The effect of oxidation on the structure of styryl-substituted sexithiophenes: A resonance Raman spectroscopy and density functional theory study

Journal of Chemical Physics

Volumn 124, Issue 16, 2006, Pages

  Clarke, Tracey M ^a   Gordon, Keith C ^a   Officer, David L ^b   Grant, Daina K ^b,c  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b MASSEY UNIVERSITY   (New Zealand)

^c THE NEW ZEALAND INSTITUTE FOR PLANT AND FOOD RESEARCH LIMITED   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; ELECTROCHEMISTRY; MOLECULAR DYNAMICS; OXIDATION; PROBABILITY DENSITY FUNCTION; RAMAN SPECTROSCOPY;

ELECTRON DELOCALIZATION; INTERMOLECULAR INTERACTIONS; RADICAL CATIONS; SEXITHIOPHENES;

ELECTRONIC STRUCTURE;

EID: 34547236789     PISSN: 00219606     EISSN: None     Source Type: Journal    
DOI: 10.1063/1.2185095     Document Type: Article

References (39)

1. A. Pron and P. Rannou, Prog. Polym. Sci. 27, 135 (2001); W. A. Gazotti, A. F. Nogueira, E. M. Girotto, L. Micaroni, M. Martini, S. das Neves, and M. A. De Paol, Handbook of Advanced Electronic and Photonic Materials and Devices (Academic Press, San Diego, 2001), Vol. 10, p. 53.
2. A. Pron and P. Rannou, Prog. Polym. Sci. 27, 135 (2001); W. A. Gazotti, A. F. Nogueira, E. M. Girotto, L. Micaroni, M. Martini, S. das Neves, and M. A. De Paol, Handbook of Advanced Electronic and Photonic Materials and Devices (Academic Press, San Diego, 2001), Vol. 10, p. 53.
3. J. Casado, H. E. Katz, V. Hernandez, and J. T. Lopez Navarrete, J. Phys. Chem. B 106, 2488 (2002).
4. V. Hernandez, J. Casado, F. J. Ramirez, G. Zotti, S. Hotta, and J. T. L. Navarrete, J. Chem. Phys. 104, 9271 (1996).
5. J. Casado, L. L. Miller, K. R. Mann, T. M. Pappenfus, Y. Kanemitsu, E. Orti, P. M. Viruela, R. Pou-Amerigo, V. Hernandez, and J. T. Lopez Navarrete, J. Phys. Chem. B 106, 3872 (2002).
6. F. Garnier, G. Horowitz, X. Peng, and D. Fichou, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19900021207 2, 592 (1990); G. Horowitz, F. Garnier, A. Yassar, R. Hajlaoui, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19960080109 8, 52 (1996); F. Garnier, Chem. Phys. 0301-0104 10.1016/S0301-0104(97)00308-X 227, 253 (1998); D. Fichou, P. Demanze, G. Horowitz, R. Hajlaoui, M. Constant, and F. Garnier, Synth. Met. 0379-6779 10.1016/S0379-6779(97)80253-6 85, 1309 (1997); R. Hajlaoui, G. Horowitz, F. Garnier, A. Arce-Brouchet, L. Laigre, A. El Kassmi, F. Demanze, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 9, 389 (1997).
7. F. Garnier, G. Horowitz, X. Peng, and D. Fichou, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19900021207 2, 592 (1990); G. Horowitz, F. Garnier, A. Yassar, R. Hajlaoui, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19960080109 8, 52 (1996); F. Garnier, Chem. Phys. 0301-0104 10.1016/S0301-0104(97)00308-X 227, 253 (1998); D. Fichou, P. Demanze, G. Horowitz, R. Hajlaoui, M. Constant, and F. Garnier, Synth. Met. 0379-6779 10.1016/S0379-6779(97)80253-6 85, 1309 (1997); R. Hajlaoui, G. Horowitz, F. Garnier, A. Arce-Brouchet, L. Laigre, A. El Kassmi, F. Demanze, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 9, 389 (1997).
