Intramolecular charge transfer with 4-fluorofluorazene and the flexible 4-fluoro-N-phenylpyrrole

Journal of Physical Chemistry A

Volumn 113, Issue 33, 2009, Pages 9304-9320

  Druzhinin, Sergey I ^a,g   Kovalenko, Sergey A ^b   Senyushkina, Tamara A ^a   Demeter, Attila ^c   Januskevicius, Regis ^d   Mayer, Peter ^e   Stalke, Dietmar ^f   Machinek, Reinhard ^f   Zachariasse, Klaas A ^a  

^a MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

^c CHEMICAL RESEARCH CENTER   (Hungary)

^d CENTER FOR PHYSICAL SCIENCES AND TECHNOLOGY   (Lithuania)

^e UNIVERSITY OF MUNICH   (Germany)

^f UNIVERSITY OF GÖTTINGEN   (Germany)

^g MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE TEMPERATURES; DECAY TIME; DICHLOROETHANE; DONOR AND ACCEPTOR; DUAL FLUORESCENCE; ETHYL CYANIDE; EXCITED STATE ABSORPTION; FEMTOSECONDS; FLUORESCENCE DECAYS; FLUORESCENCE QUANTUM YIELD; FLUORESCENCE SPECTRA; INTRA-MOLECULAR CHARGE TRANSFER; INTRAMOLECULAR CHARGE TRANSFERS; LOCALLY EXCITED; N-HEXANE; N-PROPYL; PHENYLPYRROLE; PICOSECONDS; POLAR SOLVENTS; PYRROLE GROUPS; REACTION ENTHALPIES; REACTION MECHANISM; SINGLET EXCITED STATE; SOLVENT POLARITY; TETRA-HYDROFURAN; TIME DEVELOPMENT; TWO-STATE; X-RAY CRYSTAL ANALYSIS;

ACETONITRILE; ALGEBRA; BOND LENGTH; CHARGE TRANSFER; CYANIDES; EXCITED STATES; FLUORESCENCE; HEXANE; ION EXCHANGE; MASS TRANSFER; RATE CONSTANTS; SULFUR COMPOUNDS;

SOLVENTS;

4 FLUORO N PHENYLPYRROLE; 4 FLUOROFLUORAZENE; 4-FLUORO-N-PHENYLPYRROLE; 4-FLUOROFLUORAZENE; FUSED HETEROCYCLIC RINGS; HEXANE; NITRILE; PYRROLE DERIVATIVE;

ABSORPTION; ARTICLE; CHEMISTRY; ELECTRON TRANSPORT; KINETICS; SPECTROFLUOROMETRY; TEMPERATURE; THERMODYNAMICS;

ABSORPTION; ELECTRON TRANSPORT; HETEROCYCLIC COMPOUNDS, 3-RING; HEXANES; KINETICS; NITRILES; PYRROLES; SPECTROMETRY, FLUORESCENCE; TEMPERATURE; THERMODYNAMICS;

EID: 70349201151     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp903613c     Document Type: Article

References (59)

