Synthesis and characterization of cyclometalated Ir(III) complexes with pyrazolyl ancillary ligands

Polyhedron

Volumn 23, Issue 2-3, 2004, Pages 419-428

  Li, Jian ^a   Djurovich, Peter I ^a   Alleyne, Bert D ^a   Tsyba, Irina ^a   Ho, Nam N ^a   Bau, Robert ^a   Thompson, Mark E ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

Boat conformations; Cyclometalated Ir(II) complexes; Electroluminescence; Iridium; Luminescent; Pyrazolyl ancillary ligands

Indexed keywords

CHELATION; CHLORINE COMPOUNDS; CONFORMATIONS; DIHEDRAL ANGLE; DIMERS; ELECTROLUMINESCENCE; HYDROGEN BONDS; IRIDIUM COMPOUNDS; PHOSPHORESCENCE; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

ANCILLARY LIGANDS; BOAT CONFORMATIONS; BORATE LIGANDS; CHAIR CONFORMATIONS; CYCLOMETALATED IR(II) COMPLEX; IR COMPLEXES; LUMINESCENT; PYRAZOLYL; PYRAZOLYL ANCILLARY LIGAND; SYNTHESIS AND CHARACTERIZATIONS;

LIGANDS;

BORIC ACID; CHLORIDE; IRIDIUM COMPLEX; LIGAND; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON; HYDROLYSIS; PROTON TRANSPORT; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0842332882     PISSN: 02775387     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.poly.2003.11.028     Document Type: Article

References (81)