8. F. Garnier, G. Horowitz, X. Peng, and D. Fichou, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19900021207 2, 592 (1990); G. Horowitz, F. Garnier, A. Yassar, R. Hajlaoui, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19960080109 8, 52 (1996); F. Garnier, Chem. Phys. 0301-0104 10.1016/S0301-0104(97)00308-X 227, 253 (1998); D. Fichou, P. Demanze, G. Horowitz, R. Hajlaoui, M. Constant, and F. Garnier, Synth. Met. 0379-6779 10.1016/S0379-6779(97)80253-6 85, 1309 (1997); R. Hajlaoui, G. Horowitz, F. Garnier, A. Arce-Brouchet, L. Laigre, A. El Kassmi, F. Demanze, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 9, 389 (1997).
9. F. Garnier, G. Horowitz, X. Peng, and D. Fichou, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19900021207 2, 592 (1990); G. Horowitz, F. Garnier, A. Yassar, R. Hajlaoui, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19960080109 8, 52 (1996); F. Garnier, Chem. Phys. 0301-0104 10.1016/S0301-0104(97)00308-X 227, 253 (1998); D. Fichou, P. Demanze, G. Horowitz, R. Hajlaoui, M. Constant, and F. Garnier, Synth. Met. 0379-6779 10.1016/S0379-6779(97)80253-6 85, 1309 (1997); R. Hajlaoui, G. Horowitz, F. Garnier, A. Arce-Brouchet, L. Laigre, A. El Kassmi, F. Demanze, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 9, 389 (1997).
10. F. Garnier, G. Horowitz, X. Peng, and D. Fichou, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19900021207 2, 592 (1990); G. Horowitz, F. Garnier, A. Yassar, R. Hajlaoui, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 0935-9648 10.1002/adma.19960080109 8, 52 (1996); F. Garnier, Chem. Phys. 0301-0104 10.1016/S0301-0104(97)00308-X 227, 253 (1998); D. Fichou, P. Demanze, G. Horowitz, R. Hajlaoui, M. Constant, and F. Garnier, Synth. Met. 0379-6779 10.1016/S0379-6779(97)80253-6 85, 1309 (1997); R. Hajlaoui, G. Horowitz, F. Garnier, A. Arce-Brouchet, L. Laigre, A. El Kassmi, F. Demanze, and F. Kouki, Adv. Mater. (Weinheim, Ger.) 9, 389 (1997).
11. Y. Furukawa, J. Phys. Chem. 100, 15644 (1996).
12. J. Casado, V. Hernandez, S. Hotta, and J. T. Lopez Navarrete, J. Chem. Phys. 109, 10419 (1998).
13. J. Casado, L. L. Miller, K. R. Mann, T. M. Pappenfus, V. Hernandez, and J. T. Lopez Navarrete, J. Phys. Chem. B 106, 3597 (2002).
14. J. Cornil, D. Beljonne, and J. L. Bredas, J. Chem. Phys. 103, 842 (1995).
15. C. Ehrendorfer and A. Karpfen, J. Phys. Chem. 98, 7492 (1994).
16. V. Hernandez, J. Casado, and J. T. Lopez Navarrete, J. Mol. Struct. 521, 249 (2000).
17. C. Moreno Castro, M. C. Ruiz Delgado, V. Hernandez, S. Hotta, J. Casado, and J. T. Lopez Navarrete, J. Chem. Phys. 116, 10419 (2002).
18. V. Hernandez, J. Casado, F. Effenberger, and J. T. Lopez Navarrete, J. Chem. Phys. 112, 5105 (2000).
19. J. Casado, J. J. Maraver Puig, V. Hernandez, G. Zotti, and J. T. Lopez Navarrete, J. Phys. Chem. A 1089-5639 104, 10656 (2000); V. Hernandez, J. Casado, Y. Kanemitsu, and J. T. Lopez Navarrete, J. Chem. Phys. 0021-9606 10.1063/1.478596 110, 6907 (1999); J. Casado, V. Hernandez, Y. Kanemitsu, and J. T. L. Navarrete, J. Raman Spectrosc. 31, 565 (2000).
20. J. Casado, J. J. Maraver Puig, V. Hernandez, G. Zotti, and J. T. Lopez Navarrete, J. Phys. Chem. A 1089-5639 104, 10656 (2000); V. Hernandez, J. Casado, Y. Kanemitsu, and J. T. Lopez Navarrete, J. Chem. Phys. 0021-9606 10.1063/1.478596 110, 6907 (1999); J. Casado, V. Hernandez, Y. Kanemitsu, and J. T. L. Navarrete, J. Raman Spectrosc. 31, 565 (2000).
