Cyclometalated platinum(II) complexes of pyrazole-based, N∧C∧N-coordinating, terdentate ligands: The contrasting influence of pyrazolyl and pyridyl rings on luminescence

Inorganic Chemistry

Volumn 47, Issue 23, 2008, Pages 11129-11142

  Develay, Stéphanie ^a   Blackburn, Octavia ^a   Thompson, Amber L ^a   Williams, J A Gareth ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57949086580     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic8014157     Document Type: Article

References (82)

1. For recent reviews, see for example: (a) McMillin, D. R.; Moore, J. J. Coord. Chem. Rev. 2002, 229, 113.
2. (b) Lai, S. W.; Che, C. M. Top. Curr. Chem. 2004, 241, 27.
3. (c) Ma, B.; Djurovich, P.; Thompson, M. E. Coord. Chem. Rev. 2005, 249, 1501.
4. (d) Castellano, F. N.; Pomestchenko, I. E.; Shikhova, E.; Hua, F.; Muro, M. L.; Rajapakse, N. Coord. Chem. Rev., 2006, 250, 1819.
5. (e) Wong, K. M. C.; Yam, V. W. W. Coord. Chem. Rev. 2007, 251, 2477.
6. (f) Williams, J. A. G. Top. Curr. Chem. 2007, 281, 205.
7. Barigelletti, F.; Sandrini, D.; Maestri, M.; Balzani, V.; von Zelewsky, A.; Chasot, L.; Jolliet, P.; Maeder, U. Inorg. Chem. 1988, 27, 3644.
8. (a) Chan, C.-W.; Cheng, L.-K.; Che, C.-M. Coord. Chem. Rev. 1994, 132, 87.
9. (b) Hissler, M.; Connick, W. B.; Geiger, D. K.; McGarrah, J. E.; Lipa, D.; Lachicotte, R. J.; Eisenberg, R. Inorg. Chem. 2000, 39, 447.
10. (c) Whittle, C. E.; Weinstein, J. A.; George, M. W.; Schanze, K. S. Inorg. Chem. 2001, 40, 4053.
11. (d) Yam, V. W. W.; Wong, K. M. C. Top. Curr. Chem. 2005, 257, 1.
12. (e) Rachford, A. A.; Goeb, S.; Ziessel, R.; Castellano, F. N. Inorg. Chem. 2008, 47, 4348.
13. (f) Lanoë, P.-H.; Fillaut, J.-L.; Toupet, L.; Williams, J. A. G.; Le Bozec, H.; Guerchais, V., Chem. Commun. [Online early access]. DOI: 10.1039/b806935b. Published Online: 2008; in press.
14. (a) Kvam, P.-I.; Puzyk, M. V.; Balashev, K. P.; Songstad, J. Acta Chem. Scand. 1995, 49, 335.
15. (b) Mdleleni, M. M.; Bridgewater, J. S.; Watts, R. J.; Ford, P. C. Inorg. Chem. 1995, 34, 2334.
16. (c) Brooks, J.; Babayan, Y.; Lamansky, S.; Djurovich, P. I.; Tsyba, I.; Bau, R.; Thompson, M. E. Inorg. Chem. 2002, 41, 3055.
17. (d) Yin, B.; Niemeyer, F.; Williams, J. A. G.; Jiang, J.; Boucekkine, A.; Toupet, L.; Le Bozec, H.; Guerchais, V. Inorg. Chem. 2006, 45, 8584.
18. (a) Cheung, T.-C.; Cheung, K.-K.; Peng, S.-M.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1996, 1645.
19. (b) Neve, F.; Crispini, A.; Campagna, S. Inorg. Chem. 1997, 36, 6150.
20. (c) Lai, S.-W.; Chan, M.C.-W.; Cheung, T.-C.; Peng, S.-M.; Che, C.-M. Inorg. Chem. 1999, 38, 4046.
21. (d) Wong, K.-H.; Chan, M.C.-W.; Che, C.-M. Chem. - Eur. J. 1999, 5, 2845.
22. (e) Ma, D.-L.; Che, C.-M. Chem. - Eur. J. 2003, 9, 6133.
23. For a review, see: (a) Chakraborty, S.; Wadas, T. J.; Hester, H.; Schmehl, R.; Eisenberg, R. Inorg. Chem. 2005, 44, 6865.
24. For example: (a) Adamovich, V.; Brooks, J.; Tamayo, A.; Alexander, A. M.; Djurovieh, P. I.; D'Andrade, B. W.; Adachi, C.; Forrest, S. R.; Thompson, M. E. New J. Chem. 2002, 26, 1171.
25. (b) Lu, W.; Mi, B.-X.; Chan, M.C.-W.; Hui, Z.; Che, C.-M.; Zhu, N.; Lee, S.-T. J. Am. Chem. Soc. 2004, 126, 4958.
