Intramolecular charge transfer in dual fluorescent 4-(dialkylamino)benzonitriles. Reaction efficiency enhancement by increasing the size of the amino and benzonitrile subunits by alkyl substituants

Journal of Physical Chemistry A

Volumn 102, Issue 28, 1998, Pages 5670-5680

  Il'ichev, Yurii V ^a   Kühnle, Wolfgang ^a   Zachariasse, Klaas A ^a  

^a MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001478391     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp980426o     Document Type: Article

References (67)

1. (a) Grabowski, Z. R.; Rotkiewicz, K.; Rubaszewska, W.; Kirkor-Kaminska, E. Acta Phys. Pol. 1978, A54, 767.
2. (b) Grabowski, Z.; Rotkiewicz, K.; Siemiarczuk, A.; Cowley, D. J.; Baumann, W. Nouv. J. Chim. 1979, 3, 443.
3. (c) Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971.
4. (d) Lippert, E.; Rettig, W.; Bonac̈ić-Koutecký, V.; Heisel, F.; Miehé, J. A. Adv. Chem. Phys. 1987, 68, 1.
5. Leinhos, U.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. 1991, 95, 2013.
6. (a) Lippert, E.; Lüder, W.; Boos H. In Advances in Molecular Spectroscopy; European Conference on Molecular Spectroscopy, Bologna, Italy, 1959; Mangini, A., Ed.; Pergamon: Oxford, 1962; p 443.
7. (b) Lippert, E.; Lüder, W.; Moll, F.; Nagele, H.; Boos H.; Prigge, H.; Siebold-Blankenstein, I. Angew. Chem. 1961, 73, 695.
8. (c) Lippert, E. In Luminescence of Organic and Inorganic Materials; Kallmann, H. P., Spruch, G. M., Eds.; Wiley: New York, 1962; p 271.
9. (d) Lippert, E. In Organic Molecular Photophysics; Birks, J., Ed.; Wiley: London, 1975; Vol. 2, p 1.
10. References to models for the dual fluorescence of DMABN reported in the literature are given in ref 2. The recent RICT model of Sobolewski and Domcke, introduced on the basis of theoretical calculations, is discussed in ref 42, where it is reported that an experimental verification of the predictions of this model could not be obtained.
11. von der Haar, Th.; Hebecker, A.; Il'ichev, Y.; Jiang, Y.-B.; Kühnle, W.; Zachariasse, K. A. Recl. Trav. Chim. Pays-Bas. 1995, 114, 430.
12. (a) 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: Chem. 1996, 102, 59.
13. (b) von der Haar, Th.; Hebecker, A.; Il'ichev, Yu. V.; Kühnle, W.; Zachariasse, K. A. In Fast Elementary Processes in Chemical and Biological Systems, Lille, France, 1995, AIP Conf. Proc. 1996, 364, 295.
14. Zachariasse, K. A.; Grobys, M.; von der Haar, Th.; Hebecker, A.; Il'ichev, Yu. V.; Morawski, O.; Rückert, I.; Kühnle, W. J. Photochem. Photobiol. A: Chem. 1997, 105, 373.
15. Zachariasse, K. A.; von der Haar, Th.; Hebecker, A.; Leinhos, U.; Kühnle, W. Pure Appl. Chem. 1993, 65, 1745.
16. (a) Zachariasse, K. A.; von der Haar, Th.; Leinhos, U.; Kühnle, W. J. Inf. Rec. Mats. 1994, 21, 501.
17. (b) Zachariasse, K. A.; Grobys, M.; von der Haar, Th.; Hebecker, A.; Il'ichev, Yu. V.; Kühnle, W.; Morawski, O. J. Inf. Recording 1996, 22, 553.
18. Schuddeboom, W.; Jonker, S. A.; Warman, J. M.; Leinhos, U.; Kühnle, W.; Zachariasse. K. A. J. Phys. Chem. 1992, 96, 10809.
19. Baumann, W.; Bischof, H.; Fröhling, J.-C.; Brittinger, C.; Rettig, W.; Rotkiewicz, K. J. Photochem. Photobiol. A: Chem. 1992, 64, 49.
20. 10
21. Leinhos, U. Ph.D. Thesis, University Göttingen, Germany, 1991.
22. Von der Haar, Th.; Il'ichev, Yu. V.; Zachariasse, K. A., unpublished results.
23. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991.
24. Zachariasse, K. A.; Duveneck, G.; Busse, R. J. Am. Chem. Soc. 1984, 106, 1045.
25. Striker, G. In Deconvolution and Reconvolution of Analytical Signals; Bouchy. M., Ed.; University Press: Nancy, France, 1982; p 329.
26. Zachariasse, K. A.; Kühnle, W.; Leinhos, U.; Reynders, P.; Striker, G. J. Phys. Chem. 1991, 95, 5476.
