Fluorescence quenching in an organic donor-acceptor dyad: A first principles study

Journal of Chemical Physics

Volumn 131, Issue 3, 2009, Pages

  Korzdorfer T ^a   Tretiak, S ^b   Kummel S ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

^b LOS ALAMOS NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY; ENERGY TRANSFER; FLUORESCENCE; LIGHT EMISSION; MOLECULAR DYNAMICS; ORGANIC SOLAR CELLS; POLYCYCLIC AROMATIC HYDROCARBONS; SOLAR CELLS;

CHARGE TRANSFER PROCESS; CONFORMATIONAL DYNAMICS; FIRST-PRINCIPLES STUDY; FLUORESCENCE QUENCHING; LIGHT EMITTING DEVICES; RESONANT ENERGY TRANSFER; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TRIPHENYL DIAMINES;

QUENCHING;

BENZIDINE DERIVATIVE; DRUG DERIVATIVE; FLUORESCENT DYE; IMIDE; PERYLENE; PERYLENE BISIMIDE; TETRAPHENYLBENZIDINE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; FLUORESCENCE; QUANTUM THEORY;

BENZIDINES; COMPUTER SIMULATION; FLUORESCENCE; FLUORESCENT DYES; IMIDES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PERYLENE; QUANTUM THEORY;

EID: 67651183978     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.3160666     Document Type: Article

References (55)

