Theoretical study of the effects of solvent environment on photophysical properties and electronic structure of paracyclophane chromophores

Journal of Chemical Physics

Volumn 122, Issue 22, 2005, Pages

  Masunov, Artëm ^a   Tretiak, Sergei ^a   Hong, Janice W ^b   Liu, Bin ^b   Bazan, Guillermo C ^b  

^a CENTER FOR NONLINEAR STUDIES   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MOLECULAR FLUORESCENT LABELS; PARACYCLOPHANE CHROMOPHORES; SOLVENT ENVIRONMENT; TOLUNE;

BIOSENSORS; CHROMOPHORES; ELECTRONIC STRUCTURE; LIGHT EMITTING DIODES; OLIGOMERS; POLYMERS; QUANTUM THEORY;

ORGANIC SOLVENTS;

EID: 20544475842     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.1878732     Document Type: Article

References (74)

1. (a) M. A. Fox, Acc. Chem. Res. 0001-4842 32, 201 (1999);
2. (b) G. D. Scholes, J. Phys. Chem. 100, 18731 (1996).
3. D. T. McQuade, A. E. Pullen, and T. M. Swagert, Chem. Rev. (Washington, D.C.) 100, 2537 (2000).
4. (a) S. Canuto and M. C. Zerner, Chem. Phys. Lett. 0009-2614 157, 353 (1989);
5. (b) S. Canuto and M. Zerner, J. Am. Chem. Soc. 112, 2114 (1990).
6. (a) G. C. Bazan, W. J. Oldham, Jr., R. J. Lachicotte, S. Tretiak, V. Chernyak, and S. Mukamel, J. Am. Chem. Soc. 0002-7863 10.1021/ja973816h 120, 9188 (1998);
7. (b) S. Wang, G. C. Bazan, S. Tretiak, and S. Mukamel, J. Am. Chem. Soc. 0002-7863 10.1021/ja991611y 122, 1289 (2000);
8. (c) S. Tretiak and S. Mukamel, Chem. Rev. (Washington, D.C.) 102, 3171 (2002).
9. (a) Y. Morisaki and Y. Chujo, Macromolecules 0024-9297 37, 4099 (2004);
10. (b) D. S. Seferos, D. A. Banach, N. A. Alcantar, J. N. Israelachvili, and G. C. Bazan, J. Org. Chem. 0022-3263 10.1021/jo035664g 69, 1110 (2004);
11. (c) J. Gierschner, H. G. Mack, D. Oelkrug, I. Waldner, and H. Rau, J. Phys. Chem. 0022-3654 108, 257 (2004);
12. (d) R. Salcedo, N. Mireles, and L. E. Sansores, J. Theor. Comput. Chem. 0219-6336 2, 171 (2003);
13. (e) L. Guyard, C. Dumas, F. Miomandre, R. Pansu, R. Renault-Meallet, and P. Audebert, New J. Chem. 1144-0546 27, 1000 (2003);
14. (f) G. P. Bartholomew and G. C. Bazan, J. Am. Chem. Soc. 0002-7863 10.1021/ja0121383 124, 5183 (2001);
15. (g) G. P. Bartholomew and G. C. Bazan, Acc. Chem. Res. 0001-4842 10.1021/ar9901568 34, 30 (2001);
16. (h) N. Verdal, J. T. Godbout, T. L. Perkins, G. P. Bartholomew, G. C. Bazan, and A. M. Kelley, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(00) 00194-9 320, 95 (2000);
17. (i) W. J. Warren, Jr., Y.-J. Miao, R. J. Lachicotte, and G. C. Bazan, J. Am. Chem. Soc. 120, 419 (1998).
18. (a) X. Zhou, A.-M. Ren, J.-K. Feng, and X.-J. Liu, J. Phys. Chem. A 1089-5639 107, 1850 (2003);
