Effect of fluorination on the electronic structure and optical excitations of π-conjugated molecules

Journal of Chemical Physics

Volumn 126, Issue 11, 2007, Pages

  Medina, Begoña Milián ^a   Beljonne, David ^a   Egelhaaf, Hans Joachim ^b,c   Gierschner, Johannes ^a,c  

^a UNIVERSITY OF MONS   (Belgium)

^b JOHANNES KEPLER UNIVERSITY LINZ   (Austria)

^c UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED POLYMERS; DENSITY FUNCTIONAL THEORY; ELECTRONEGATIVITY; FLUORINE COMPOUNDS; MOLECULAR STRUCTURE; SUBSTITUTION REACTIONS;

FLUORINE SUBSTITUTION; MOLECULAR ORBITALS (MO); OPTICAL GAPS;

ELECTRONIC STRUCTURE;

EID: 34047118206     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.2713096     Document Type: Article

References (49)

1. R. D. Scurlock, B. Wang, P. R. Ogilby, J. R. Sheats, and R. L. Clough, J. Am. Chem. Soc. 117, 10194 (1995);
2. M. Yan, L. J. Rothberg, F. Papadimitrakopoulos, M. E. Galvin, and T. M. Miller, Phys. Rev. Lett. 73, 744 (1994);
3. S. Holdcroft, Macromolecules 24, 4834 (1991);
4. L. Lüer, H.-J. Egelhaaf, D. Oelkrug, G. Cerullo, G. Lanzani, B.-H. Huisman, and D. deLeeuw, Org. Electron. 5, 83 (2004).
5. D. J. Crouch, P. J. Skabara, M. Heeney, I. McCulloch, S. J. Coles, and M. B. Hurstshouse, Chem. Commun. (Cambridge) 2005, 1465.
6. R. M. Gurge, A. M. Sarker, P. M. Lahti, B. Hu, and F. E. Karasz, Macromolecules 30, 8286 (1997);
7. A. Raya and M. A. Mora, Polymer 45, 6391 (2004).
8. Y. Kim and T. M. Swager, Chem. Commun. (Cambridge) 2005, 372;
9. C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J. L. Brédas, P. C. Ewbank, and K. R. Mann, Chem. Mater. 16, 4463 (2004).
10. U. Salzner, Curr. Org. Chem. 8, 569 (2004).
11. S. B. Heidenhain, Y. Sakamoto, T. Suzuki, A. Miura, H. Fujikawa, T. Mori, and Y. Taga, J. Am. Chem. Soc. 122, 10240 (2000);
12. N. Koch, A. Vollmer, S. Duhm, Y. Sakamoto, and T. Suzuki, Adv. Mater. (Weinheim, Ger.) 19, 112 (2007).
13. Y. Sakamoto, T. Suzuki, M. Kobayashi, Y. Gao, Y. Fukai, Y. Inoue, F. Sato, and S. Tokito, J. Am. Chem. Soc. 126, 8138 (2004).
14. Y. Sakamoto, S. Komatsu, and T. Suzuki, J. Am. Chem. Soc. 123, 4643 (2001);
15. Synth. Met. 133-134, 361 (2003).
16. A. Facchetti, M. H. Yoon, C. L. Stern, H. E. Katz, and T. J. Marks, Angew. Chem., Int. Ed. 42, 3900 (2003).
17. D. M. Cho, S. R. Parkin, and M. D. Watson, Org. Lett. 7, 1067 (2005).
18. S. W. Watt, C. Dai, A. J. Scott, J. M. Burke, R. Ll. Thomas, J. C. Collings, C. Viney, W. Clegg, and T. B. Marder, Angew. Chem., Int. Ed. 43, 3061 (2004).
19. K. Reichenbächer, H. I. Süs, and J. Hulliger, Chem. Soc. Rev. 34, 22 (2005).
20. G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, and R. H. Grubbs, J. Am. Chem. Soc. 120, 3641 (1998).
21. J. Gierschner, M. Ehni, H.-J. Egelhaaf, B. Milián Medina, D. Beljonne, H. Benmansour, and G. C. Bazan, J. Chem. Phys. 123, 144914 (2005).
22. G. P. Bartholomew, X. Bu, and G. C. Bazan, Chem. Mater. 12, 2311 (2000);