1. M. Newton, Chem. Rev. (Washington, D.C.) 0009-2665 91, 767 (1991). 10.1021/cr00005a007
2. S. Speiser, Chem. Rev. (Washington, D.C.) 0009-2665 96, 1953 (1996). 10.1021/cr941193+
3. J. -L. Bŕdas, D. Beljonne, V. Coropceanu, and J. Cornil, Chem. Rev. (Washington, D.C.) 0009-2665 104, 4971 (2004). 10.1021/cr040084k
4. V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, and J. -L. Bŕdas, Chem. Rev. (Washington, D.C.) 0009-2665 107, 926 (2007). 10.1021/cr050140x (Pubitemid 46736532)
5. I. B. Ramsteiner, A. Hartschuh, and H. Port, Chem. Phys. Lett. 0009-2614 343, 83 (2001) 10.1016/S0009-2614(01)00683-2; Molecular Switches, edited by, B. L. Feringa, (Wiley-VCH, Weinheim, 2001); M. W. Holman, P. Yan, K. -C. Ching, R. Liu, F. I. Ishak, and D. M. Adams, Chem. Phys. Lett. 0009-2614 413, 501 (2005). 10.1016/j.cplett.2005.06.128
6. Advances in Photosynthesis and Respiration, Light-Harvesting Antennas in Photosynthesis, edited by, B. R. Green, and, W. W. Parson, (Kluwer, Dordrecht, 2003), Vol. 13.
7. T. Christ, F. Kulzer, T. Weil, K. Müllen, and T. Basch́, Chem. Phys. Lett. 0009-2614 372, 878 (2003) 10.1016/S0009-2614(03)00515-3; P. Tinnefeld, K. D. Weston, T. Vosch, M. Cotlet, T. Weil, J. Hofkens, K. Müllen, F. C. de Schryver, and M. Sauer, J. Am. Chem. Soc. 0002-7863 124, 14310 (2002). 10.1021/ja027343c
8. U. Anton and K. Müllen, Macromolecules 0024-9297 26, 1248 (1993) 10.1021/ma00058a008; E. E. Neuteboom, S. C. J. Meskers, E. W. Meijer, and R. A. J. Janssen, Macromol. Chem. Phys. 1022-1352 205, 217 (2004). 10.1002/macp.200300044
9. H. Fidder, J. Knoester, and D. A. Wiersma, J. Chem. Phys. 0021-9606 95, 7880 (1991) 10.1063/1.461317; E. Lang, A. Sorokin, M. Drechsler, Y. V. Malyukin, and J. Köhler, Nano Lett. 1530-6984 5, 2635 (2005). 10.1021/nl051132z
10. W. B. Davis, W. A. Svec, M. A. Ratner, and M. R. Wasielewski, Nature (London) 0028-0836 396, 60 (1998) 10.1038/25090; C. G. Hübner, V. Ksenofontov, F. Nolde, K. Müllen, and T. Basch́, J. Chem. Phys. 0021-9606 120, 10867 (2004).
11. T. D. M. Bell, A. Stefan, S. Masuo, T. Vosch, M. Lor, M. Cotlet, J. Hofkens, S. Bernhardt, K. Müllen, M. van der Auweraer, J. W. Verhoeven, and F. C. De Schryver, ChemPhysChem 6, 942 (2005).
12. P. Bauer, H. Wietasch, S. M. Lindner, and M. Thelakkat, Chem. Mater. 0897-4756 19, 88 (2007). 10.1021/cm061747c (Pubitemid 46150875)
13. Ch. Scharf, K. Peter, P. Bauer, Ch. Jung, M. Thelakkat, and J. Köhler, Chem. Phys. 0301-0104 328, 403 (2006). 10.1016/j.chemphys.2006.07. 030
14. G. Horowitz, F. Kouki, P. Spearman, D. Fichou, C. Nogues, X. Pan, and F. Garnier, Adv. Mater. Weinheim, Ger.) 8, 242 (1996) 10.1002/adma.19960080312 0935-9648; P. R. L. Malenfant, C. D. Dimitrakopoulos, J. D. Gelorme, L. L. Kosbar, T. O. Graham, A. Curioni, and W. Andreoni, Appl. Phys. Lett. 0003-6951 80, 2517 (2002). 10.1063/1.1467706
15. C. W. Tang, Appl. Phys. Lett. 0003-6951 48, 183 (1986) 10.1063/1.96937; L. Schmidt-Mende, A. Fechtenkotter, K. Mullen, E. Moons, R. H. Friend, and J. D. MacKenzie, Science 0036-8075 293, 1119 (2001). 10.1126/science.293.5532.1119
16. V. Bulović, G. Gu, P. E. Burrows, S. R. Forrest, and M. E. Thompson, Nature (London) 0028-0836 380, 29 (1996) 10.1038/380029a0; N. Tamoto, C. Adachi, and K. Nagai, Chem. Mater. 0897-4756 9, 1077 (1997) 10.1021/cm960391+; E. Bellmann, S. E. Shaheen, R. H. Grubbs, S. R. Marder, B. Kippelen, and N. Peyghambarian, Chem. Mater. 0897-4756 11, 399 (1999) 10.1021/cm980614r; Y. Shirota, J. Mater. Chem. 0959-9428 15, 75 (2005). 10.1039/b413819h
