Presence and absence of excited state intramolecular charge transfer with the six isomers of dicyano- N, N -dimethylaniline and dicyano-(N -methyl- N -isopropyl)aniline

Journal of Physical Chemistry A

Volumn 115, Issue 40, 2011, Pages 10823-10845

  Galievsky, Victor A ^a,b   Druzhinin, Sergey I ^a   Demeter, Attila ^a,c   Kovalenko, Sergey A ^d   Senyushkina, Tamara ^a   Mayer, Peter ^e   Zachariasse, Klaas A ^a  

^a MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

^b B I STEPANOV INSTITUTE OF PHYSICS   (Belarus)

^c CHEMICAL RESEARCH CENTER   (Hungary)

^d HUMBOLDT UNIVERSITY   (Germany)

^e UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

4-(DIMETHYLAMINO)BENZONITRILE; BENZONITRILES; DECAY TIME; DELAY TIME; DIMETHYLANILINE; ELECTRON DONORS; ELECTRONIC DECOUPLING; EXCITED SINGLET STATE; EXCITED STATE ABSORPTION; EXCITED-STATE INTRAMOLECULAR CHARGE TRANSFERS; FEMTOSECOND TRANSIENT ABSORPTION; FLUORESCENCE DECAYS; FLUORESCENCE QUANTUM YIELD; FLUORESCENCE SPECTRA; INTRAMOLECULAR CHARGE TRANSFERS; LOCALLY EXCITED STATE; N-HEXANE; NONCOLLINEAR; OXIDATION POTENTIALS; PICOSECONDS; POLAR SOLVENTS; REACTION ENTHALPIES; REDUCTION POTENTIAL; SMALL ENERGY; SOLVENT POLARITY; STATE BEHAVIOR; TETRA-HYDROFURAN; TRIMETHYLAMINE; TWIST ANGLES;

ACETONITRILE; ACTIVATION ENERGY; AMINATION; ANILINE; ARRHENIUS PLOTS; CHARGE TRANSFER; DECAY (ORGANIC); DIPOLE MOMENT; ELECTRON AFFINITY; FLUORESCENCE; HEXANE; ISOMERS; ORGANIC SOLVENTS; POLYMER BLENDS; QUANTUM YIELD; RATE CONSTANTS; SOLVENTS;

EXCITED STATES;

4 DIMETHYLAMINOBENZONITRILE; 4-CYANO-N,N-DIMETHYLANILINE; ACETONITRILE; ACETONITRILE DERIVATIVE; ANILINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS; TIME; X RAY CRYSTALLOGRAPHY;

ACETONITRILES; ANILINE COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; FLUORESCENCE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS; TIME FACTORS;

EID: 80053895991     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp2045614     Document Type: Article

References (67)