26. (c) Cocchi, M.; Fattori, V.; Virgili, D.; Sabatini, S.; Di Marco, P.; Maestri, M.; Kalinowski, J. Appl. Phys. Lett. 2004, 84, 1052.
27. (d) He, Z.; Wong, W.-Y.; Yu, X.; Kwok, H.-S.; Lin, Z. Inorg. Chem. 2006, 45, 10922.
28. For recent reviews of Pt complexes applied to OLEDs, see: (a) Xiang, H.-F.; Lai, S.-W.; Lai, P. T.; Che, C.-M. Phosphorescent platinum(II) materials for OLED applications. In Highly efficient OLEDs with phosphorescent materials; H., Yersin, Ed.; Wiley-VCH: Weinheim, 2008.
29. (b) Williams, J. A. G.; Develay, S.; Rochester, D. L.; Murphy, L. Coord. Chem. Rev. [Online early access]. DOI: 10.1016/j.ccr.2008.03.014. Published Online: 2008; in press.
30. Williams, J. A. G.; Beeby, A.; Davies, E. S.; Weinstein, J. A.; Wilson, C. Inorg. Chem. 2003, 42, 8609.
31. (a) Sotoyama, W.; Satoh, T.; Sawatari, N.; Inoue, H. Appl. Phys. Lett. 2005, 86, 153505.
32. (b) Cocchi, M.; Virgili, D.; Fattori, V.; Rochester, D. L.; Williams, J. A. G. Adv. Funct. Mater. 2007, 17, 285.
33. (c) Kalinowski, J.; Cocchi, M.; Virgili, D.; Fattori, V.; Williams, J. A. G. Chem. Phys. Lett. 2006, 432, 110.
34. (d) Chem. Phys. Lett., 2007, 447, 279.
35. Farley, S. J.; Rochester, D. L.; Thompson, A. L.; Howard, J. A. K.; Williams, J. A. G. Inorg. Chem. 2005, 44, 9690.
36. (a) Cocchi, M.; Virgili, D.; Fattori, V.; Williams, J. A. G.; Kalinowski, J. Appl. Phys. Lett. 2007, 90, 023506.
37. (b) Cocchi, M.; Kalinowski, J.; Virgili, D.; Williams, J. A. G. Appl. Phys. Lett. 2008, 92, 113302.
38. (a) Cocchi, M.; Kalinowski, J.; Virgili, D.; Fattori, V.; Develay, S.; Williams, J. A. G. Appl. Phys. Lett. 2007, 90, 163508.
39. (b) Virgili, D.; Cocchi, M.; Fattori, V.; Sabatini, S.; Kalinowski, J.; Williams, J. A. G. Chem. Phys. Lett. 2006, 433, 145.
40. (c) Kalinowski, J.; Cocchi, M.; Virgili, D.; Fattori, V.; Williams, J. A. G. Adv. Mater. 2007, 19, 4000.
41. For a recent review of pyridyl azolates in the preparation of luminescent complexes, see: (a) Chi, Y.; Chou, P. T. Chem. Soc. Rev. 2007, 36, 1421.
42. (a) Wu, P.-C.; Yu, J.-K.; Song, Y.-H.; Chi, Y.; Chou, P.-T.; Peng, S.-M.; Lee, G.-H. Organometallics 2003, 22, 4938.
43. (b) 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.
44. (c) Chang, S.-Y.; Kavitha, J.; Li, S.-W.; Hsu, C.-S.; Chi, Y.; Yeh, Y.-S.; Chou, P.-T.; Lee, G.-H.; Carty, A. J.; Tao, Y.-T.; Chien, C.-H. Inorg. Chem. 2006, 45, 137.
45. (d) 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.
46. (a) Coppo, P.; Plummer, E. A.; De Cola, L. Chem. Commun. 2004, 1774.
47. (b) Orselli, E.; Kottas, G. S.; Konradsson, A. E.; Coppo, P.; Frǒhlich, R.; De Cola, L.; van Dijken, A.; Büchel, M.; Börner, H. Inorg. Chem. 2007, 46, 11082.
48. Stagni, S.; Orselli, E.; Palazzi, A.; De Cola, L.; Zacchini, S.; Femoni, C.; Marcaccio, M.; Paolucci, F.; Zanarini, S. Inorg. Chem. 2007, 46, 9126.
49. (a) Chang, S.-Y.; Kavitha, J.; Hung, J.-Y.; Chi, Y.; Cheng, Y.-M.; Li, E. Y.; Chou, P.-T.; Lee, G.-H.; Carty, A. J. Inorg. Chem. 2007, 46, 7064.
50. (b) Chang, S.-Y.; Chen, J.-L.; Chi, Y.; Cheng, Y.-M.; Lee, G.-H.; Jiang, C.-M.; Chou, P.-T. Inorg. Chem. 2007, 46, 11202.
51. Nonoyama, M.; Takayanagi, H. Transition Met. Chem. 1976, 1, 10.
52. Maestri, M.; Sandrini, D.; Von Zelewsky, A.; Deuschel-Cornioley, C. Inorg. Chem. 1991, 30, 2476.
