Electronic structures and optical properties of neutral substituted fluorene-based cyclometalated platinum(II)-acetylide complexes: A DFT exploration

Journal of Organometallic Chemistry

Volumn 694, Issue 12, 2009, Pages 1848-1860

  Bai, Fu Quan ^a   Zhou, Xin ^a   Xia, Bao Hui ^a   Liu, Tao ^a   Zhang, Jian Po ^a   Zhang, Hong Xing ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

Acetylide; DFT; Electronic structures; Fluorene; Optical properties; Platinum

Indexed keywords

ABSORPTION TRANSITIONS; ACETYLIDE; ACETYLIDE LIGANDS; BIPYRIDINE; DFT; DFT STUDIES; DI-NUCLEAR COMPLEXES; DINUCLEAR; ELECTRONIC DELOCALIZATION; ELECTRONIC LOCALIZATIONS; FIRST HYPERPOLARIZABILITIES; FLUORENE; MOLECULAR GEOMETRIES; NON-LINEAR OPTICAL MATERIALS; OSCILLATOR STRENGTHS; PHOSPHORESCENT EMISSIONS; PLATINUM-COMPLEXES; REVERSE PROCESS; TRANSITION ENERGIES; TRANSITION MOMENTS; TRIPLE BONDS; TRIPLET STATE;

ELECTRONIC PROPERTIES; ELECTRONIC STRUCTURE; ENERGY ABSORPTION; OPTICAL MATERIALS; OPTICAL PROPERTIES; OSCILLATORS (ELECTRONIC); PLATINUM; PROBABILITY DENSITY FUNCTION; SEMICONDUCTOR QUANTUM DOTS; STRUCTURAL PROPERTIES;

PLATINUM COMPOUNDS;

EID: 64849110452     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2009.01.020     Document Type: Article

References (124)