1. Yoshihara, T.; Druzhinin, S. I.; Zachariasse, K. A. J. Am. Chem. Soc. 2004, 126, 8535.
2. Druzhinin, S. I.; Kovalenko, S. A.; Senyushkina, T. A.; Demeter, A.; Machinek, R.; Noltemeyer, M.; Zachariasse, K. A. J. Phys. Chem. A 2008, 112, 8238;
3. Erratum. J. Phys. Chem. A 2009, 113, 520.
4. Yoshihara, T.; Galievsky, V. A.; Druzhinin, S. I.; Saha, S.; Zachariasse, K. A. Photochem. Photobiol. Sci. 2003, 2, 342.
5. Yoshihara, T.; Druzhinin, S. I.; Demeter, A.; Kocher, N.; Stalke, D.; Zachariasse, K. A. J. Phys. Chem. A 2005, 109, 1497.
6. Druzhinin, S. I.; Ernsting, N. P.; Kovalenko, S. A.; Lustres, L. P.; Senyushkina, T. A.; Zachariasse, K. A. J. Phys. Chem. A 2006, 110, 2955.
7. Galievsky, V. A.; Druzhinin, S. I.; Demeter, A.; Jiang, Y.-B.; Kovalenko, S. A.; Lustres, L. P.; Venugopal, K.; Ernsting, N. P.; Alionas, X.; Noltemeyer, M.; Machinek, R.; Zachariasse, K. A. ChemPhysChem 2005, 6, 2307.
8. Mortensen, J.; Heinze, J. Angew. Chem. 1984, 96, 64.
9. 2) is the determining factor for the occurrence of an ICT reaction. A recent example of this situation is found with tricyanoanilines such as 2,4,6-tricyano-NN-dimethylaniline (TCDMA); see ref 12.
10. von der Haar, Th.; Hebecker, A.; Il'ichev, Yu. V.; Jiang, Y.-B.; Kühnle, W.; Zachariasse, K. A. Reci. Trav. Chim. Pays-Bas 1995, 114, 430.
11. Il'ichev, Yu. V.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. A 1998, 102, 5670.
12. Galievsky, V. A.; Zachariasse, K. A. Acta Phys. Pol., A 2007, 112, S-39.
13. Zachariasse, K. A.; Druzhinin, S. I.; Galievsky, V. A.; Kovalenko, S.; Senyushkina, T. A.; Mayer, P.; Noltemeyer, M.; Boggio-Pasqua, M.; Robb, M. A. J. Phys. Chem. A 2009, 113, 2693.
14. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, 1971.
15. Cogan, S.; Zilberg, S.; Haas, Y. J. Am. Chem. Soc. 2006, 128, 3335.
16. Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem. Rev. 2003, 103, 3899.
17. Lippert, E.; Lüder, W.; Boos, H. In Advances in Molecular Spectroscopy, European Conference on Molecular Spectroscopy, Bologna, Italy, 1959;
18. Mangini, A., Ed.; Pergamon Press: Oxford, U.K., 1962; p 443.
19. Lippert, E.; Lüder, W.; Moll, F.; Nägele, W.; Boos, H.; Prigge, H.; Seibold-Blankenstein, I. Angew. Chem. 1961, 73, 695.
20. Grabowski, Z. R.; Rotkiewicz, K.; Rubaszewska, W.; KirkorKaminska, E. Acta Phys. Pol. 1978, 54A, 767.
21. Rettig, W.; Wermuth, G.; Lippert, E. Ber. Bunsenges. Phys. Chem. 1979, 83, 692.
22. -/A) = -2.36 V vs SCE has been reported in ref 6.
23. Loutfy, R. O.; Loutfy, R. O. Can. J. Chem. 1976, 54, 1454.
24. Elming, N.; Clauson-Kaas, N. Acta Chem. Scand. 1952, 6, 867.
25. Bailey, A. S.; Scott, P. W.; Vandrevala, M. H. J. Chem. Soc, Perkin Trans. 1 1980, 97.
26. Druzhinin, S. I.; Kovalenko, S. A.; Senyushkina, T.; Zachariasse, K. A. J. Phys. Chem. A 2007, 111, 12878.
27. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.
28. Druzhinin, S. I.; Galievsky, V. A.; Zachariasse, K. A. J. Phys. Chem. A 2005, 109, 11213.
29. Kocher, N.; Leusser, D.; Meindl, K.; Henn, J.; Zachariasse, K. A.; Sheldrick, G. M.; Koritsanszky, T.; Stalke, D. J. Phys. Chem. A, in press.
30. von Bülow, R. Diplomarbeit (Master Thesis), University of Göttingen, 1996.
31. Schweke, D.; Abramov, S.; Haas, Y. Chem. Phys. 2007, 335, 87.
32. Cornelissen-Gude, C.; Rettig, W. J. Phys. Chem. A 1998, 102, 7754.