1. Lippert, E.; Lüder, W.; Boos, H. In Advances in Molecular Spectroscopy; European Conference on Molecular Spectroscopy, Bologna, Italy, 1959; Mangini, A., Ed.; Pergamon Press: Oxford, U.K., 1962; p 443.
2. Lippert, E.; Lüder, W.; Moll, F.; Nägele, W.; Boos, H.; Prigge, H.; Seibold-Blankenstein, I. Angew. Chem. 1961, 73, 695
3. Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971
4. Leinhos, U.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. 1991, 95, 2013
5. Ma, C.; Kwok, W. M.; Matousek, P.; Parker, A. W.; Phillips, D.; Toner, W. T.; Towrie, M. J. Phys. Chem. A 2002, 106, 3294
6. Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem. Rev. 2003, 103, 3899
7. Druzhinin, S. I.; Ernsting, N. P.; Kovalenko, S. A.; Pérez Lustres, L.; Senyushkina, T.; Zachariasse, K. A. J. Phys. Chem. A 2006, 110, 2955
8. Grabowski, Z. R.; Rotkiewicz, K.; Siemiarczuk, A.; Cowley, D. J. Nouv. J. Chim. 1979, 3, 443
9. Zachariasse, K. A.; von der Haar, Th.; Hebecker, A.; Leinhos, U.; Kühnle, W. Pure Appl. Chem. 1993, 65, 1745
10. Zachariasse, K. A.; Druzhinin, S. I.; Galievsky, V. A.; Demeter, A.; Allonas, X.; Kovalenko, S. A.; Senyushkina, T. A. J. Phys. Chem. A 2010, 114, 13031
11. von der Haar, Th.; Hebecker, A.; Il'ichev, Yu. V.; Jiang, Y.-B.; Kühnle, W.; Zachariasse, K. A. Recl. Trav. Chim. Pays-Bas 1995, 114, 430
12. von der Haar, Th.; Hebecker, A.; Il'ichev, Yu.; Kühnle, W.; Zachariasse, K. A. In Fast Elementary Processes in Chemical and Biological Systems, Lille, France, 1995, AIP Conference Proceedings 1996; Vol. 364, p 295.
13. 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
14. Erratum: J. Photochem. Photobiol. A: Chem. 1998, 115, 259.
15. Zachariasse, K. A. Chem. Phys. Lett. 2000, 320, 8
16. Zachariasse, K. A.; Druzhinin, S. I.; Galievsky, V. A.; Kovalenko, S. A.; Senyushkina, T. A.; Mayer, P.; Noltemeyer, M.; Boggio-Pasqua, M.; Robb, M. A. J. Phys. Chem. A 2009, 113, 2693
17. Gedeck, P.; Schneider, S. J. Photochem. Photobiol. A: Chem. 1999, 121, 7
18. Parusel, A. B. J.; Schamschule, R.; Kohler, G. Z. Phys. Chem. 2002, 216, 361
19. Jamorski, C. J.; Lüthi, H.-P. Chem. Phys. Lett. 2003, 368, 561
20. Gómez, I.; Reguero, M.; Boggio-Pasqua, M.; Robb, M. A. J. Am. Chem. Soc. 2005, 127, 7119
21. Druzhinin, S. I.; Mayer, P.; Stalke, D.; von Bülow, R.; Noltemeyer, M.; Zachariasse, K. A. J. Am. Chem. Soc. 2010, 132, 7730
22. Griffiths, J.; Roozpeikar, B. J. Chem. Soc., Perkin Trans. 1 1976, 42
23. Griffiths, J.; Lockwood, M.; Roozpeikar, B. J. Chem. Soc., Perkin Trans. 2 1977, 1608
24. Adcock, A. D.; Dewar, M. J. S. J. Am. Chem. Soc. 1967, 89, 386
25. Druzhinin, S. I.; Kovalenko, S. A.; Senyushkina, T.; Zachariasse, K. A. J. Phys. Chem. A 2007, 111, 12878
26. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991
27. Galievsky, V. A.; Druzhinin, S. I.; Demeter, A.; Jiang, Y.-B.; Kovalenko, S. A.; Pérez Lustres, L.; Venugopal, K.; Ernsting, N. P.; Allonas, X.; Noltemeyer, M.; Machinek, R.; Zachariasse, K. A. Chem. Phys. Chem. 2005, 6, 2307
28. Kovalenko, S. A.; Dobryakov, A. L.; Ruthmann, J.; Ernsting, N. P. Phys. Rev. A 1999, 59, 2369
29. Ernsting, N. P.; Kovalenko, S. A.; Senyushkina, T. A.; Saam, J.; Farztdinov, V. J. Phys. Chem. A 2001, 105, 3443
30. Heine, A.; Herbst-Irmer, R.; Stalke, D.; Kühnle, W.; Zachariasse, K. A. Acta Crystallogr. 1994, B50, 363
31. Druzhinin, S. I.; Dubbaka, S. R.; Knochel, P.; Kovalenko, S. A.; Mayer, P.; Senyushkina, T.; Zachariasse, K. A. J. Phys. Chem. A 2008, 112, 2749
32. Zachariasse, K. A.; Druzhinin, S. I.; Kovalenko, S. A.; Senyushkina, T. A. J. Chem. Phys. 2009, 131, 224313
