni, L.; Encinas, S.; Barigelletti, F. Chem. Soc. Rev. 2000, 29, 385.
3. (a) Holder, E.; Langeveld, B. M. W.; Schubert, U. S. Adv. Mater. 2005, 17, 1109, and references cited therein.
4. (b) Baldo, M. A.; Thompson, M. E.; Forrest, S. R. Nature 2000, 403, 750.
5. (c) Adachi, C.; Baldo, M. A.; Forrest, S. R.; Thompson, M. E. Appl. Phys. Lett. 2000, 77, 904.
6. (d) Adachi, C.; Baldo, M. A.; Thompson, M. E.; Forrest, S. R. J. Appl. Phys. 2001, 90, 5048.
7. (a) Chi, Y.; Chou, P.-T. Chem. Soc. Rev. 2007, 36, 1421, and references cited therein.
8. See also: (b) Mayo, E. I.; Kilsa, K.; Tirrell, T.; Djurovich, P. I.; Tamayo, A.; Thompson, M. E.; Lewis, N. S.; Gray, H. B. Photochem. Photobiol. Sci. 2006, 5, 871.
9. (a) Yu, M.-X.; Zhao, Q.; Shi, L.-X.; Li, F.-Y.; Zhou, Z.-G.; Yang, H.; Yia, T.; Huang, C.-H. Chem. Commun. 2008, 2115.
10. (b) Lo, K. K. W.; Lau, J. S. Y. Inorg. Chem. 2007, 46, 700.
11. (c) Lo, K. K. W.; Zhang, K. Y.; Chung, C. K.; Kwok, K. Y. Chem. - Eur. J. 2007, 13, 7110.
12. (d) Lo, K. K.W.; Chung, C. K.; Zhu, N. Chem. - Eur. J. 2006, 12, 1500, and references cited therein.
13. Evans, R. C.; Douglas, P.; Winscom, C. J. Coord. Chem. Rev. 2006, 250, 2093.
14. Campagna, S.; Puntoriero, F.; Nastasi, F.; Bergamini, G.; Balzani, V. Top. Curr. Chem. 2007, 280, 117, and references cited therein.
15. (a) For red-emitting species, see: Tsuboyama, A.; Iwawaki, H.; Furugori, M.; Mukaide, T.; Kamatani, J.; Igawa, S.; Moriyama, T.; Miura, S.; Takiguchi, T.; Okada, S.; Hoshino, M.; Ueno, K. J. Am. Chem. Soc. 2003, 125, 12971.
16. (b) Liang, B.; Jiang, C. Y.; Chen, Z.; Zhang, X. J.; Shi, H. H.; Cao, Y. J. Mater. Chem. 2006, 16, 1281-1286.
17. (c) Liu, Z. W.; Guan, M.; Bian, Z. Q.; Nie, D. B.; Gong, Z. L.; Li, Z. B.; Huang, C. H. Adv. Funct. Mater. 2006, 16, 1441.
18. (d) Song, Y.-H.; Yeh, S.-J.; Chen, C.-T.; Chi, Y.; Liu, C.-S.; Yu, J.-K.; Hu, Y.-H.; Chou, P.-T.; Peng, S.-M.; Lee, G.-H. Adv. Funct. Mater. 2004, 14, 1221, and references cited therein.
19. (a) For blue-emitting species, see: Chang, C.-F.; Cheng, Y.-M.; Chi, Y.; Chiu, Y.-C.; Lin, C.-C.; Lee, G.-H.; Chou, P.-T.; Chen, C.-C.; Chang, C.-H.; Wu, C.-C. Angew. Chem., Int. Ed. 2008, 47, 4542.
20. (b) Orselli, E.; Kottas, G. S.; Konradsson, A. E.; Coppo, P.; Fröhlich, R.; De Cola, L.; van Dijken, A.; Büchel, M.; Börner, H. Inorg. Chem. 2007, 46, 11082, and references cited therein.