19. (b) G. P. Bartholomew, I. Ledoux, S. Mukamel, G. C. Bazan, and J. Zyss, J. Am. Chem. Soc. 0002-7863 10.1021/ja0272179 124, 13480 (2002);
20. (c) J. Zyss, I. Ledoux, S. Volkov, V. Chernyak, S. Mukamel, G. P. Bartholomew, and G. C. Bazan, J. Am. Chem. Soc. 122, 11956 (2000).
21. G. P. Bartholomew, M. Rumi, S. J. K. Pond, J. W. Perry, S. Tretiak, and G. C. Bazan, J. Am. Chem. Soc. 126, 11529 (2004).
22. (a) J. W. Hong, B. S. Gaylord, and G. C. Bazan, J. Am. Chem. Soc. 0002-7863 124, 11868 (2002);
23. (b) J. W. Hong, H. Benmansour, and G. C. Bazan, Chem.-Eur. J. 0947-6539 9, 3186 (2003);
24. (c) J. W. Hong, H. Y. Woo, B. Liu, and G. C. Bazan, J. Am. Chem. Soc. 127, 7435 (2005).
25. M. J. Frisch, G. W. Trucks, H. B. Schlegel, GAUSSIAN 03, Revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
26. (a) E. Cances, B. Mennucci, and J. Tomasi, J. Chem. Phys. 0021-9606 10.1063/1.474659 107, 3032 (1997);
27. (b) B. Mennucci, R. Cammi, and J. Tomasi, J. Chem. Phys. 109, 2798 (1998).
28. A. Masunov and S. Tretiak, J. Phys. Chem. B 108, 899 (2004).
29. C. Katan, F. Terenziani, O. Mongin, M. H. V. Werts, L. Porr̀s, T. Pons, J. Mertz, S. Tretiak, M. Blanchard-Desce, J. Phys. Chem. A 109, 3024 (2005).
30. (a) E. Runge and E. K. U. Gross, Phys. Rev. Lett. 52, 997 (1984);
31. (b) M. E. Casida, in Recent Advances in Density-Functional Methods, edited by, D. A. Chong, (World Scientific, Singapore, 1995), Vol. 3.
32. J. Fabian, L. A. Diaz, G. Seifert, and T. Niehaus, J. Mol. Struct.: THEOCHEM 594, 41 (2002).
33. D. A. McQuarrie and J. D. Simon, Physical Chemistry: A Molecular Approach (University Science Books, Sausalito, CA, 1997).
34. R. L. Martin, J. Chem. Phys. 118, 4775 (2003).
35. A. Kokalj, J. Mol. Graphics Modell. 17, 176 (1999);
36. Code available from http://www.xcrysden.org.
37. S. P. Kwasniewski, L. Claes, J. P. Francois, and M. S. Deleuze, J. Chem. Phys. 118, 7823 (2003).
38. M. Traetteberg, E. B. Frantsen, F. C. Mijlhoff, and A. Hoekstra, J. Mol. Struct. 26, 57 (1975).
39. J. A. Bouwstra, A. Schouten, and J. Kroon, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 40, 428 (1984).
40. J. Harada and K. Ogawa, J. Am. Chem. Soc. 123, 10884 (2001).
41. C. H. Choi and M. Kertesz, J. Phys. Chem. A 101, 3823 (1997).
42. B. B. Champagne, J. F. Pfanstiel, D. F. Plusquellic, D. W. Pratt, W. M. Van Herpen, and W. L. Meerts, J. Phys. Chem. 94, 6 (1990).
43. S. Tretiak, K. Igumenshchev, and V. Chernyak, Phys. Rev. B 71, 033201 (2005).
44. N. Kobko, A. Masunov, and S. Tretiak, Chem. Phys. Lett. 392, 444 (2004).