1. Nast R. Coord. Chem. Rev. 47 (1982) 89
2. Nguyen P., Gomez-Elipe P., and Manners I. Chem. Rev. 99 (1999) 1515
3. Bunz U.H.F., Rubin Y., and Tobe Y. Chem. Soc. Rev. 28 (1999) 107
4. Bruneau C., and Dixneuf P.H. Acc. Chem. Res. 32 (1999) 311
5. Manners I. Angew. Chem., Int. Ed. Engl. 35 (1996) 1602
6. Schwab P.F.H., Levin M.D., and Michl J. Chem. Rev. 99 (1999) 1869
7. Yamamoto T. Bull. Chem. Soc. Jpn. 72 (1999) 621
8. Lichtenberger D.L., Renshaw S.K., Wong A., and Tagge C.D. Organometallics 12 (1993) 3522
9. Lichtenberger D.L., Renshaw S.K., and Bulluck R.M. J. Am. Chem. Soc. 115 (1993) 3276
10. Kim P.J., Masai H., Sonogashira K., and Hagihara N. Inorg. Nucl. Chem. Lett. 6 (1970) 181
11. Long N.J., and Williams C.K. Angew. Chem., Int. Ed. 42 (2003) 2586
12. Long N.J. Angew. Chem., Int. Ed. Engl. 34 (1995) 21
13. Barlow S., and O'Hare D. Chem. Rev. 97 (1997) 637
14. Younus M., Kohler A., Cron S., Chawdhury N., Al-Madani M.R.A., Khan M.S., Long N.J., Friend R.H., and Raithby P.R. Angew. Chem., Int. Ed. 37 (1998) 3036
15. Chawdhury N., Kohler A., Friend R.H., Younus M., Long N.J., Raithby P.R., and Lewis J. Macromolecules 31 (1998) 722
16. Yam V.W.W., Lo K.K.W., and Wong K.M.C. J. Organomet. Chem. 578 (1999) 3
17. Yam V.W.W. Acc. Chem. Res. 35 (2002) 555
18. Irwin M.J., Vittal J.J., and Puddephatt R.J. Organometallics 16 (1997) 3541
19. Paul F., and Lapinte C. Coord. Chem. Rev. 178-180 (1998) 431
20. Tessler N., Denton G.J., and Fried R.H. Nature 382 (1996) 695
21. Chan S.-C., Chan M.C.W., Wang Y., Che C.-M., Cheung K.-K., and Zhu N. Chem. Eur. J. 7 (2001) 4180
22. Yang Y., Zhang D., Wu L.-Z., Chen B., Zhang L.-P., and Tung C.-H. J. Org. Chem. 69 (2004) 4788
23. Zhang D., Wu L.-Z., Zhou L., Han X., Yang Q.-Z., Zhang L.-P., and Tung C.-H. J. Am. Chem. Soc. 126 (2004) 3440
24. Yam V.W.W., Tang R.P.-L., Wong K.M.C., and Cheung K.K. Organometallics 20 (2001) 4476
25. Donhauser Z.J., Mantooth B.A., Kelly K.F., Bumm L.A., Monnell J.D., Stapleton Jr. J.J., Price D.W., Rawlett A.M., Allara D.L., Tour J.M., and Weiss P.S. Science 292 (2001) 2303
26. Zhou G.-J., Wong W.-Y., Ye C., and Lin Z. Adv. Funct. Mater. 17 (2007) 963
27. Tang C.W., and Van Slyke S.A. Appl. Phys. Lett. 51 (1987) 913
28. Lewis J., Khan M.S., Kakkar A.K., Johnson B.F.G., Marder T.B., Fyfe H.B., Wittmann F., Friend R.H., and Dray A.E. J. Organomet. Chem. 425 (1992) 165
29. Frapper G., and Kertesz M. Inorg. Chem. 32 (1993) 732
30. Bunten K.A., and Kakkar A.K. Macromolecules 29 (1996) 2885
31. Chawdhury N., Köhler A., Friend R.H., Wong W.Y., Lewis J., Younus M., Raithby P.R., Corcoran T.C., Al-Mandhary M.R.A., and Khan M.S.J. Chem. Phys. 110 (1999) 4963
32. Wilson J.S., Köhler A., Friend R.H., Al Suti M.K., Al-Mandhary M.R.A., Khan M.S., and Raithby P.R. J. Chem. Phys. 113 (2000) 7627
33. Lu W., Mi B.-X., Chan M.C.W., Hui Z., Che C.-M., Zhu N., and Lee S.-T. J. Am. Chem. Soc. 126 (2004) 4958
34. Evans R.C., Douglas P., and Winscom C.J. Coord. Chem. Rev. 250 (2006) 2093
35. Wong W.-Y., and Ho C.-L. Coord. Chem. Rev. 250 (2006) 2627
36. Masai H., Sonogashira K., and Hagihara N. Bull. Chem. Soc. Jpn. 44 (1971) 2226
37. Sonogashira K., Yatake T., Tohda Y., Takahashi S., and Hagihara N. J. Chem. Soc. Chem. Commun. (1977) 291
38. Sonogashira K., Hagihara N., and Takahashi S. Macromolecules 10 (1977) 879
39. Sonogashira K., Fujikura Y., Yatake T., Toyoshima N., Takahashi S., and Hagihara N. J. Organomet. Chem. 145 (1978) 101
40. Fujikura Y., Sonogashira K., and Hagihara N. Chem. Lett. (1975) 1067
41. Takahashi S., Murata E., Sonogashira K., and Hagihara N. J. Polym. Sci. Polym. Chem. Ed. 18 (1980) 661
42. Chan C.W., Cheng L.K., and Che C.M. Coord. Chem. Rev. 132 (1994) 87