17. K. D. Jordan and M. N. Paddon-Row, Chem. Rev. (Washington, D.C.) 0009-2665 92, 395 (1992). 10.1021/cr00011a003
18. Experimental spectra supplied by Christiane Hofmann; also see Ref..
19. B. P. Krueger, G. D. Scholes, and G. R. Fleming, J. Phys. Chem. B 1089-5647 102, 5378 (1998) 10.1021/jp9811171; D. Beljonne, J. Cornil, R. Silbey, P. Millie, and J. -L. Bŕdas, J. Chem. Phys. 0021-9606 112, 4749 (2000) 10.1063/1.481031; D. Beljonne, G. Pourtois, C. Silva, E. Hennebicq, L. M. Herz, R. H. Friend, G. D. Scholes, S. Setayesh, K. Müllen, and J. L. Bŕdas, Proc. Natl. Acad. Sci. U.S.A. 0027-8424 99, 10982 (2002) 10.1073/pnas.172390999; G. D. Scholes, Annu. Rev. Phys. Chem. 0066-426X 54, 57 (2003) 10.1146/annurev.physchem.54.011002.103746; S. Jang, M. D. Newton, and R. J. Silbey, Phys. Rev. Lett. 0031-9007 92, 218301 (2004) 10.1103/PhysRevLett.92. 218301; H. Wiesenhofer, D. Beljonne, G. D. Scholes, E. Hennebicq, J.-L. Bŕdas, and E. Zojer, Adv. Funct. Mater. 1616-301X 15, 155 (2005) 10.1002/adfm.200400108; M. E. Madjet, A. Abdurahman, and T. Renger, J. Phys. Chem. B 1089-5647 110, 17268 (2006). 10.1021/jp0615398
20. A. E. Clark, C. Qin, and A. D. Q. Li, J. Am. Chem. Soc. 0002-7863 129, 7586 (2007). 10.1021/ja0687724 (Pubitemid 46981922)
21. R. Ahlrichs, M. Bär, M. Häser, H. Horn, and C. Kölmel, Chem. Phys. Lett. 0009-2614 162, 165 (1989) 10.1016/0009-2614(89)85118-8; F. Furche and D. Rappoport, in Computational Photochemistry, edited by, M. Olivucci, (Elsevier, Amsterdam, 2005), Vol. 16, Chap..
22. M. J. Frisch, G. W. Trucks, H. B. Schlegel, Gaussian 03 (Revision D.02), Gaussian, Inc., Wallingford CT (2004).
23. O. Treutler and R. Ahlrichs, J. Chem. Phys. 0021-9606 102, 346 (1995). 10.1063/1.469408
24. S. Grimme, J. Comput. Chem. 0192-8651 25, 1463 (2004) 10.1002/jcc.20078; S. Grimme, J. Comput. Chem. 0192-8651 27, 1787 (2006). 10.1002/jcc.20495
25. P. J. Stevens, J. F. Devlin, C. F. Chabalowski, and M. J. Frisch, J. Phys. Chem. 0022-3654 98, 11623 (1994). 10.1021/j100096a001
26. A. Schäfer, H. Horn, and R. Ahlrichs, J. Chem. Phys. 0021-9606 97, 2571 (1992). 10.1063/1.463096
27. A. Klamt and G. Schüürmann, J. Chem. Soc. Perkin Trans. 2 1993, 799. 10.1039/p29930000799
28. COSMO is used in all calculations of geometries and excited state energies. Unless otherwise noted we used a permittivity of =2.0 for all calculations. This corresponds to the permittivity of dodecane and is close to the permittivity of toluene (=2.4) at room temperature, both being solvents primarily used in the experiment of Ref.. Note, that in the calculation of the natural transition orbitals (however, not in the energies) solution effects are neglected.
29. R. L. Martin, J. Chem. Phys. 0021-9606 118, 4775 (2003). 10.1063/1.1558471
30. P. Ren and J. W. Ponder, J. Phys. Chem. B 1089-5647 107, 5933 (2003). 10.1021/jp027815+
31. N. L. Allinger, Y. H. Yuh, and J. -H. Lii, J. Am. Chem. Soc. 0002-7863 111, 8551 (1989) 10.1021/ja00205a001; J. -H. Lii and N. L. Allinger, J. Am. Chem. Soc. 0002-7863 111, 8566 (1989) 10.1021/ja00205a002; J. -H. Lii and N. L. Allinger, J. Am. Chem. Soc. 0002-7863 111, 8576 (1989). 10.1021/ja00205a003
32. J. R. Hill, VIEWMOL Program, Version 2.4, 2003.
33. W. Humphrey, A. Dalke, and K. Schulten, J. Mol. Graphics 0263-7855 14, 33 (1996). 10.1016/0263-7855(96)00018-5 (Pubitemid 26152973)
34. For all calculations on PTCDI, we checked the influence of the sidechains on the geometrical structure, the KS-eigenvalues and TDDFT excitation spectra in the relevant energetical range.