1. Trofimenko S. J. Am. Chem. Soc. 89:1967;3170.
2. Trofimenko S. Chem. Rev. 93:1993;943.
3. Trofimenko S. Scorpionates: The Coordination Chemistry of Polypyrazolylborate Ligands. 1999;Imperial College Press, London. p. 943.
4. Trofimenko S. Prog. Inorg. Chem. 34:1986;115.
5. Shaver A. Comprehensive Coordination Chemistry, vol 2. 1987;Pergamon, New York.
6. Ritter S.K. CE & EN News. 81(17):2003;40.
7. Cotton F.A., Wilkinson G., Bochman M., Murillo C.A. Advanced Inorganic Chemistry. 1999;Wiley-Interscience, New York.
8. Kitajima N., Tolman W.B. Prog. Inorg. Chem. 43:1995;419.
9. Parkin G. Adv. Inorg. Chem. 42:1995;291.
10. Onishi M., Kumagae S., Asai K., Kawano H., Shigemitsu Y. Chem. Lett. 2001;96.
11. Paneque M., Sirol S., Trujillo M., Gutierrez-Puebla E., Monge M.A., Carmona E. Angew. Chem., Int. Ed. 39:2000;218.
12. Vicente J., Chicote M.T., Guerrero R., Herber U., Bautista D. Inorg. Chem. 41:2002;1870.
13. Effendi G.G.L., Lobbia G.G., Pettinari C., Santini C., Skelton B.W., White A.H. J. Chem. Soc., Dalton Trans. 1998;2739.
14. Kitano T., Sohrin Y., Hata Y., Kawakami H., Hori T., Ueda K. J. Chem. Soc., Dalton Trans. 2001;3564.
15. Tellers D.M., Bergman R.G. J. Am. Chem. Soc. 123:2001;11508.
16. Tellers D.M., Bergman R.G. J. Am. Chem. Soc. 122:2000;954.
17. Wiley J.S., Heinekey D.M. Inorg. Chem. 41:2002;4961.
18. Gutierrez-Puebla E., Monge A., Paneque M., Poveda M.L., Salazar V., Carmona E. J. Am. Chem. Soc. 121:1999;248.
19. Tellers D.M., Bergman R.G. Organometallics. 20:2001;4819.
20. Bowden A.A., Hughes R.P., Lindner D.C., Incarvito C.D., Liable-Sands L.M., Rheingold A.L. J. Chem. Soc., Dalton Trans. 2002;3245.
21. Huang L., Seward K.J., Sullivan B.P., Jones W.E., Mecholsky J.J., Dressick W.J. Inorg. Chim. Acta. 310:2000;227.
22. Moliner N., Salmon L., Capes L., Munoz M.C., Letard J.-F., Bousseksou A., Tuchagues J.-P., McGarvey J.J., Dennis A.C., Castro M., Burriel R., Real J.A. J. Phys. Chem. B. 106:2002;4276.
23. Armaroli N., Accorsi G., Barigelletti F., Couchman S.M., Fleming J.S., Harden N.C., Jeffrey J.C., Mann K.L.V., McCleverty J.A., Rees L.H., Starling S.R., Ward M.D. Inorg. Chem. 38:1999;5769.
24. Reeves Z.R., Mann K.L.V., Jeffrey J.C., McCleverty J.A., Ward M.D., Barigelletti F., Armaroli N. J. Chem. Soc., Dalton Trans. 1999;349.
25. Cecchi P., Bovio B., Lobbia G.G., Pettinari C., Leonesi D. Polyhedron. 14(17):1995;2441.
26. Sprouse S., King K.A., Spellane P.J., Watts R.J. J. Am. Chem. Soc. 106:1984;6647.
27. Lamansky S., Djurovich P., Murphy D., Abdel-Razzaq F., Kwong R., Tsyba I., Bortz M., Mui B., Bau R., Thompson M.E. Inorg. Chem. 40:2001;1704.
28. Grushin V.V., Herron N., LeCloux D.D., Marshall W.J., Petrov V.A., Wang Y. Chem. Commun. 2001;1494.
29. Wang Y., Herron N., Grushin V.V., LeCloux D., Petrov V. Appl. Phys. Lett. 79:2001;449.
30. Ostrowski J.C., Robinson M.R., Heeger A.J., Bazan G.C. Chem. Commun. 2002;784.
31. Adachi C., Kwong R.C., Djurovich P., Adamovich V., Baldo M.A., Thompson M.E., Forrest S.R. Appl. Phys. Lett. 79:2001;2082.
32. Sutin N. Acc. Chem. Res. 1:1968;225.
33. Meyer T.J. Acc. Chem. Res. 11:1978;94.
34. Schmid B., Garces F.O., Watts R.J. Inorg. Chem. 33:1994;9.
35. Belmore K.A., Vanderpool R.A., Tsai J.-C., Khan M.A., Nicholas K.M. J. Am. Chem. Soc. 110:1988;2004.
36. Silavwe N.D., Goldman A.S., Ritter R., Tyler D.R. Inorg. Chem. 28:1989;1231.
37. Demas J.N., Harris E.W., McBride R.P. J. Am. Chem. Soc. 99:1977;3547.
38. Demas J.N., Harris E.W., Flynn C.M., Diemente J.D. J. Am. Chem. Soc. 97:1975;3838.
39. Gao R., Ho D.G., Hernandez B., Selke M., Murphy D., Djurovich P.I., Thompson M.E. J. Am. Chem. Soc. 124:2002;14828.
40. Baldo M.A., O'Brien D.F., You Y., Shoustikov A., Sibley S., Thompson M.E., Forrest S.R. Nature. 395:1998;151.
41. Baldo M.A., Lamansky S., Burrows P.E., Thompson M.E., Forrest S.R. Appl. Phys. Lett. 75:1999;4.