33. Zachariasse, K. A.; Druzhinin, S. I.; Kovalenko, S. A.; Senyushkina, T. A. Chem. Phys. Lett. 2009, 484, 28
34. Oshima, J.; Yoshihara, T.; Tobita, S. Chem. Phys. Lett. 2006, 423, 306
35. Dahl, K.; Biswas, R.; Ito, N.; Maroncelli, M. J. Phys. Chem. B 2005, 109, 1563
36. Yoshihara, T.; Druzhinin, S. I.; Demeter, A.; Kocher, N.; Stalke, D.; Zachariasse, K. A. J. Phys. Chem. A 2005, 109, 1497
37. Murrell, J. N. The Theory of Electronic Spectra of Organic Molecules; Methuen: London, 1963.
38. Karpiuk, J.; Karolak, E.; Nowacki, J. Phys. Chem. Chem. Phys. 2010, 12, 8804
39. 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
40. Zachariasse, K. A.; von der Haar, Th.; Leinhos, U.; Kühnle, W. J. Inf. Rec. Mater. 1994, 21, 501
41. 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
42. Zachariasse, K. A.; Druzhinin, S. I.; Bosch, W.; Machinek, R. J. Am. Chem. Soc. 2004, 126, 1705
43. Nelsen, S. F. J. Org. Chem. 1984, 49, 1891
44. Solling, T. I.; Kötting, C.; Zewail, A. H. J. Phys. Chem. A 2003, 107, 10872
45. Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S. Handbook of He(I) Photoelectron Spectra of Fundamental Organic Molecules; Japan Scientific Societies Press: Tokyo, 1981.
46. Il'ichev, Yu. V.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. A 1998, 102, 5670
47. Druzhinin, S. I.; Kovalenko, S. A.; Senyushkina, T. A.; Demeter, A.; Januskevicius, R.; Mayer, P.; Stalke, D.; Machinek, R.; Zachariasse, K. A. J. Phys. Chem. A 2009, 113, 9304
48. Baumann, W.; Bischof, H.; Brittinger, J.-C.; Rettig, W.; Rotkiewicz, K. J. Photochem. Photobiol. A: Chem. 1992, 64, 49
49. Yoshihara, T.; Galievsky, V. A.; Druzhinin, S. I.; Saha, S.; Zachariasse, K. A. Photochem. Photobiol. Sci. 2003, 2, 342
50. Il'ichev, Yu. V.; Kühnle, W.; Zachariasse, K. A. Chem. Phys. 1996, 211, 441
51. Suppan, P.; Ghoneim, N. Solvatochromism; The Royal Society of Chemistry: Cambridge, U.K., 1997.
52. Liptay, W. In Excited States; Lim, E. C., Ed.; Academic Press: New York, USA, 1974; Vol. 1, p 129.
53. Galievsky, V. A.; Druzhinin, S. I.; Demeter, A.; Mayer, P.; Kovalenko, S. A.; Senyushkina, T. A.; Zachariasse, K. A. J. Phys. Chem. A 2010, 114, 12622
54. Demeter, A.; Druzhinin, S.; George, M.; Haselbach, E.; Roulin, J.-L.; Zachariasse, K. A. Chem. Phys. Lett. 2000, 323, 351
55. Schuddeboom, W.; Jonker, S. A.; Warman, J. M.; Leinhos, U.; Kühnle, W.; Zachariasse, K. A. J. Phys. Chem. 1992, 96, 10809
56. Herbich, J.; Rotkiewicz, K.; Waluk, J.; Andresen, B.; Thulstrup, E. W. Chem. Phys. 1989, 138, 105
57. Zachariasse, K. A.; Yoshihara, T.; Druzhinin, S. I. J. Phys. Chem. A 2002, 106, 6325
58. Yoshihara, T.; Druzhinin, S. I.; Zachariasse, K. A. J. Am. Chem. Soc. 2004, 126, 8535
59. Zachariasse, K. A.; Druzhinin, S. I.; Kovalenko, S. A.; Senyushkina, T. A. J. Phys. Chem. A 2010, 114, 1621
60. Druzhinin, S. I.; Galievsky, V. A.; Yoshihara, T.; Zachariasse, K. A. J. Phys. Chem. A 2006, 110, 12760
61. Maçanita, A. L.; Zachariasse, K. A. J. Phys. Chem. A 2011, 115, 3183
62. Landolt-Börnstein, Numerical Data and Functional Relationships in Science and Technology, New Series; Madelung, O., Ed.; Group IV; Springer: Berlin, 1991; Vol. 6.
63. Birks, J. B. Photophysics of Aromatic Molecules; Wiley: London, 1970.
64. Hirayama, S.; Phillips, D. J. Photochem. 1980, 12, 139
65. Morris, J. V.; Mahaney, M. A.; Huber, J. R. J. Phys. Chem. 1976, 80, 969
66. Saltiel, J.; Waller, A. S.; Sears, D. F.; Garrett, C. Z. J. Phys. Chem. 1993, 97, 2516
67. Toptygin, D. J. Fluoresc. 2003, 13, 201