Charge resonance excitations in 1,3-Bis[di(4-methoxyphenyl)amino]azulene radical cations

Journal of Physical Chemistry C

Volumn 111, Issue 8, 2007, Pages 3512-3516

  Nöll, Gilbert ^a,b   Amthor, Stephan ^c   Avola, Manuele ^a   Lambert, Christoph ^c   Daub, Jörg ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b LUND UNIVERSITY   (Sweden)

^c UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AZULENE; CHARGE RESONANCE EXCITATIONS; ELECTROCHEMICAL STABILITY; ELECTRONIC COUPLING; RADICAL CATIONS;

DERIVATIVES; FREE RADICALS; OXIDATION; POSITIVE IONS; REDOX REACTIONS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

EID: 33947419744     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp066385a     Document Type: Article

References (38)

1. Lambert, C.; Risko, C.; Coropceanu, V.; Schelter, J.; Amthor, S.; Gruhn, N. E.; Durivage, J. C.; Bredas, J.-L. J. Am. Chem. Soc. 2005, 127, 8508.
2. Schneider, J. J.; Spickermann, D.; Labahn, T.; Magull, J.; Fontani, M.; Laschi, F.; Zanello, P. Chem.-Eur. J. 2000, 6, 3686.
3. Barybin, M. V.; Chisholm, M. H.; Dalal, N. S.; Holovics, T. H.; Patmore, N. J.; Robinson, R. E.; Zipse, D. J. J. Am. Chem. Soc. 2005, 127, 15182.
4. Lambert, C.; Nöll, G.; Kriegisch, V.; Zabel, M.; Hampel, F.; Schmälzlin, E.; Meerholz, K.; Bräuchle, C. Chem.-Eur. J. 2003, 9, 4232.
5. Lambert, C.; Amthor, S.; Schelter, J. J. Phys. Chem. A 2004, 108, 6474.
6. Lambert, C.; Nöll, G. J. Am. Chem. Soc. 1999, 121, 8434.
7. Bonvoisin, J.; Launay, J.-P.; Verbouwe, W.; Van der Auweraer, M.; De Schryver, F. C. J. Phys. Chem. 1996, 100, 17079.
8. Nelsen, S. F. Electron Transfer Reactions in Organic Chemistry. In Electron Transfer in Chemistry I. Principles and Theories Methods and Techniques; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. I; pp 342.
9. Noell, G.; Avola, M. J. Phys. Org. Chem. 2006, 19, 238.
10. Newton, M. D. Electron Transfer: Theoretical Models and Computational Implementation. In Electron Transfer in Chemistry I. Principles and Theories Methods and Techniques; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1; pp 3.
11. Newton, M. D. Adv. Chem. Phys. 1999, 106, 303.
12. Bailey, S. E.; Zink, J. I.; Nelsen, S. F. J. Am. Chem. Soc. 2003, 125, 5939.
13. Nelsen, S. F.; Newton, M. D. J. Phys. Chem. A 2000, 104, 10023.
14. Sun, D.; Rosokha, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2004, 126, 1388.
15. Sun, D.; Rosokha, S. V.; Kochi, J. K. Angew. Chem., Int. Ed. 2005, 44, 5133.
16. Zheng, S.; Barlow, S.; Risko, C.; Kinnibrugh, T. L.; Khrustalev, V. N.; Jones, S. C.; Antipin, M. Y.; Tucker, N. M.; Timofeeva, T. V.; Coropceanu, V.; Bredas, J.-L.; Marder, S. R. J. Am. Chem. Soc. 2006, 128, 1812.
