Cyclometalated Ir(III) complexes containing N-aryl picolinamide ancillary ligands

Journal of Organometallic Chemistry

Volumn 696, Issue 14, 2011, Pages 2711-2719

  Chandrasekhar, Vadapalli ^a   Mahanti, Bani ^a   Bandipalli, Priyanka ^b   Bhanuprakash, Kotamarthi ^b   Nair, Nisanth N ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Absorption; Cyclometalated; Emission; Lifetime; N Aryl picolinamide; Time dependent DFT

Indexed keywords

ANCILLARY LIGANDS; COORDINATION ENVIRONMENT; CYCLOMETALATED; DENSITY FUNCTIONAL THEORY CALCULATIONS; EMISSION SPECTRUMS; HETEROLEPTIC COMPLEXES; IR(PPY); LIFETIME; LOW ENERGIES; N-ARYL PICOLINAMIDE; OPTICAL SPECTROSCOPIC STUDIES; ORBITALS; TIME DEPENDENT DFT; TRIPLET EXCITATION; ULTRAVIOLET REGION;

CHLORINE COMPOUNDS; DENSITY FUNCTIONAL THEORY; EMISSION SPECTROSCOPY; IRIDIUM COMPOUNDS; LIGANDS; NITROGEN OXIDES; QUANTUM YIELD; SPECTROSCOPIC ANALYSIS;

IRIDIUM;

EID: 79958047582     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.04.011     Document Type: Article

References (87)