21. J. Casado, J. J. Maraver Puig, V. Hernandez, G. Zotti, and J. T. Lopez Navarrete, J. Phys. Chem. A 1089-5639 104, 10656 (2000); V. Hernandez, J. Casado, Y. Kanemitsu, and J. T. Lopez Navarrete, J. Chem. Phys. 0021-9606 10.1063/1.478596 110, 6907 (1999); J. Casado, V. Hernandez, Y. Kanemitsu, and J. T. L. Navarrete, J. Raman Spectrosc. 31, 565 (2000).
22. J. Casado, S. Hotta, V. Hernandez, and J. T. Lopez Navarrete, J. Phys. Chem. A 103, 816 (1999).
23. J. Casado, V. Hernandez, S. Hotta, and J. T. Lopez Navarrete, Adv. Mater. (Weinheim, Ger.) 10, 1458 (1998).
24. T. M. Clarke, K. C. Gordon, D. L. Officer, S. B. Hall, G. E. Collis, and A. K. Burrell, J. Phys. Chem. A 107, 11505 (2003).
25. T. M. Clarke, K. C. Gordon, D. L. Officer, and D. K. Grant, J. Phys. Chem. A 109, 1961 (2005).
26. D. K. Grant, K. W. Jolley, D. L. Officer, K. C. Gordon, and T. M. Clarke, Org. Biomol. Chem. 3, 2008 (2005).
27. G. E. Collis, A. K. Burrell, S. M. Scott, and D. L. Officer, J. Org. Chem. 68, 8974 (2003).
28. S. L. Howell and K. C. Gordon, J. Phys. Chem. A 108, 2536 (2004).
29. G. W. T. M. J. Frisch, H. B. Schlegel, G. E. Scuseria, GAUSSIAN 03, Gaussian, Inc., Pittsburgh, PA, 2003.
30. A. P. Scott and L. Radom, J. Phys. Chem. 100, 16502 (1996).
31. J. Casado, H. E. Katz, V. Hernandez, and J. T. Lopez Navarrete, Vib. Spectrosc. 30, 175 (2002).
32. See EPAPS Document No. E-JCPSA6-124-507613 for the bond length alternation and change in bond length diagrams for the VI system (Fig. 1S), the theoretical and experimental Raman spectra of III and V (Fig. 2S), the eigenvectors of particular vibrational modes of neutral I2 (Fig. 3S), the experimental solution spectra of oxidized VI (Fig. 4S), calculated Raman spectra of VI+ and VI2+ (Fig. 5S), the neutral and oxidized solution state and solid state Raman spectra of VII (Fig. 6S), and the eigenvectors of particular vibrational modes of (I) 2 2+ (Fig. 7S). This document can be reached via a direct link in the online article's HTML reference section or via the EPAPS homepage (http://www.aip.org/pubservs/epaps.html).
33. T. Nishinaga, A. Wakamiya, D. Yamazaki, and K. Komatsu, J. Am. Chem. Soc. 126, 3163 (2004).
34. E. Agosti, M. Rivola, V. Hernandez, M. Del Zoppo, and G. Zerbi, Synth. Met. 100, 101 (1999).
35. N. Yokonuma, Y. Furukawa, M. Tasumi, M. Kuroda, and J. Nakayama, Chem. Phys. Lett. 255, 431 (1996).
36. J. Casado, M. C. Ruiz Delgado, Y. Shirota, V. Hernandez, and J. T. Lopez Navarrete, J. Phys. Chem. B 1089-5647 10.1021/jp022484m 107, 2637 (2003); J. Casado, V. Hernandez, S. Hotta, and J. T. Lopez Navarrete, Synth. Met. 119, 305 (2001).
37. J. Casado, M. C. Ruiz Delgado, Y. Shirota, V. Hernandez, and J. T. Lopez Navarrete, J. Phys. Chem. B 1089-5647 10.1021/jp022484m 107, 2637 (2003); J. Casado, V. Hernandez, S. Hotta, and J. T. Lopez Navarrete, Synth. Met. 119, 305 (2001).
38. G. Zerbi, B. Chierichetti, and O. Ingaenas, J. Chem. Phys. 94, 4646 (1991).
39. D. D. Graf, R. G. Duan, J. P. Campbell, L. L. Miller, and K. R. Mann, J. Am. Chem. Soc. 119, 5888 (1997).