17. Barlow, S.; Risko, C.; Chung, S.-J.; Tucker, N. M.; Coropceanu, V.; Jones, S. C.; Levi, Z.; Bredas, J.-L.; Marder, S. R. J. Am. Chem. Soc. 2005, 127, 16900.
18. Amthor, S.; Lambert, C. J. Phys. Chem. A 2006, 110, 1177.
19. Lambert, C.; Nöll, G. Synth. Met. 2003, 139, 57.
20. Hafner, K.; Patzelt, H.; Kaiser, H. Liebigs Annal. Chem. 1962, 656, 24.
21. Salbeck, J. Anal. Chem. 1993, 65, 2169.
22. Ahlrichs, R.; Bär, M.; Baron, H.-P.; Bauernschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Haase, F.; Häser, M.; Hättig, C.; Horn, H.; Huber, C.; Huniar, U.; Kattannek, M.; Köhn, A.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A.; Schneider, U.; Treutler, O.; Tsereteli, K.; Unterreiner, B.; von Arnim, M.; Weigend, F.; Weis, P.; Weiss, H. TURBOMOLE V5.6; Quantum Chemistry Group, University of Karlsruhe: Karlsruhe, Germany, 2002.
23. Flükiger, P.; Lüthi, H. P.; Portmann, S.; Weber, J. F. W. MOLEKEL 4.3; Swiss Center for Scientific Computing: Manno, Switzerland; 2000-2002.
24. Mitchell, R. H.; Chen, Y.; Zhang, J. Org. Prep. Proc. Int. 1997, 29, 715.
25. Redl, F. X.; Köthe, O.; Röckl, K.; Bauer, W.; Daub, J. Macromol. Chem. Phys. 2000, 201.
26. Michl, J.; Thulstrup, E. W. Tetrahedron 1976, 32, 205.
27. Szeghalmi, A. V.; Erdmann, M.; Engel, V.; Schmitt, M.; Amthor, S.; Kriegisch, V.; Nöll, G.; Stahl, R.; Lambert, C.; Leusser, D.; Stalke, D.; Zabel, M.; Popp, J. J. Am. Chem. Soc. 2004, 126, 7834.
28. Coropceanu, V.; Gruhn, N. E.; Barlow, S.; Lambert, C.; Durivage, J. C.; Bill, T. G.; Nöll, G.; Marder, S. R.; Bredas, J.-L. J. Am. Chem. Soc. 2004, 126, 2727.
29. Linstrom, P. J., Mallard, W. G., Eds. NIST Chemistry WebBook; NIST Standard Reference Database Number 69; National Institute of Standards and Technology: Gaithersburg MD (http://webbook.ntst.gov), June 2005.
30. Amthor, S.; Noller, B.; Lambert, C. Chem. Phys. 2005, 316, 141.
31. Schelter, J. Dissertation, University of Würzburg, 2003. Available online: http://opus.bibliothek.uni-wuerzburg.de/opus/volltexte/2004/837.
32. Nelsen, S. F.; Weaver, M. N.; Zink, J. I.; Telo, J. P. J. Am. Chem. Soc. 2005, 127, 10611.
33. Pommerehne, J.; Vestweber, H.: Guss, W.; Mahrt, R. F.; Bässler, H.; Porsch, M.; Daub, J. Adv. Mater. 1995, 7, 551.
34. Nöll, G.; Avola, M.; Lynch, M.; Daub, J. J. Phys. Chem. C, accepted for publication.
35. Thanh, N. C.; Ikai, M.; Kajioka, T.; Fujikawa, H.; Taga, Y.; Zhang, Y.; Ogawa, S.; Shimada, H.; Miyahara, Y.; Kuroda, S.; Oda, M. Tetrahedron 2006, 62, 11227.
36. Ohta, A.; Thanh, N. C.; Terasawa, K.; Fujimori, K.; Kuroda, S.; Oda, M. Tetrahedron Lett. 2006, 47, 2815.
37. Salman, H.; Abraham, Y.; Tal, S.; Meltzman, S.; Kapon, M.; Tessler, N.; Speiser, S.; Eichen, Y. Eur. J. Org. Chem. 2005, 2207.
38. Forsch, M.; Sigl-Seifert, G.; Daub, J. Adv. Mater. 1997, 9, 635.