43. Lewis J., Raithby P.R., and Wong W.-Y. J. Organomet. Chem. 556 (1998) 219
44. Wong W.Y., Choi K.H., Lu G.L., and Shi J.X. Macromol. Rapid Commun. 22 (2001) 461
45. Wang C., Yuan C., Wu H., and Wei Y.J. Appl. Lett. 78 (1995) 4264
46. Tao X.-T., Zhang Y.-D., Wada T., Sasabe H., Suzuki H., Watanabe T., and Miyata S. Adv. Mater. 10 (1998) 226
47. Maruyama S., Zhang Y., Wada T., and Sasabe H. J. Chem. Soc., Perkin Trans. 1 (1999) 41
48. Wong W.-Y., Lu G.-L., Choi K.-H., and Shi J.-X. Macromolecules 35 (2002) 3506
49. Ziessel R., Hissler M., El-ghayoury A., and Harriman A. Coord. Chem. Rev. 178-180 (1998) 1251
50. Hissler M., McGarrah J.E., Connick W.B., Geiger D.K., Cummings S.D., and Eisenberg R. Coord. Chem. Rev. 208 (2000) 115
51. McMillin D.R., and Moore J.J. Coord. Chem. Rev. 229 (2002) 113
52. Castellano F.N., Pomestchenko I.E., Shikhova E., Hua F., Muro M.L., and Rajapakse N. Coord. Chem. Rev. 250 (2006) 1819
53. Gereth Williams J.A. Top. Curr. Chem. 281 (2007) 205
54. Lai S.W., Chan M.C.W., Cheung K.K., and Che C.M. Organometallics 18 (1999) 3327
55. Lai S.W., Chan M.C.W., Cheung T.C., Peng S.M., and Che C.M. Inorg. Chem. 38 (1999) 4046
56. Neve F., Ghedini M., and Crispini A. J. Chem. Soc., Chem. Commun. (1996) 2463
57. Cheung T.C., Cheung K.K., Peng S.M., and Che C.M. J. Chem. Soc., Dalton Trans. (1996) 1645
58. Chan C.W., Lai T.F., Che C.M., and Peng S.M. J. Am. Chem. Soc. 115 (1993) 11245
59. Lu W., Chan M.C.W., Cheung K.K., and Che C.M. Organometallics 20 (2001) 2477
60. Yam V.W.W., Tang R.P.L., Wong K.M.C., Ko C.C., and Cheung K.K. Inorg. Chem. 40 (2001) 571
61. Michalec J.F., Bejune S.A., and McMillin D.R. Inorg. Chem. 39 (2000) 2708
62. Arena G., Calogero G., Campagna S., Scolaro L.M., Ricevuto V., and Romeo R. Inorg. Chem. 37 (1998) 2763
63. Seneclauze J.B., Retailleau P., and Ziessel R. New J. Chem. 31 (2007) 1412
64. Bella S.D. Chem. Soc. Rev. 30 (2001) 355 and references therein
65. Powell C.E., and Humphrey M.G. Coord. Chem. Rev. 248 (2004) 725 and references therein
66. Zhou X., Pan Q.-J., Xia B.-H., Li M.-X., Zhang H.-X., and Tung A.-C. J. Phys. Chem. A 111 (2007) 5465
67. Liu X.-J., Feng J.-K., Meng J., Pan Q.-J., Ren A.-M., Zhou X., and Zhang H.-X. Eur. J. Inorg. Chem. (2005) 1856
68. Cardolaccia T., Li Y., and Schanze K.S. J. Am. Chem. Soc. 130 (2008) 2535
69. Amicangelo J.C. J. Chem. Theory Comput. 3 (2007) 2198
70. Stoyanov S.R., Villegas J.M., and Rillema D.P. Inorg. Chem. 42 (2003) 7852
71. Shi L.-L., Liao Y., Yang G.-C., Su Z.-M., and Zhao S.-S. Inorg. Chem. 47 (2008) 2347
72. Koch W., and Holthausen M.C. A Chemist's Guide to Density Functional, Theory (2000), Wiley-VCH, Weinheim, Germany
73. Adamo C., and di Matteo B.V. Adv. Quantum Chem. 36 (1999) 4
74. Runge E., and Gross E.K.U. Phys. Rev. Lett. 52 (1984) 997
75. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785
76. Becke A.D. J. Chem. Phys. 98 (1993) 5648
77. Nozaki K., Takamori K., Nakatsugawa Y., and Ohno T. Inorg. Chem. 45 (2006) 6161
78. Miehlich B., Savin A., Stoll H., and Preuss H. Chem. Phys. Lett. 157 (1989) 200
79. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 270
80. Wadt W.R., and Hay P.J. J. Chem. Phys. 82 (1985) 284
81. Hay P.J., and Wadt W.R. J. Chem. Phys. 82 (1985) 299
82. Hariharan P.C., and Pople J.A. Mol. Phys. 27 (1974) 209
83. Glimsdal E., Carlsson M., Eliasson B., Minaev B., and Lindgren M. J. Phys. Chem. A 111 (2007) 244
84. Cooper T.M., Krein D.M., Burke A.R., McLean D.G., Rogers J.E., and Slagle J.E. J. Phys. Chem. A 110 (2006) 13370
85. He Z., Wong W.-Y., Yu X., Kwok H.-S., and Lin Z. Inorg. Chem. 45 (2006) 10922
86. Hirani B., Li J., Djurovich P.I., Yousufuddin M., Oxgaard J., Persson P., Wilson S.R., Bau R., Goddard III W.A., and Thompson M.E. Inorg. Chem. 46 (2007) 3865