1. L. Flamigni, A. Barbieri, C. Sabatini, B. Ventura, and F. Barigelletti Top. Curr. Chem. 281 2007 143 204
2. I.M. Dixon, J.P. Collin, J.P. Sauvage, L. Flamigni, S. Encinas, and F. Barigelletti Chem. Soc. Rev. 29 2000 385 391
3. C. Adachi, M.A. Baldo, S.R. Forrest, and M.E. Thompson Appl. Phys. Lett. 77 2000 904 906
4. M.A. Baldo, S. Lamansky, P.E. Burrows, M.E. Thompson, and S.R. Forrest Appl. Phys. Lett. 75 1999 4 6
5. P.T. Chou, and Y. Chi Chem. Eur. J. 13 2007 380 395
6. R.C. Evans, P. Douglas, and C.J. Winscom Coord. Chem. Rev. 250 2006 2093 2126
7. M. Nazeeruddin, R.T. Wegh, Z. Zhou, C. Klein, Q. Wang, F. De. Angelis, S. Fantacci, and M. Grätzel Inorg. Chem. 45 2006 9245 9250
8. D. Di. Censo, S. Fantacci, F. De. Angelis, C. Klein, N. Evans, K. Kalyanasundaram, H.J. Bolink, M. Grätzel, and M.K. Nazeeruddin Inorg. Chem. 47 2008 980 989
9. H.J. Bolink, L. Cappelli, E. Coronado, M. Grätzel, E. Orti, R.D. Costa, P.M. Viruela, and M.K. Nazeeruddin J. Am. Chem. Soc. 128 2006 14786 14787
10. M.M. Richter Chem. Rev. 104 2004 3003 3036
11. A. Kapturkiewicz, and G. Angulo Dalton Trans. 2003 3907 3913
12. J.I. Goldsmith, W.R. Hudson, M.S. Lowry, T.H. Anderson, and S. Bernhard J. Am. Chem. Soc. 127 2005 7502 7510
13. Y. Chi, and P.T. Chou Chem. Soc. Rev. 36 2007 1421 1431
14. E.I. Mayo, K. Kilsa, T. Tirrell, P.I. Djurovich, A. Tamayo, M.E. Thompson, N.S. Lewis, and H.B. Gray Photochem. Photobiol. Sci. 5 2006 871 873
15. M.X. Yu, Q. Zhao, L.X. Shi, F.Y. Li, Z.G. Zhou, H. Yang, T. Yia, and C.H. Huang Chem. Commun. 2008 2115 2117
16. K.K. Lo, K.K.W. Lo, and J.S.Y. Lau Inorg. Chem. 46 2007 700 709
17. K.K.W. Lo, K.Y. Zhang, C.K. Chung, and K.Y. Kwok Chem. Eur. J. 13 2007 7110
18. K.K.W. Lo, C.K. Chung, and N. Zhu Chem.Eur. J. 12 2006 1500 1512
19. T. Liu, B.H. Xia, Q.C. Zheng, X. Zhou, Q.J. Pan, and H.X. Zhang J. Comput. Chem. 31 2010 628 638
20. P.J. Hay J. Phys. Chem. A 106 2002 1634 1641
21. M.S. Lowry, and S. Bernard Chem. Eur. J. 12 2006 7970 7977
22. T.H. Kwon, H.S. Cho, M.K. Kim, J.W. Kim, J.J. Kim, K.H. Lee, S.J. Park, I.S. Shin, H. Kim, D.M. Shin, Y.K. Chung, and J.I. Hong Organometallics 24 2005 1578 1585
23. A. Tsuboyama, H. Iwawaki, M. Furugori, T. Mukaide, J. Kamatani, S. Igawa, T. Moriyama, S. Miura, T. Takiguchi, S. Okada, M. Hoshino, and K. Ueno J. Am. Chem. Soc. 125 2003 12971 12979
24. T. Sajoto, P.I. Djurovich, A. Tamayo, M. Yousufuddin, R. Bau, M.E. Thompson, R.J. Holmes, and S.R. Forrest Inorg. Chem. 44 2005 7992 8003
25. A.B. Tamayo, B.D. Alleyne, P.I. Djurovich, S. Lamansky, I. Tsyba, N.N. Ho, R. Bau, and M.E. Thompson J. Am. Chem. Soc. 125 2003 7377 7387
26. B. Liang, C.Y. Jiang, Z. Chen, X.J. Zhang, H.H. Shi, and Y. Cao J. Mater. Chem. 16 2006 1281 1286
27. Z.W. Liu, M. Guan, Z.Q. Bian, D.B. Nie, Z.L. Gong, Z.B. Li, and C.H. Huang Adv. Funct. Mater. 16 2006 1441 1448
28. Y.H. Song, S.J. Yeh, C.T. Chen, Y. Chi, C.S. Liu, J.K. Yu, Y.H. Hu, P.T. Chou, S.M. Peng, and G.H. Lee Adv. Funct. Mater. 14 2004 1221 1226