21. See also: (c) Yang, C. H.; Cheng, Y. M.; Chi, Y.; Hsu, C. J.; Fang, F. C.; Wong, K. T.; Chou, P. T.; Chang, C. H.; Tsai, M. H.; Wu, C. C. Angew. Chem., Int. Ed. 2007, 46, 2418.
22. (d) Ragni, R.; Plummer, E. A.; Brunner, K.; Hofstraat, J. W.; Babudri, F.; Farinola, G. M.; Naso, F.; De Cola, L. J. Mater. Chem. 2006, 16, 1161.
23. (e) Yang, C. H.; Li, S. W.; Chi, Y.; Cheng, Y. M.; Yeh, Y. S.; Chou, P. T.; Lee, G. H.; Wang, C. H.; Shu, C. F. Inorg. Chem. 2005, 44, 7770.
24. (f) Coppo, P.; Plummer, E. A.; De Cola, L. Chem. Commun. 2004, 1774.
25. (g) Sajoto, T.; Djurovich, P. I.; Tamayo, A.; Yousufuddin, M.; Bau, R.; Thompson, M. E.; Holmes, R. J.; Forrest, S. R. Inorg. Chem. 2005, 44, 7992.
26. (h) Tamayo, A. B.; Alleyne, B. D.; Djurovich, P. I.; Lamansky, S.; Tsyba, I.; Ho, N. N.; Bau, R.; Thompson, M. E. J. Am. Chem. Soc. 2003, 125, 7377.
27. (a) Sun, Y. R.; Giebink, N. C.; Kanno, H.; Ma, B. W.; Thompson, M. E.; Forrest, S. R. Nature 2006, 440, 908, and references cited therein.
28. (b) Kanno, H.; Holmes, R. J.; Sun, Y.; Kena-Cohen, S.; Forrest, S. R. Adv. Mater. 2006, 18, 339.
29. (c) Coppo, P.; Duati, M.; Kozhevnikov, V. N.; Hofstraat, J. W.; De Cola, L. Angew. Chem., Int. Ed. 2005, 44, 1806.
30. (d) Gong, X.; Wang, S.; Moses, D.; Bazan, G. C.; Heeger, A. J. Adv. Mater. 2005, 17, 2053.
31. (e) D'Andrade, B. W.; Forrest, S. R. Adv. Mater. 2004, 16, 1585.
32. (a) Mehlstäubl, M.; Kottas, G. S.; Colella, S.; De Cola, L. Dalton Trans. 2008, 2385.
33. (b) Chen, H.-Y.; Yang, C.-H.; Chi, Y.; Cheng, Y.-M.; Yeh, Y.-S.; Chou, P.-T.; Hsieh, H.-Y.; Liu, C.-S.; Peng, S.-M.; Lee, G.-H. Can. J. Chem. 2006, 84, 309.
34. Montalti, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry; Taylor and Francis: Boca Raton, FL, 2006,
35. (a) Yersin, H. Top. Curr. Chem. 2004, 241, 1.
36. (b) Lamansky, S.; Djurovich, P.; Murphy, D.; Abdel-Razzaq, F.; Kwong, R.; Tsyba, I.; Bortz, M.; Mui, B.; Bau, R.; Thompson, M. E. Inorg. Chem. 2001, 40, 1704.
37. + species, see: Dragonetti, C.; Falciola, L.; Mussini, P.; Righetto, S.; Roberto, D.; Ugo, R.; Valore, A.; De Angelis, F.; Fantacci, S.; Sgamellotti, A.; Ramon, M.; Muccini, M. Inorg. Chem. 2007, 46, 8533.
38. (b) Nazeeruddin, Md. K.; Wegh, R. T.; Zhou, Z.; Klein, C.; Wang, Q.; De Angelis, F.; Fantacci, S.; Grätzel, M. Inorg. Chem. 2006, 45, 9245.