33. Rückert, I.; Hebecker, A.; Parusel, A. B. J.; Zachariasse, K. A. Z. Phys. Chem. 2000, 214, 1597.
34. (a) Rückert, I.; Demeter, A.; Morawski, O.; Kühnle, W.; Tauer, E.; Zachariasse, K. A. J. Phys. Chem. A 1999, 103, 1958.
35. (b) Zachariasse, K. A.; Grobys, M.; von der Haar, Th.; Hebecker, A.; Il'ichev, Yu. V.; Jiang, Y.-B.; Morawski, O.; Kühnle, W. J. Photochem. Photobiol, A 1996, 102, 59;
36. Erratum. J. Photochem. Photobiol, A 1998, 115, 259.
37. Druzhinin, S. I.; Galievsky, V. A.; Yoshihara, T.; Zachariasse, K. A. J. Phys. Chem. A 2006, 110, 12760.
38. In the subtraction procedure to separate a weak ICT emission from the main LE fluorescence band, the problem arises that the fluorescence spectrum adopted for LE is not exactly that of the LE emission, but rather that of a model compound, such as PP4M employed here, which is at best similar but certainly not identical to the real LE fluorescence band. For this reason, Φ'(ICT)/Φ(LE) ratios of 0.02 such as reported by us (ref 4) for PP in THF at 25 °C are at the limit of the possible experimental accuracy, although the value of 0.02 was obtained by analyzing a series of measurements as a function of temperature in THF, with Φ'(ICT)/Φ(LE) = 0.05 at-104 °C (ref 4).
39. Il'ichev, Yu, V.; Kühnle, W.; Zachariasse, K. A. Chem. Phys. 1996, 211, 441.
40. Suppan, P.; Ghoneim, N. Solvatochromism; The Royal Society of Chemistry: Cambridge, U.K., 1997.
41. Liptay, W. In Excited States; Lim, E. C., Ed.; Academic Press: New York, 1974, Vol.1, p 129.
42. Baumann, W.; Bischof, H.; Brittinger, J.-C.; Rettig, W.; Rotkiewicz, K. J. Photochem. Photobiol, A 1992, 64, 49.
43. Demeter, A.; Druzhinin, S.; George, M.; Haselbach, E.; Roulin, J.-L.; Zachariasse, K. A. Chem. Phys. Lett. 2000, 323, 351.
44. Zachariasse, K. A.; Druzhinin, S. I.; Bosch, W.; Machinek, R. J. Am. Chem. Soc. 2004, 126, 1705.
45. Hedestrand, G. Z. Phys. Chem. B 1929, 2, 428.
46. At -45 °C, the dielectric constants are the following: 50.2 (MeCN), 39.0 (EtCN), 35.1 (PrCN) (see ref 4).
47. Landolt-Börnstein. In Numerical Data and Functional Relationships in Science and Technology, New Series; Madelung, O., Ed.; Springer: Berlin, 1991; Vol.6, Group IV.
48. Leinhos, U.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. 1991, 95, 2013.
49. Stevens, B.; Ban, M. I. Trans. Faraday Soc. 1964, 60, 1515.
50. Birks, J. B. Photophysics of Aromatic Molecules; Wiley: London, 1970.
51. Gómez, I.; Reguero, M.; Boggio-Pasqua, M.; Robb, M. A. J. Am. Chem. Soc. 2005, 127, 7119.
52. Gómez, I.; Mercier, Y.; Reguero, M. J. Phys. Chem. A 2006, 110, 11455.
53. Conte, J. C.; Martinho, J. M. G. Chem. Phys. Lett. 1987, 134, 350.
54. Zachariasse, K. A.; Yoshihara, T.; Druzhinin, S. I. J. Phys. Chem. A 2002, 106, 6325;
55. Erratum. J. Phys. Chem. A 2002, 106, 8978.
56. Duveneck, G.; Zachariasse, K. A. J. Am. Chem. Soc. 1987, 109, 3790.
57. Williams, A. Free Energy Relationships in Organic and Bio-organic Chemistry; The Royal Society of Chemistry: Cambridge, U.K., 2003.
58. a; see Table 5.
59. -1) for PP4C. Although the ICT reaction for FPP4C/PP4C will become somewhat slower in EtCN at -45 °C, it will nevertheless remain much faster than that for the pairs FPP/PP and FPP4F/PP4F. In support of this conclusion, only ICT fluorescence is observed with FPP4C and PP4C in EtCN at -45 °C (ref 2).