23. V. Marcon and G. Raos, J. Phys. Chem. B 108, 18053 (2004);
24. M. D. Curtis, J. Cao, and J. W. Kampf, J. Am. Chem. Soc. 126, 4318 (2004).
25. M. H. Yoon, A. Fachetti, C. E. Stern, and T. J. Marks, J. Am. Chem. Soc. 128, 5792 (2006).
26. M. L. Renak, G. P. Bartholomew, S. Wang, P. J. Ricatto, R. J. Lachicotte, and G. C. Bazan, J. Am. Chem. Soc. 121, 7787 (1999).
27. M. Z. Zgierski, T. Fujiwara, and E. C. Lim, J. Chem. Phys. 122, 144312 (2005);
28. J. Bastide, D. Hall, E. Heilbronner, J. P. Maier, and R. G. Plevey, J. Electron Spectrosc. Relat. Phenom. 16, 205 (1979).
29. Y. Yamaguchi, J. Chem. Phys. 122, 184702 (2005).
30. P. Audebert, F. Miomandre, S. G. Di Magno, V. V. Smirnov, and P. Hapiot, Chem. Mater. 12, 2025 (2000).
31. R. Malavé Osuna, R. Ponce Ortiz, M. C. Ruiz Delgado, Y. Sakamoto, T. Suzuki, V. Hernandez, and J. T. López Navarrete, J. Phys. Chem. B 109, 20737 (2005).
32. H. Sponer, J. Chem. Phys. 22, 234 (1954).
33. S. V. Shevyakov, H. Li, R. Muthyala, A. E. Asato, J. C. Croney, D. M. Jameson, and R. S. H. Liu, J. Phys. Chem. A 107, 3295 (2003).
34. B. Strehmel, A. M. Sarker, J. H. Malpert, V. Strehmel, H. Seifert, and D. C. Neckers, J. Am. Chem. Soc. 121, 1226 (1999).
35. H.-Y. Chen and I. Chao, Chem. Phys. Lett. 401, 539 (2005).
36. P. Politzer and J. W. Timberlake, J. Org. Chem. 37, 3557 (1972).
37. M. C. Zerner, in Reviews in Computational Chemistry, edited by K. W. Lipkowitz and D. B. Boyd (VCH, New York, 1994), Vol. 2, p. 313.
38. All the HF/CIS and (TD-)DFT calculations were carried out using the TURBOMOLE 5.7.1 quantum-chemical package; R. Ahlrichs, M. Bǎr, M. Häser, H. Horn, and C. Kölmel, Chem. Phys. Lett. 162, 165 (1989).
39. J. Gierschner, J. Cornil, and H.-J. Egelhaaf, Adv. Mater. (Weinheim, Ger.) 19, 173 (2007).
40. E. Heilbronner and H. Bock, The HMO-Model and its Application (VCH, GmbH, Weinheim, 1976).
41. J. N. Murrell and H. C. Longuet-Higgins, Proc. R. Soc. London 68A, 329 (1955).
42. IUPAC Compendium of Chemical Terminology, 2nd ed., edited by A. D. Mc Naught and A. Wilkinson (Royal Society of Chemistry, Cambridge, UK, 1997).
43. ζAO of fluorine.
44. The MOs have been depicted using the MOLEKEL 4.3 program by P. Flükiger, H. P. Lüthi, S. Portmann, and J. Weber, Swiss Center for Scientific Computing, Manno, Switzerland, 2002;
45. S. Portmann and H. P. Lüthi, Chimia 54, 766 (2000).
46. The comparison between HF/CIS and experimental energies was done in terms of adiabatic transition energies since vertical transition energies are largely affected by a bad description of the potential energy hypersurface of the excited state at the CIS level.
47. J. C. Sancho-García, L. Poulsen, J. Gierschner et al., Adv. Mater. (Wein-heim, Ger.) 16, 1193 (2004).
48. 1) are 0.2 in 5Ac and 8 in PF-5Ac at the B3LYP level.
49. u, respectively), we have adopted the notation H-x and L+y for simplicity.