42. Thompson M.E., Burrows P.E., Forrest S.R. Curr. Opin. Solid State Mater. Sci. 4:1999;369.
43. Baldo M.A., Thompson M.E., Forrest S.R. Nature. 403:2000;750.
44. Lamansky S., Djurovich P.I., Abdel-Razzaq F., Garon S., Murphy D.L., Thompson M.E. J. Appl. Phys. 92:2002;1570.
45. Chen F.C., Yang Y., Thompson M.E., Kido J. Appl. Phys. Lett. 80:2002;2308.
46. Markham J.P.J., Lo S.-C., Magennis S.W., Burn P.L., Samuel I.D.W. Appl. Phys. Lett. 80:2002;2645.
47. Zhu W., Mo Y., Yuan W., Cao Y. Appl. Phys. Lett. 80:2002;2045.
48. Lane P.A., Palilis L.C., O'Brien D.F., Giebeler C., Cadby A.J., Lidzey D.G., Campbell A.J., Blau W., Bradley D.D.C. Phys. Rev. B. 63:2001;235206.
49. Adachi C., Baldo M.A., Forrest S.R., Thompson M.E. Appl. Phys. Lett. 77:2000;904.
50. Colombo M.G., Brunold T.C., Riendener T., Gudel H.U., Fortsch M., Burgi H.-B. Inorg. Chem. 33:1994;545.
51. Sheldrick G.M. SHELXTL, version 5.1. 1997;Bruker Analytical X-ray System, Inc. Madison, WI.
52. Blessing R.H. Acta Crystallogr., A. 51:1995;33.
53. Lohse O., Thevenin P., Waldvogel E. Synlett. 1:1999;45.
54. Breakell K.R., Patmore D.J., Storr A. J. Chem. Soc., Dalton Trans. 1975;749.
55. Komorowski L., Maringgele W., Meller A., Niedenzu K., Serwatowski J. Inorg. Chem. 29:1990;3845.
56. Nonoyama M. Bull. Chem. Soc. Jpn. 47:1974;767.
57. Carmona D., Oro L.A., Lamata M.P., Elguero J., Apreda M.C., Foces C., Cano F.H. Angew. Chem., Int. Ed. Engl. 25:1986;1114.
58. Esteruelas M.A., Olivan M., Onate E., Ruiz N., Tajada M.A. Organometallics. 18:1999;2953.
59. Ardizzoia G.A., Brenna S., LaMonica G., Maspero A., Masciocchi N., Moret M. Inorg. Chem. 41:2002;610.
60. Ruiz J., Florenciano F., Rodriguez V., Haro C.D., Lopez G., Perez J. Eur. J. Inorg. Chem. 10:2002;2736.
61. Tamayo A.B., Alleyne B.D., Djurovich P.I., Lamansky S., Tsyba I., Ho N.H., Bau R., Thompson M.E. J. Am. Chem. Soc. 125:2003;7377.
62. The N N distance of a proton sponge, i.e., protonated N,N-9-bis(benzylmethyl)-1,8-diaminonaphthalene iodide, is 2.65 Å, while the N N distance of neutral compound, i.e., N,N-9-bis(benzylmethyl)-1,8- diaminonaphthalene, is 2.81 Å. Ref: Charmant J.P.H., Lloyd-Jones G.C., Peakman T.M., Woodward R.L. Tetrahedron Lett. 39:1998;4733.
63. Charmant J.P.H., Lloyd-Jones G.C., Peakman T.M., Woodward R.L. Eur. J. Org. Chem. 10:1999;2501.
64. Cotton F.A., Luck R.L. Inorg. Chem. 28:1989;3210.
65. Cotton F.A., LaCour T., Stanislowski A.G. J. Am. Chem. Soc. 96:1974;754.
66. Cotton F.A. Inorg. Chem. 41:2002;643.
67. Cotton F.A., Mott G.N. Inorg. Chem. 22:1983;1136.
68. Davies B.W., Payne N.C. J. Organomet. Chem. 102:1975;245.
69. Echols H.M., Dennis D. Acta Crystallogr., B. 30:1974;2173.
70. Paulo A., Domingos A., Santos I. Inorg. Chem. 35:1996;1798.
71. Lobbia G.G., Cecchi P., Giordano F., Santini C. J. Organomet. Chem. 515:1996;213.
72. Effendi G.G.L., Lobbia G.G., Pellei M., Pettinari C., Santini C., Skelton B.W., White A.H. Inorg. Chim. Acta. 315:2001;153.
73. Dungan C.H., Maringgele W., Meller A., Niedenzu K., Noth H., Serwatowska J., Serwatowski J. Inorg. Chem. 30:1991;4799.
74. Ohsawa Y., Sprouse S., King K.A., DeArmond M.K., Hanck K.W., Watts R.J. J. Phys. Chem. 91:1987;1047.
75. Hay P.J. J. Phys. Chem. A. 106:2002;1634.
76. Brooks J., Babayan Y., Lamansky S., Djurovich P.I., Tsyba I., Bau R., Thompson M.E. Inorg. Chem. 41:2002;3055.
77. Holmes R.J., D'Andrade B.W., Forrest S.R., Ren X., Li J., Thompson M.E. Appl. Phys. Lett. 83:2003;3818.
78. Subhan M.A., Suzuki T., Kaizaki S. J. Chem. Soc., Dalton Trans. 2002;1416.
79. Sanada T., Suzuki T., Yoshida T., Kaizaki S. Inorg. Chem. 37:1998;4712.
80. Klink S.I., Keizer H., van Veggel F.C.J.M. Angew. Chem., Int. Ed. 39(23):2000;4319.
81. Kercher M., Konig B., Zieg H., DeCola L. J. Am. Chem. Soc. 124:2002;11541.