87. Sotoyama W., Satoh T., Sato H., Matsuura A., and Sawatari N. J. Phys. Chem. A 109 (2005) 9760
88. Jamorski C., Casida M.E., and Salahub D.R. J. Chem. Phys. 104 (1996) 5134
89. Petersilka M., Grossmann U.J., and Gross E.K.U. Phys. Rev. Lett. 76 (1996) 1212
90. Bauernschmitt R., Ahlrichs R., Hennrich F.H., and Kappes M.M. J. Am. Chem. Soc. 120 (1998) 5052
91. Casida M.E., Jamorski C., Casida K.C., and Salahub D.R. J. Chem. Phys. 108 (1998) 4439
92. Stratmann R.E., Scuseria G.E., and Frisch M.J. J. Chem. Phys. 109 (1998) 8218
93. Chen W., Li Z.R., Wu D., Li Y., and Sun C.C. J. Phys. Chem. A 109 (2005) 2920
94. Cossi M., Scalmani G., Regar N., and Barone V. J. Chem. Phys. 117 (2002) 43
95. Barone V., Cossi M., and Tomasi J. J. Chem. Phys. 107 (1997) 3210
96. Andrae D., Haussermann U., Dolg M., Stoll H., and Preuss H. Theor. Chim. Acta 77 (1990) 123
97. Dolg M., Pyykkö P., and Runeberg N. Inorg. Chem. 35 (1996) 7450
98. 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, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. 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. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, 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. Gonzalez, J.A. Pople, gaussian 03, revision C.02, Gaussian Inc., Wallingford, CT, 2004.
99. Oda M., Nothofer H.-G., Scherf U., Šunjić V., Richter D., Regenstein W., and Neher D. Macromolecules 35 (2002) 6792
100. Wang J.-F., Feng J.-K., Ren A.-M., Liu X.-J., Ma Y.-G., Lu P., and Zhang H.-X. Macromolecules 37 (2004) 3451
101. Fantacci S., De Angelis F., and Selloni A. J. Am. Chem. Soc. 125 (2003) 4381
102. Charlot M.-F., Pellegrin Y., Quaranta A., Leibl W., and Aukauloo A. Chen. Eur. J. 12 (2006) 796
103. Charlot M.-F., and Aukauloo A. J. Phys. Chem. A 111 (2007) 11661
104. Rosa A., Ricciardi G., Gritsenko O., and Baerends E. J. Struct. Bond. 112 (2004) 49
105. Gisbergen S.J.A., Groeneveld J.A., Rosa A., Snijders J.G., and Baerends E.J. J. Phys. Chem. A 103 (1999) 6835
106. Vlček A., and Zališ S. Coord. Chem. Rev. 251 (2007) 258
107. Casida M.E., Gutierrez F., Guan J., Gadea F.X., Salahub D., and Daudey J.P. J. Chem. Phys. 113 (2000) 7062
108. Cai Z.L., Sendt K., and Reimers J.R. J. Chem. Phys. 117 (2002) 5543
109. Dreuw A., Weisman J.L., and Head-Gordon M. J. Chem. Phys. 119 (2003) 2943
110. Grimme S., and Parac M. ChemPhysChem 3 (2003) 292
111. Piacenza M., Della Sala F., Fabiano E., Maiolo T., and Gigli G. J. Comput. Chem. 29 (2008) 451
112. Grave C., Risko C., Shaporenko A., Wang Y., Nuckolls C., Ratner M.A., Rampi M.A., and Zharnikov M. Adv. Funct. Mater. 17 (2007) 3816
113. Avilov I., Marsal P., Brédas J.L., and Beljonne D. Adv. Mater. 16 (2004) 1624
114. Avilov I., Minoofar P., Cornil J., and Cola L.D. J. Am. Chem. Soc. 129 (2007) 8247
115. Dos Santos D.A., Beljonne D., Cornil J., and Brédas J.L. Chem. Phys. 227 (1998) 1
116. Beljonne D., Cornil J., Brédas J.L., Friend R.H., and Janssen R.A.J. J. Am. Chem. Soc. 118 (1996) 6453
117. Beljonne D., Wittmann H.F., Köhler A., Graham S., Younus M., Lewis J., Raithby P.R., Khan M.S., Friend R.H., and Brédas J.L. J. Chem. Phys. 105 (1996) 3868
118. Whittall I.R., McDonagh A.M., Humphrey M.G., and Samoc M. Adv. Organomet. Chem. 42 (1998) 291
119. Coe B.J. Chem. Eur. J. 5 (1999) 2464
120. Coe B.J., Harris J.A., Asselberghs I., Persoons A., Jeffery J.C., Rees L.H., Gelbrich T., and Hursthouse M.B. J. Chem. Soc., Dalton Trans. (1999) 3617
121. Coe B.J., Harris J.A., Clays K., Persoons A., Wostyn K., and Brunschwig B.S. Chem. Commun. (2001) 1548
122. Oudar J.L., and Chemla D.S. J. Chem. Phys. 66 (1977) 2664
123. Oudar J.L. J. Chem. Phys. 67 (1977) 446
124. Kanis D.R., Ratner M.A., and Marks T.J. Chem. Rev. 94 (1994) 195