27. The maximum in the plot of ln(Φ′(CT)/Φ(LE)) versus 1000/T (K) occurs at much lower temperatures for MDB and DMABN than for their derivatives EDB/PrDB and DEABN/DPrABN: see Figure 4.
28. d, or a combination of both.
29. (a) Grabowski, Z. R.; Dobkowski, J. Pure Appl. Chem. 1983, 55, 245.
30. (b) Dobkowski, J.; Herbich, J.; Waluk, J.; Koput, J.; Kühnle, W. J. Lumin. 1989, 44, 149.
31. (c) Dobkowski, J.; Grabowski, Z. R.; Jasny, J.; Zielinski, Z. Acta Phys. Polon. 1995, 88A, 455.
32. In 4-(dimethylamino)-4′-cyano-stilbene (DCS), different suggestions have been made to partition the molecule in D and A subunits. The dimethylamino as well as the dimethylamino groups were considered as the electron donor in discussions based on the TICT model (see ref 23 and the literature cited there).
33. Il'ichev, Yu. V.; Kühnle, W.; Zachariasse, K. A. Chem. Phys. 1996, 211, 441.
34. (a) Weller, A. In The Exciplex, Gordon, M., Ware, W. R., Eds.; Academic: New York, 1975; p 23.
35. (b) Beens, H.; Weller, A. Acta Phys. Polon. 1968, 34, 593.
36. (a) Weller, A. Z. Phys. Chem. 1982, 133, 93.
37. (b) Weller, A. Z. Phys. Chem. 1982, 130, 129.
38. (a) Lindsay Smith, J. R.; Masheder, D. J. Chem. Soc., Perkin Trans. 2 1977, 47.
39. (b) Mann, C. K. Anal. Chem. 1964, 36, 2424.
40. max(CT) and the redox potentials of the A and D subunits in the aminobenzonitriles would exist (see text).
41. max(CT) and the redox potentials of the A and D subunits in the aminobenzonitriles would exist (see text).
42. (a) The reduction potentials of anthracene (-1.95 V versus SCE) and ferrocene (0.45 V versus SCE, 0.57 V versus Ag/AgCl, saturated in acetonitrile) were measured as standards in the same set of experiments; Fries, J.; Seidel C., unpublished results.
43. (b) Seidel, C. Ph.D. Thesis, University Heidelberg, Germany, 1992.
44. (a) Zachariasse, K. A. Ph.D. Thesis, Free University, Amsterdam, The Netherlands, 1972.
45. (b) Zachariasse, K. A. In the Exciplex: Gordon, M., Ware, W. R., Eds.; Academic: New York, 1975; p 275.
46. Stevens, B.; Ban, M. I. Trans. Faraday Soc. 1964, 60, 1515.
47. Birks, J. B. Photophysics of Aromatic Molecules; Wiley; London, 1970.
48. (a) Zachariasse, K. A.; Kühnle, W.; Weller, A. Chem. Phys. Lett. 1978, 59, 375.
49. (b) Zachariasse, K. A. Trends Photochem. Photobiol. 1994, 3, 211.
50. 14
51. (a) Landolt-Börnstein, Zahlenwerte und Funktionen, Bd II/6, Elektrische Eigenschaften I, 6th edition; Hellwege, K. H., Hellwege, A. M., Eds.; Springer: Berlin, 1959.
52. (b) Timmermans, J. Physico-Chemical Constants of Pure Organic Compounds, Vol. II; Elsevier: New York, 1965.
53. d.
54. 2
55. 2,40 The possible influence of dielectric solvent relaxation on the excited state behavior of DRABN and RDB in toluene will be discussed separately.
56. Zachariasse, K. A.; Busse, R.; Duveneck, G.; Kühnle, W. J. Photochem. 1985, 28, 237.
57. Whiffen, D. H.; Thompson, H. W. Faraday Discuss. Chem. Soc. 1946, 42A, 122.
58. 2 fits are still obtained. This reduction in fit quality may indicate the onset of triple exponential decays for DMABN in this temperature region.
59. Zachariasse, K. A.; Grobys, M.; Tauer, E. Chem. Phys. Lett. 1997, 274, 372.
60. f, which is somewhat smaller than the factor of 1.3 observed for both MABN and MHDB.
61. Van der Auweraer, M.; Grabowski, Z.; Rettig, W. J. Phys. Chem. 1991, 95, 2083.
62. Hicks, J.; Vandersall, M.; Babarogic, Z.; Eisenthal, K. B. Chem. Phys. Lett. 1985, 116, 18.
63. 49
64. Heine, A.; Herbst-Irmer, R.; Stalke. D.; Zachariasse, K. A. Acta Crystallogr. 1994, B50, 363.
65. von Bülow, R.; Stalke, D.; Zachariasse, K. A., unpublised results.
66. (a) Ikemoto, I.; Katagiri, G.; Nishimura, S.; Yakushi, K.; Kuroda, H. Acta Crystallogr. 1979, B35, 2264.
67. (b) De Boer, J. L.; Vos, A. Acta Crystallogr. 1972, B28, 835.