53. (a) Koo, C.-K.; Lam, B.; Leung, S.-K.; Lam, M.H.-W.; Wong, W.-Y. J. Am. Chem. Soc. 2006, 128, 16434.
54. (b) Koo, C.-K.; Ho, Y.-M.; Chow, C.-F.; Lam, M.H.-W.; Lau, T.-C.; Wong, W.-Y. Inorg. Chem. 2007, 46, 3603.
55. Willison, S. A.; Jude, H.; Antonelli, R. M.; Rennekamp, J. M.; Eckert, N. A.; Krause Bauer, J. A.; Connick, W. B. Inorg. Chem. 2004, 43, 2548.
56. For a review, see: (a) Halcrow, M. A. Coord. Chem. Rev. 2005, 249, 2880.
57. Willison, S. A.; Krause, J. A.; Connick, W. B. Inorg. Chem. 2008, 47, 1258.
58. For a review, see: (a) Lindley, J. Tetrahedron 1984, 40, 1433.
59. Goodbrand, H. B.; Hu, N.-X. J. Org. Chem. 1999, 64, 670.
60. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
61. (b) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.
62. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844.
63. Pleier, A. K.; Glas, H.; Grosche, M.; Sirsch, P.; Thiel, W. R. Synthesis 2001, 1, 55.
64. Cárdenas, D. J.; Echavarren, A. M.; Ramíre de Arellano, M. C. Organometallics 1999, 18, 3337.
65. (a) Wilkinson, A. J.; Goeta, A.; Foster, C. E.; Williams, J. A. G. Inorg. Chem. 2004, 43, 6513.
66. (b) Wilkinson, A. J.; Puschmann, H.; Howard, J. A. K.; Foster, C. E.; Williams, J. A. G. Inorg. Chem. 2006, 45, 8685.
67. (a) Claramunt, R. M.; Sanz, D.; Santa María, M. D.; Jiménez, J. A.; Jimeno, M. L.; Elguero, J. Heterocycles 1998, 47, 301.
68. (b) Echévarría, A.; Elguero, J.; Meutermans, W. J. Heterocycl. Chem. 1993, 30, 957.
69. Rochester, D. L. Ph. D. Thesis, University of Durham, Durham, U.K., 2007.
70. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
71. Similar effects have been observed in 4′-aryl-substituted terpyridyl Pt(II) complexes and substituted bipyridyl Ru(II) complexes: (a) Michalec, J. F.; Bejune, S. A.; Cuttell, D. G.; Summerton, G. C.; Gertenbach, J. A.; Field, J. S.; Haines, R. J.; McMillin, D. R. Inorg. Chem. 2001, 40, 2193.
72. (b) Damrauer, N. H.; Boussie, T. R.; Devenney, M.; McCusker, J. K. J. Am. Chem. Soc. 1997, 119, 8253.
73. Sotoyama, W.; Satoh, T.; Sato, H.; Matsuura, A.; Sawatari, N. J. Phys. Chem. A 2005, 109, 9760.
74. Note added prior to publication: While this manuscript was under review, Haga et al. reported on iridium(III) complexes with closely related 1,3-bis(3-methylpyrazole)aryl ligands. The very low emission quantum yields of these complexes was shown to be due to the presence of a low-lying d-d state, through which thermally-activated non-radiative decay can occur. Yang, L.; Okuda, F.; Kobayashi, K.; Nozaki, K.; Tanabe, Y.; Ishii, Y.; Haga, M. Inorg. Chem. 2008, 47, 7154.
75. (a) Collin, J.-P.; Dixon, I. M.; Sauvage, J.-P.; Williams, J. A. G.; Barigelletti, F.; Flamigni, L. J. Am. Chem. Soc. 1999, 121, 5009.
76. (b) Goodall, W.; Batsanov, A. S.; Howard, J. A. K.; Williams, J. A. G. Dalton Trans. 2004, 623.
77. (c) Williams, J. A. G.; Wilkinson, A. J.; Whittle, V. L. Dalton Trans. 2008, 2081.
78. Lytle, F. E.; Hercules, D. M. J. Am. Chem. Soc. 1969, 91, 253.
79. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467.
80. Sheldrick, G. M. Computer Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany.
81. Meech, S.; Phillips, D. J. Photochem. 1983, 23, 193.
82. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker: New York, 1993.