Influence of molecular geometry, exchange-correlation functional, and solvent effects in the modeling of vertical excitation energies in phthalocyanines using time-dependent density functional theory (TDDFT) and polarized continuum model TDDFT methods: Can modern computational chemistry methods explain experimental controversies?

Journal of Physical Chemistry A

Volumn 111, Issue 50, 2007, Pages 12901-12913

  Nemykin, Victor N ^a   Hadt, Ryan G ^a   Belosludov, Rodion V ^b   Mizuseki, Hiroshi ^b   Kawazoe, Yoshiyuki ^b  

^a UNIVERSITY OF MINNESOTA DULUTH   (United States)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DENSITY FUNCTIONAL THEORY; DICHROISM; EXCITATION ENERGY; EXCITED STATES; MOLECULAR ORBITALS;

MAGNETIC CIRCULAR DICHROISM; MOLECULAR GEOMETRY; PHTHALOCYANINES; POLARIZED CONTINUUM MODELS;

ZINC COMPOUNDS;

EID: 84961971217     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0759731     Document Type: Article

References (78)

1. Phthalocyanines: Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1990-1996; Vol. 1-4.
2. McKeown, N. B.; Budd, P. M. Chem. Soc. Rev. 2006, 35, 675-683.
3. Kaliya, O. L.; Lukyanets, E. A.; Vorozhtsov, G. N. J. Porphyrins Phthalocyanines 1999, 3, 592-610.
4. (a) Juzenas, P. Trends Cancer Res. 2005, 1, 93-110.
5. (b) O'Riordan, K.; Akilov, O. E.; Hasan, T. Photodiagn. Photodyn. Then 2005, 2, 247-262.
6. (a) Elemans, J. A. A. W.; van Hameren, R.; Nolte, R. J. M.; Rowan, A. E. Adv. Mater. 2006, 18, 1251-1266.
7. (b) Rao, C. N. R.; Govindaraj, A. Acc. Chem. Res. 2002, 35, 998-1007.
8. (a) de la Torre, G.; Vazquez, P.; Agullo-Lopez, F.; Torres, T. J. Mater. Chem. 1998, 8, 1671-1683.
9. (b) Chen, Y.; Hanack, M.; Blau, W. J.; Dini, D.; Liu, Y.; Lin, Y.; Bai, J. J. Mater. Sci. 2006, 41, 2169-2185.
10. (c) Wrobel, D.; Dudkowiak, A. Mol. Cryst. Liq. Cryst. 2006, 448, 617-640.
11. Stillman, M. J. In Phthalocyanines: Properties and Applications; Leznoff, C. C., Lever, A. B. P., Eds.; VCH Publishers: New York, 1993; Vol. 3, Chapter 5, pp 227-296.
12. Anderson, J. S.; Bradbrook, E. F.; Cook, A. H.; Linstead, R. P. J. Chem. Soc. 1938, 1151-1156.
13. Edwards, L.; Gouterman, M. J. Mol. Spectrosc. 1970, 33, 292.
14. Edwards, L.; Dolphin, D. H.; Gouterman, M. J. Mol. Spectrosc. 1970, 35, 90.
15. Nyokong, T. N.; Gasyna, Z.; Stillman, M. J. Inorg. Chem. 1987, 26, 1087.
16. Mack, J.; Stillman, M. J. J. Phys. Chem. 1995, 99, 7935.
17. VanCott, T. C.; Rose, J. L.; Misener, G. C.; Williamson, B. E.; Schrimpf, A. E.; Boyle, M. E.; Schatz, P. N. J. Phys. Chem. 1989, 93, 2999.
18. Fitch, P. S. H.; Wharton, L.; Levy, D. H. J. Chem. Phys. 1978, 69, 3424-3426.
19. Mack, J.; Stillman, M. J. J. Phys. Chem. 1995, 99, 7935.
20. Ricciardi, G.; Rosa, A.; Baerends, E. J. J. Phys. Chem. A 2001, 105, 5242-5254.
21. Keizer, S. P.; Mack, J.; Bench, B. A.; Gorun, S. M.; Stillman, M. J. J. Am. Chem. Soc. 2003, 125, 7067-7085.
22. Mack, J.; Stillman, M. J. Coord. Chem. Rev. 2001, 219-221, 993-1032.
23. (a) Deeth, R. J. Faraday Discuss. 2003, 124, 379-391.
24. (b) Rosa, A.; Ricciardi, G.; Gritsenko, O.; Baerends, E. J. Struct. Bonding 2004, 112, 49-116.
25. (c) Nemykin, V. N.; Basu, P. Inorg. Chem. 2003, 42, 4046-4056.
26. (a) Roitberg, A. E.; Worthington, S. E.; Holden, M. J.; Mayhew, M. P.; Krauss, M. J. Am. Chem. Soc. 2000, 122, 7312-7316.
27. (b) Schlegel, H. B.; Robb, M. A. Chem. Phys. Lett. 1982, 93, 43-46.
28. (a) Shepard, R.; Shavitt, I.; Pitzer, R. M.; Comeau, D. C.; Pepper, M.; Lischka, H.; Szalay, P. G.; Ahlrichs, R.; Brown, F. B.; Zhao, J.-G. Int. J. Quantum Chem. 1988, S2, 149-165.
29. (b) Lischka, H.; Dallos, M.; Shepard, R. Mol. Phys. 2002, 700, 1647-1658.
30. (c) Chang, J.-L.; Chen, Y.-T. J. Chem. Phys. 2002, 116, 7518-7525.
31. (a) Hesselmann, A.; Jansen, G.; Schuetz, M. J. Am. Chem. Soc. 2006, 128, 11730-11731.
32. (b) Podeszwa, R.; Bukowski, R.; Szalewicz, K. J. Chem. Theory Comput. 2006, 2, 400-412.
33. Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009-4037.
34. Nguyen, K. A.; Pachter, R. J. Chem. Phys. 2001, 114, 10757-10767.
35. Mack, J.; Asano, Y.; Kobayashi, N.; Stillman, M. J. J. Am. Chem. Soc. 2005, 127, 17697-17711.
36. Mack, J.; Stillman, M. J.; Kobayashi, N. Coord. Chem. Rev. 2007, 251, 429-453.
37. Kuznetsova, N. A.; Okunchikov, V. V.; Derkacheva, V. M.; Kaliya, O. L.; Lukyanets, E. A. J. Porphyrins Phthalocyanines 2005, 9, 393-397.
38. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
39. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
40. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
41. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
42. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865.
43. (a) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639-5948.
44. (b) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
45. (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981,55, 117-129.
46. (b) Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3094.
47. (a) Ridley, J.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111-134.
48. (b) Zerner, M. C.; Loew, J. H.; Kirchner, E. F.; Mueller-Westerhoff, U. T.; Nazaal, A. J. Am. Chem. Soc. 1980, 102, 589-599.
49. (c) Neto, J. D. M.; Zerner, M. C. Int. J. Quantum Chem. 2001, 81, 187-201.
50. (d) Anderson, W. P.; Edwards, E. D.; Zerner, M. C. Inorg. Chem. 1986, 25, 2728-2732.
51. Stewart, J. J. P. J. Comput.-Aided Mol. Des. 1990, 4, 1-105.
52. Frisch, M. J.; Tracks, 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.
53. HyperChem Pro, version 7.51; HyperCube, Inc.: Gainesville, FL, 2004.
54. Nemykin, V. N.; Basu, P. VMOdes: Virtual Molecular Orbital description program for Gaussian, GAMESS, and HyperChem, revision A 7.1,2004.
55. Origin Pro, version 7.5; OriginLab Corporation: Northampton, MA, 2004.
56. Scheid, W. R.; Dow, W. J. Am. Chem. Soc. 1977, 99, 1101.
57. (a) Wu, Q.; Cohen, A. J.; Yang, W. J. Chem. Phys. 2005, 123, 134111.
58. (b) Dierksen, M.; Grimme, S. J. Phys. Chem. A 2004, 108, 10225-10237.
59. (c) Leszcynski, J.; Goodman, L.; Kwiatkowski, J. S. Theor. Chem. Acc. 1997, 97, 195-202.
60. (d) Lelj, F.; Adamo, C.; Barone, V. Chem. Phys. Lett. 1994, 230, 189-95.
61. Nemykin, V. N.; Hadt, R. G. Inorg. Chem. 2006, 45, 8297-8307.
62. Schlettwein, D.; Hesse, K.; Gruhn, N. E.; Lee, P. A.; Nebesny, K. W.; Armstrong, N. R. J. Phys. Chem. B 2001, 105, 4791-4800.
63. Van, Voorhis, T.; Scuseria, G. E. J. Chem. Phys. 1998, 109, 400.
64. Martin, C. H.; Zerner, M. C. In Inorganic Electronic Structure and Spectroscopy; Solomon, E. I., Lever A. B. P., Eds.; Wiley: New York, 1999; Vol. 1, pp 555-659.
65. (a) Wan, J.; Ren, Y.; Wu, J.; Xu, X. J. Phys. Chem. A 2004, 108, 9453-9460.
66. (b) Chakraborty, A.; Kar, S.; Nath, D. N.; Guchhait, N. J. Phys. Chem. A 2006, 110, 12089-12095.
67. (c) Zhu, Y.; Zhou, S.; Kan, Y.; Su, Z. Int. J. Quantum Chem. 2007,107, 1614-1623.
68. (d) Nemykin, V. N.; Olsen, J. G.; Perera, E.; Basu, P. Inorg. Chem. 2006, 45, 3557-3568.
69. (a) HyperChem Reference Manual; HyperCube, Inc.: Gainesville, FL, 1996.
70. (b) Parr, R. G. The Quantum Chemistry of Molecular Electronic Structure; W. A. Benjamin: New York, 1964; p 510.
71. Yuan, S.; Feng Chen, Z.; Rong. J. Phys. Chem. A 2005, 709, 2582-2585.
72. Browett, W. R.; Stillman, M. J. Comput. Chem. 1987, 77, 241.
73. Ough, E.; Nyokong, T.; Creber, K. A. M.; Stillman, M. J. Inorg. Chem. 1988, 27, 2724-2732.
74. Huang, T. H.; Reickhoff, K. E.; Voigt, E. M. J. Chem. Phys. 1982, 77, 3424-3441.
75. Scheidt, W. R.; Dow, W. J. Am. Chem. Soc. 1977, 36, 413.
76. Cortina, H.; Senent, M. L.; Smeyers, Y. G. J. Phys. Chem. A 2003, 107, 8968.
77. Toyota, K.; Hasegawa, J.; Nakatsuji, H. J. Phys. Chem. A 1997, 707, 446.
78. Parusel, A. B. J.; Grimme, S. J. Porphyrins Phthalocyanines 2001, 5, 225.