39. (c) Zhao, Q.; Liu, S.; Shi, M.; Wang, C.; Yu, M.; Li, L.; Li, F.; Yi, T.; Huang, C. Inorg. Chem. 2006, 45, 6152.
40. (d) Tamayo, A. B.; Garon, S.; Sajoto, T.; Djurovich, P. I.; Tsyba, I. M.; Bau, R.; Thompson, M. E. Inorg. Chem. 2005, 44, 8723.
41. (e) Nazeeruddin, Md. K.; Humphry-Baker, R.; Berner, D.; Rivier, S.; Zuppiroli, L.; Grätzel, M. J. Am. Chem. Soc. 2003, 125, 8790, and references cited therein.
42. (a) For an excellent overview of the various 2-pyridylazolates employed as ligands for phosphorescent species, see: Chou, P.-T.; Chi, Y. Chem. - Eur. J. 2007, 13, 380, and references cited therein.
43. See also: (b) Chang, C.-J.; Yang, C.-H.; Chen, K.; Chi, Y.; Shu, C.-F.; Ho, M.-L.; Yeh, Y.-S.; Chou, P.-T. Dalton Trans. 2007, 1881 and references cited therein.
44. (a) Wu, L.-L.; Yang, C.-H.; Sun, I.-W.; Chu, S.-Y.; Kao, P.-C.; Huang, H.-H. Organometallics 2007, 26, 2017.
45. (b) Yeh, S.-J.; Wu, M.-F.; Chen, C.-T.; Song, Y.-H.; Chi, Y.; Ho, M.-H.; Hsu, S.-F.; Chen, C. H. Adv. Mater. 2005, 17, 285.
46. (a) For polypyridylruthenium(II) tetrazolate complexes, see: Stagni, S.; Orselli, E.; Palazzi, A.; De Cola, L.; Zacchini, S.; Femoni, C.; Marcaccio, M.; Paolucci, F.; Zanarini, S. Inorg. Chem. 2007, 46, 9126.
47. (b) Stagni, S.; Palazzi, A.; Zacchini, S.; Ballarin, B.; Bruno, C.; Marcaccio, M.; Paolucci, F.; Monari, M.; Carano, M.; Bard, A. J. Inorg. Chem. 2006, 45, 695.
48. (c) Zanarini, S.; Bard, A. J.; Marcaccio, M.; Palazzi, A.; Paolucci, F.; Stagni, S. J. Phys. Chem. B 2006, 110, 22551.
49. (d) Duati, M.; Tasca, S.; Lynch, F. C.; Bohlen, H.; Vos, J. G.; Stagni, S.; Ward, M. D. Inorg. Chem. 2003, 42, 8377.
50. (e) Massi, M.; Cavallini, M.; Stagni, S.; Palazzi, A.; Biscarini, F. Mater. Sci. Eng. C 2003, 23, 923.
51. (a) For cyclopentadienyliron(II) tetrazolate complexes, see: Palazzi, A.; Stagni, S. J. Organomet. Chem. 2005, 690, 2052.
52. (b) Palazzi, A.; Stagni, S.; Monari, M.; Selva, S. J. Organomet. Chem. 2003, 669, 135.
53. (c) Palazzi, A.; Stagni, S.; Bordoni, S.; Monari, M.; Selva, S. Organometallics 2002, 21, 3774.
54. Neve, F.; La Deda, M.; Crispini, A.; Bellusei, A.; Puntoriero, F.; Campagna, S. Organometallics 2004, 23, 5856.
55. Torsion angles N(1)-C(1)-C(2)-N(5) are 3.0(9)°, -0.1(5)°, and 9(2)° and C(3)-C(2)-C(1)-N(4) are 4.1(12)°, 0.6(7)°, and 6(3)° for Ir(PyTz), Ir(PzTz), and Ir(BrPyTz), respectively.