29. C.F. Chang, Y.M. Cheng, Y. Chi, Y.C. Chiu, C.C. Lin, G.H. Lee, P.T. Chou, C.C. Chen, C.H. Chang, and C.C. Wu Angew. Chem. Int. Ed. 47 2008 4542 4545
30. E. Orselli, G.S. Kottas, A.E. Konradsson, P. Coppo, R. Fröhlich, L. De Cola, A. van Dijken, and M.H. Börner Inorg. Chem. 46 2007 11082 11093
31. C.H. Yang, Y.M. Cheng, Y. Chi, C.J. Hsu, F.C. Fang, K.T. Wong, P.T. Chou, C.H. Chang, M.H. Tsai, and C.C. Wu Angew. Chem. Int. Ed. 46 2007 2418 2421
32. R. Ragni, E.A. Plummer, K. Brunner, J.W. Hofstraat, F. Babudri, G.M. Farinola, F. Naso, and L. De Cola J. Mater. Chem. 16 2006 1161 1170
33. C.H. Yang, S.W. Li, Y. Chi, Y.M. Cheng, Y.S. Yeh, P.T. Chou, G.H. Lee, C.H. Wang, and C.F. Shu Inorg. Chem. 44 2005 7770 7780
34. C. Dragonetti, L. Falciola, P. Mussini, S. Righetto, D. Roberto, R. Ugo, A. Valore, F. De Angelis, S. Fantacci, A. Sgamellotti, M. Ramon, and M. Muccini Inorg. Chem. 46 2007 8533 8547
35. Q. Zhao, S. Liu, M. Shi, C. Wang, M. Yu, L. Li, F. Li, T. Yi, and C. Huang Inorg. Chem. 45 2006 6152 6160
36. A.B. Tamayo, S. Garon, T. Sajoto, P.I. Djurovich, I.M. Tsyba, R. Bau, and M.E. Thompson Inorg. Chem. 44 2005 8723 8732
37. Md.K. Nazeeruddin, R. Humphry-Baker, D. Berner, S. Rivier, L. Zuppiroli, and M. Grätzel J. Am. Chem. Soc. 125 2003 8790 8797
38. G. Volpi, C. Garino, L. Salassa, J. Fiedler, K.I. Hardcastle, R. Gobetto, and C. Nervi Chem. Eur. J. 15 2009 6415 6427
39. Y. You, and S.Y. Park J. Am. Chem. Soc. 127 2005 12438 12439
40. Wei Yang, Hao Fu, Qijun Song, Min Zhang, and Yuqiang Ding Organometallics 30 2011 77 83 (During the preparation of this manuscript this article appeared)
41. D.W. Margerum Pure Appl. Chem. 55 1983 23 24
42. T.J. Collins Acc. Chem. Res. 35 2002 782 790
43. M.J. Bartos, S.W. Gordon-Wylie, B.G. Fox, L.J. Wright, S.T. Weintraub, K.E. Kauffmann, E. Münck, K.L. Kosta, E.S. Uffelman, C.E.F. Rickard, K.R. Noon, and T.J. Collins Coord. Chem. Rev. 174 1998 361 390
44. T.J. Collins Acc. Chem. Res. 27 1994 279 285
45. M.H. Chou, D.J. Szalda, C. Creutz, and N. Sutin Inorg. Chem. 33 1994 1674 1684
46. P.C. Ford, D.P. Rudd, R. Gaunder, and H. Taube J. Am. Chem. Soc. 90 1968 1187 1194
47. A.K. Singh, V. Balamurugan, and R. Mukherjee Inorg. Chem. 42 2003 6497 6502
48. H. Sigel Inorg. Chem. 14 1975 1535 1540
49. H. Sigel, C.F. Naumann, B. Prijs, D.B. McCormick, and M.C. Falk Inorg. Chem. 16 1977 790 796
50. M.F. El-Shazly, El. Dissowky, T. Salem, and M. Osman Inorg. Chim. Acta 40 1980 1 6
51. A. White, X. Ding, J.C. vanderSpek, J.R. Murphy, and D. Ringe Nature 394 1998 502 506
52. E. Pohl, R.K. Holmes, and W.G.J.J. Hol Mol. Biol. 292 1999 653 667
53. S.H.V. Rijt, A. Hebden, T. Amaresekera, R.J. Deeth, G.J. Clarkson, S. Parsons, P.C. McGowan, and P.J. Sadler J. Med. Chem. 52 2009 7753 7764
54. P. Srinivas, P.R. Likhar, H. Maheswaran, B. Sridhar, K. Ravikumar, and M.L. Kantam Chem. Eur. J. 15 2009 1578 1581
55. M.L. Kantam, P. Srinivas, J. Yadav, P.R. Likhar, and S. Bhargava J. Org. Chem. 74 2009 4882 4885
56. S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, R. Kwong, I. Tsyba, M. Bortz, B. Mui, R. Bau, and M.E. Thompson Inorg. Chem. 40 2001 1704 1711