45. (a) A. Karpfen, C. H. Choi, and M. Kertesz, J. Phys. Chem. A 1089-5639 10.1021/jp971606l 101, 7426 (1997);
46. (b) J. C. Sancho-Garcia, J. L. Bredas, and J. Cornil, Chem. Phys. Lett. 0009-2614 10.1016/S0009-2614(03)01086-8 377, 63 (2003);
47. (c) J. C. Sancho-Garcia and J. Cornil, J. Chem. Phys. 121, 3096 (2004).
48. C. H. Choi, M. Kertesz, and A. Karpfen, J. Chem. Phys. 107, 6712 (1997).
49. A. Masunov and J. J. Dannenberg, J. Phys. Chem. A 103, 178 (1999).
50. V. Molina, M. Merchán, and B. O. Roos, J. Phys. Chem. 101, 3478 (1997).
51. J. Gierschner, H. G. Mack, L. Luer, and D. Oelkrug, J. Chem. Phys. 116, 8596 (2002).
52. W.-Y. Chiang and J. Laane, J. Chem. Phys. 100, 8755 (1994).
53. (a) E. Zojer, P. Buchacher, F. Wudl, J. Cornil, J. P. Calbert, J. L. Bredas, and G. Leising, J. Chem. Phys. 0021-9606 10.1063/1.1323263 113, 10002 (2000);
54. (b) I. Franco and S. Tretiak, J. Am. Chem. Soc. 126, 12130 (2004).
55. D. A. Bussian, M. A. Summers, B. Liu, G. C. Bazan, and S. K. Buratto, Chem. Phys. Lett. 388, 181 (2004).
56. (a) M. Born, Z. Phys. 0044-3328 1, 45 (1920);
57. (b) J. G. Kirkwood, J. Chem. Phys. 0021-9606 10.1063/1.1749489 2, 351 (1934);
58. (c) L. Onsager, J. Am. Chem. Soc. 58, 1486 (1936).
59. (a) D. M. Chipman, J. Chem. Phys. 0021-9606 112, 558 (2000);
60. (b) M. Cossi and V. Barone, J. Chem. Phys. 115, 4708 (2001).
61. M. A. Aguilar, J. Phys. Chem. A 105, 10393 (2001).
62. C. Adamo and V. Barone, Chem. Phys. Lett. 330, 152 (2000).
63. C. Zazzaa, L. Bencivenni, A. Grandia, and A. Aschi, J. Mol. Struct.: THEOCHEM 680, 117 (2004).
64. F. Aquilante, M. Cossi, O. Crescenzi, G. Scalmani, and V. Barone, Mol. Phys. 101, 1945 (2003).
65. F. Aquilante, V. Barone, and B. O. Roos, J. Chem. Phys. 119, 12323 (2003).
66. R. Improta, F. Santoro, C. Dietl, E. Papastathopoulos, and G. Gerber, Chem. Phys. Lett. 387, 509 (2004).
67. B. Mennucci, J. Tomasi, K. Ruud, and K. V. Mikkelsen, J. Chem. Phys. 117, 13 (2002).
68. W. G. Han, T. Q. Liu, F. Himo, A. Toutchkine, D. Bashford, K. M. Hahn, and L. Noodleman, ChemPhysChem 4, 1084 (2003).
69. T. Q. Liu, W. G. Han, F. Himo, G. M. Ullmann, D. Bashford, A. Toutchkine, K. M. Hahn, and L. Noodleman, J. Phys. Chem. A 108, 3545 (2004).
70. S. Corni, C. Cappelli, M. Del Zoppo, and J. Tomasi, J. Phys. Chem. A 107, 10261 (2003).
71. A. Masunov and T. Lazaridis, J. Am. Chem. Soc. 125, 1722 (2003).
72. S. Schneider, M. O. Schmitt, G. Brehm, M. Reiher, P. Matousek, and M. Towrie, Photochem. Photobiol. Sci. 2, 1107 (2003).
73. M. G. Mason, C. W. Tang, L. S. Hung, J. Appl. Phys. 89, 2756 (2001).
74. Y. Yuan, D. Grozea, S. Han, and Z. H. Lu, Appl. Phys. Lett. 85, 4959 (2004).