35. M. Malagoli and J. -L. Bŕdas, Chem. Phys. Lett. 0009-2614 327, 13 (2000). 10.1016/S0009-2614(00)00757-0
36. F. Pichierri, J. Mol. Struct. 0022-2860 686, 57 (2004). 10.1016/j.theochem.2004.08.012
37. J. F. Janak, Phys. Rev. B 0163-1829 18, 7165 (1978). 10.1103/PhysRevB.18. 7165
38. M. Levy, J. P. Perdew, and V. Sahni, Phys. Rev. A 1050-2947 30, 2745 (1984). 10.1103/PhysRevA.30.2745
39. M. Levy, Phys. Rev. A 1050-2947 52, R4313 (1995). 10.1103/PhysRevA.52. R4313
40. A. Görling, Phys. Rev. A 1050-2947 54, 3912 (1996). 10.1103/PhysRevA.54.3912
41. U. Salzner, J. B. Lagowski, P. G. Pickup, and R. A. Poirier, J. Comput. Chem. 0192-8651 18, 1943 (1997). 10.1002/(SICI)1096-987X(19971130)18:15<1943: :AID-JCC9>3.0.CO;2-O
42. For a detailed discussion of the band-gap problem for hybrids, see, e.g., S. Kümmel and L. Kronik, Rev. Mod. Phys. 0034-6861 80, 3 (2008). 10.1103/RevModPhys.80.3
43. Experimental excitation energies taken at the maxima of the absorption spectrum.
44. Th. Förster, Ann. Phys. 0003-3804 437, 55 (1948). 10.1002/andp.19484370105
45. Reoptimization of the DBA2 geometry using a dispersion correction as provided in Ref. 23 leads to a collapse of the bridge with a final D-A distance of approximately 5 Å. Note that this corresponds to the mean D-A distance found in the MD and thus supports the MD results. Note further that the dispersion correction has only minor effects on the geometry of DBA1 and DBA3.
46. R. J. Magyar and S. Tretiak, J. Chem. Theory Comput. 1549-9618 3, 976 (2007). 10.1021/ct600282k
47. C. Wu, S. Tretiak, and V. Y. Chernyak, Chem. Phys. Lett. 0009-2614 433, 305 (2007) 10.1016/j.cplett.2006.11.069; E. Badaeva and S. Tretiak, Chem. Phys. Lett. 0009-2614 450, 322 (2008). 10.1016/j.cplett.2007.10.108
48. M. E. Casida, F. Gutierrez, J. Guan, F. -X. Gadea, D. Salahub, and J. -P. Daudey, J. Chem. Phys. 0021-9606 113, 7062 (2000) 10.1063/1.1313558; D. Tozer, J. Chem. Phys. 0021-9606 119, 12697 (2003) 10.1063/1.1633756; N. T. Maitra, J. Chem. Phys. 0021-9606 122, 234104 (2005) 10.1063/1.1924599; J. Neugebauer, O. Gritsenko, and E. J. Baerends, J. Chem. Phys. 0021-9606 124, 214102 (2006). 10.1063/1.2197829
49. We calculated the excitation spectrum of DBA2 using time-dependent Hartree-Fock (TDHF) and functionals using 50% (BHandHLYP), 20% (B3LYP), and no Hartree-Fock exchange (PBE). While the HOMO-LUMO excitations of D and A varied by up to 0.4 eV, the charge-transfer excitations where generally shifted by several eV.
50. A. Dreuw and M. Head-Gordon, Chem. Rev. (Washington, D.C.) 0009-2665 105, 4009 (2005). 10.1021/cr0505627
51. We calculated the excitation spectrum of DBA3 using TDHF, BHandHLYP, B3LYP, and PBE. The shift of all relevant excitations varied up to 0.4 eV. Thus the long-range charge transfer problem of commonly used functionals does not affect our results on DBA3.
52. C. Hofmann and J. Köhler, private communication (2009).
53. R. A. Marcus, J. Chem. Phys. 0021-9606 24, 966 (1956) 10.1063/1.1742723; R. A. Marcus, Rev. Mod. Phys. 0034-6861 65, 599 (1993). 10.1103/RevModPhys.65. 599
54. G. Pourtois, D. Beljonne, J. Cornil, M. A. Ratner, and J. -L. Bŕdas, J. Am. Chem. Soc. 0002-7863 124, 4436 (2002) 10.1021/ja017150+; V. Lemaur, M. Steel, D. Beljonne, J. -L. Bŕdas, and J. Cornil, J. Am. Chem. Soc. 0002-7863 127, 6077 (2005). 10.1021/ja042390l
55. T. Kawatsu, V. Coropceanu, A. Ye, and J. -L. Bŕdas, J. Phys. Chem. C 1932-7447 112, 3429 (2008). 10.1021/jp711186j
56. Q. Wu and T. van Voorhis, J. Chem. Phys. 0021-9606 125, 164105 (2006). 10.1063/1.2360263 (Pubitemid 44658343)