57. J. Breu, P. Stossel, S. Schrader, A. Starukhin, W.J. Finkenzeller, and H. Yersin Chem. Mater 17 2005 1745 1757
58. D.G.H. Hetterscheid, J. Kaiser, E. Reijerse, T.P.J. Peters, S. Thewissen, A.N.J. Blok, J.M.M. Smits, R. De. Gelder, and B. De. Bruin J. Am. Chem. Soc. 127 2005 1895 1905
59. S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, H.E. Lee, C. Adachi, P.E. Burrows, S.R. Forrest, and M.E. Thompson J. Am. Chem. Soc. 123 2001 4304 4312
60. M. Lepeltier, T.K.M. Lee, K.K.W. Lo, L. Toupet, H. Le Bozec, and V. Guerchais Eur. J. Inorg. Chem. 2005 110 117
61. W.S. Sie, J.Y. Jian, T.C. Su, G.H. Lee, H.M. Lee, and K.B. Shiu J. Org. Chem. 693 2008 1510 1517
62. M.G. Colombo, A. Hauser, and H.U. Guedel Inorg. Chem. 32 1993 3088 3092
63. L. Flamigni, B. Ventura, F. Barigelletti, E. Baranoff, J.P. Collin, and J.P. Sauvage Eur. J. Inorg. Chem. 2005 1312 1318
64. J.P. Collman, C.E. Barnes, P.N. Swepston, and J.A. Ibers J. Am. Chem. Soc. 106 1984 3500 3510
65. J. Li, P.I. Djurovich, B.D. Alleyne, M. Yousufuddin, N.N. Ho, J.C. Thomas, J.C. Peters, R. Bau, and M.E. Thompson Inorg. Chem. 44 2005 1713 1727
66. X. Ren, D.J. Giesen, M. Rajeswaran, and M. Madaras Organometallics 28 2009 6079 6089
67. S. Nag, R. Butcher, and S. Bhattacharya Eur. J. Inorg. Chem. 2007 1251 1260
68. W.H. Smith, and A.J. Bard J. Am. Chem. Soc. 97 1975 5203 5210
69. A.S. Mendkovich, L.V. Michalchenko, and V.P. Gultyai J. Electroanal. Chem. 224 1987 273
70. A.I. Vogel Vogel's Textbook f Practical Organic Chemistry fifth ed. 1989 Longman London
71. I.B. Berlman Handbook of Fluorescence Spectra of Aromatic Molecules 1965 Academic Press New York
72. W.H. Melhuish J. Phys. Chem. 65 1961 229
73. Smart & SAINT Software Reference Manuals, Version 6.45 2003 Bruker Analytical X-ray Systems, Inc. Madison, WI
74. G.M. Sheldrick SADABS, a Software for Empirical Absorption Correction, Version. 2.05 2002 University of Göttingen Göttingen, Germany
75. G.M. Sheldrick SHELXTL Reference Manual, Version. 6.1 2000 Bruker Analytical X-ray Systems, Inc. Madison, WI
76. G.M. Sheldrick SHELXTL Ver. 6.12 2001 Bruker Analytical X-ray Systems, Inc. Madison, WI
77. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
78. A.D. Becke J. Chem. Phys. 98 1993 5648 5653
79. J.P. Perdew, K. Burke, and M. Ernerhof Phys. Rev. Lett. 78 1997 1396
80. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 299 310
81. P.J. Hay, and W.R. Wadt J. Chem. Phys. 82 1985 270 283
82. V. Barone, and M. Cossi J. Chem. Phys. 107 1997 3210 3221
83. M. Cossi, G. Scalmani, N. Regar, and V. Barone J. Chem. Phys. 117 2002 43 54
84. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Forestman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzales, and J.A. Pople Gaussian 03, Revision D.01 2004 Gaussian Inc. Wallingford CT
85. N.M. O'Boyle, A.L. Tenderholt, and K.M. Langner J. Comp. Chem. 29 2008 839 845
86. M. Nonoyama Bull. Chem. Soc. Jpn. 47 1974 767 768
87. S. Dutta, S. Pal, and P.K. Bhattacharya Polyhedron 18 1999 2157 2162