56. (a) Benassi, R.; Bertarini, C.; Taddei, F. Chem. Phys. Lett. 1996, 257, 633.
57. (b) Prasad, M. A.; Sangaranarayanan, M. V. Chem. Phys. Lett. 2005, 414, 55.
58. (c) Antonello, S.; Maran, F. Chem. Soc. Rev. 2005, 34, 418.
59. (d) Costentin, C.; Robert, M.; Saveant, J.-M. Chem. Phys. 2006, 324, 40, and references cited therein.
60. Further electrochemical investigations are currently underway, and the results will be reported in a following paper.
61. Plummer, E. A.; Hofstraat, J. W.; De Cola, L. Dalton Trans. 2003, 2080.
62. Zeng, X. M.; Tavasli, M.; Perepichka, I. F.; Batsanov, A. S.; Bryce, M. R.; Chiang, C.-J.; Rothe, C.; Monkman, A. P. Chem. - Eur. J. 2008, 14, 933.
63. 3MLCT nature, as witnessed by the emission profiles reported in Figures S9 and S11 in the Supporting Information.
64. Sprouse, S.; King, K. A.; Spellane, P. J.; Watts, R. J. J. Am. Chem. Soc. 1984, 106, 6647.
65. Butler, R. N. Tetrazoles. In Comprehensive Heterocyclic Chemistry II; Storr, R. C., Ed.; Pergamon Press: Oxford, U.K., 1996; Vol. 4, pp 621-678, and references cited therein.
66. Wilker, W.; Leibfritz, D.; Kerssebaum, R.; Beimel, W. Magn. Reson. Chem. 1993, 31, 287.
67. Hurd, R. E. J. Magn. Reson. 1990, 87, 422.
68. (a) La Pensée, A. A.; Bickley, J.; Higgins, S. J.; Marcaccio, M.; Paolucci, F.; Roffia, S.; Charnock, J. M. J. Chem. Soc., Dalton Trans. 2002, 4095.
69. (b) Cecchet, F.; Gioacchini, A. M.; Marcaccio, M.; Paolucci, F.; Roffia, S.; Alebbi, M.; Bignozzi, C. A. J. Phys. Chem. B 2002, 106, 3926.
70. (a) Marcaccio, M.; Paolucci, F.; Paradisi, C.; Roffia, S.; Fontanesi, C.; Yellowlees, L. J.; Serroni, S.; Campagna, S.; Balzani, V. J. Am. Chem. Soc. 1999, 121, 10081.
71. (b) Marcaccio, M.; Paolucci, F.; Paradisi, C.; Carano, M.; Roffia, S.; Fontanesi, C.; Yellowlees, L. J.; Serroni, S.; Campagna, S.; Balzani, V. J. Electroanal. Chem. 2002, 532, 99.
72. Amatore, C.; Lefrou, C. J. Electroanal. Chem. 1992, 324, 33.
73. Antigona developed by Dr. Loïc Mortier, University of Bologna, Bologna, Italy, 1999.
74. Eaton, D. F. Pure Appl. Chem. 1988, 60, 1107.
75. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
76. Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958, 80, 3909.
77. Jo, Y. W.; Im, W. B.; Rhee, J. K.; Shim, M. J.; Kim, W. B.; Choi, E. C. Bioorg. Med. Chem. 2004, 12, 5909.
78. Kuroboshi, M.; Waki, Y.; Tanaka, H. J. Org. Chem. 2003, 68, 3938.
79. Sheldrick, G. M. SADABS, Program for empirical absorption correction; University of Göttingen: Göttingen, Germany, 1996.
80. Sheldrick, G. M. SHELX97, Program for crystal structure determination; University of Göttingen: Göttingen, Germany, 1997.
81. Sheldrick, G. M. CELL_NOW, Program for unit cell determination; University of Göttingen: Göttingen, Germany, 2005.
82. APEX2 User Manual; Bruker AXS Inc.: Madison, WI, 2005.