Effect of strain on the photoisomerization and stability of a congested azobenzenophane: A combined experimental and computational study

Journal of Physical Chemistry A

Volumn 110, Issue 45, 2006, Pages 12385-12394

  Bassotti, Elisa ^a   Carbone, Paola ^a   Credi, Alberto ^a   Di Stefano, Marco ^a   Masiero, Stefano ^a,b   Negri, Fabrizia ^a,b   Orlandi, Giorgio ^a,b   Spada, Gian Piero ^a,b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b INSTM   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; COMPUTATIONAL METHODS; PARAFFINS; PHOTOCHEMICAL REACTIONS; REACTION KINETICS;

EXCITATION ENERGIES; PHOTOCHEMICAL REACTIVITY; PHOTOISOMERIZATION;

ISOMERIZATION;

EID: 33751246456     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp062428b     Document Type: Article

References (35)

1. Rau, H. In Photochromism: Molecules and Systems; Dürr, H., Bouas-Laurent, H., Eds.; Elsevier: Amsterdam, 2003; pp 165-92.
2. Murakami, H.; Kawabuchi, A.; Matsumoto, R.; Ido, T.; Nakashima, N. J. Am. Chem. Soc. 2005, 127, 15891-9.
3. Hugel, T.; Holland, N. B.; Cattani, A.; Moroder, L.; Seitz, M.; Gaub, H. E. Science 2002, 296, 1103-6.
4. Norikane, Y.; Tamaoki, N. Org. Lett. 2004, 6, 2595-8.
5. Nagamani, S. A.; Norikane, Y.; Tamaoki, N. J. Org. Chem. 2005, 70, 9304-13.
6. Jousselme, B.; Blanchard, P.; Gallego-Planas, N.; Delaunay, J.; Allain, M.; Richomme, P.; Levillain, E.; Roncali, J. J. Am. Chem. Soc. 2003, 125, 2888-9.
7. Qu, D. H.; Wang, Q. C.; Ma, X.; Tian, H. Chem. - Eur. J. 2005, 11, 5929-37.
8. Rau, H.; Lueddecke, E. J. Am. Chem. Soc. 1982, 104, 1616-20.
9. Tamaoki, N.; Ogata, K.; Koseki, K.; Yamaoka, T. Tetrahedron 1990, 46, 5931-42.
10. Tamaoki, N.; Koseki, K.; Yamaoka, T. Angew. Chem., Int. Ed. Engl. 1990, 29, 105-6.
11. Tauer, E.; Machinek, R. Liebigs Ann. 1996, 1213-6.
12. Norikane, Y.; Kitamoto, K.; Tamaoki, N. Org. Lett. 2002, 4, 3907-10.
13. Norikane, Y.; Kitamoto, K.; Tamaoki, N. J. Org. Chem. 2003, 68, 8291-304.
14. Pieraccini, S.; Gottarelli, G.; Labruto, R.; Masiero, S.; Pandoli, O.; Spada, G. P. Chem. - Eur. J. 2004, 10, 5632-9.
15. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London 1956, 253, 518.
16. Fischer, E. EPA Newsletter 1984, 20, 33.
17. Montalti, M.; Credi, A.; Prodi, L.; Gandolfi, M. T. Handbook of Photochemistry, 3rd ed.; CRC Press: Boca Raton, 2006.
18. Allinger, N. L.; Yuh, H. Y.; Lii, J. H. J. Am. Chem. Soc. 1989, 111, 8551-66.
19. Ponder, J. W. TINKER, Software Tools for Molecular Design, version 3.8 (1990-2003); http://dasher.wustl.edu/tinker.
20. Bacon, A. D.; Zerner, M. C. Theor. Chim. Acta 1979, 53, 21.
21. Gaussian 03, Revision B.1; Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc.: Pittsburgh, PA, 2003.
22. Molekel, Version 4.3, http://www.cscs.ch/molekel/.
23. Portmann, S.; Lüthi, H. P. Chimia 2000, 54, 766.
24. Hirose, Y.; Yui, H.; Sawada, T. J. Phys. Chem. A 2002, 106, 3067-71.
25. Halpern, J.; Brady, G. W.; Winkler, C. A. Can. J. Res., Sect. B 1950, 28, 140.
26. Gabor, G.; Fischer, E. J. Phys. Chem. 1971, 75, 581-3.
27. 1H NMR spectrum recorded at 25 and -20°C revealed only the presence of the signals of the tt form: the signals of any other species possibly present, if any, are not distinguishable from the background noise in these experimental conditions.
28. Adamson, A. W.; Vogler, A.; Kunkely, H.; Wachter, R. J. Am. Chem. Soc. 1978, 100, 1298-300.
29. Corruccini, R. J.; Gilbert, E. C. J. Am. Chem. Soc. 1939, 61, 2925-7.
30. Cembran, A.; Bernardi, F.; Garavelli, M.; Gagliardi, L.; Orlandi, G. J. Am. Chem. Soc. 2004, 126, 3234-43.
31. Gagliardi, L.; Orlandi, G.; Bernardi, F.; Cembran, A.; Garavelli, M. Theor. Chem. Acc. 2004, 111, 363-72.
32. Cisnetti, F.; Ballardini, R.; Credi, A.; Gandolfi, M. T.; Masiero, S.; Negri, F.; Pieraccini, S.; Spada, G. P. Chem. - Eur. J. 2004, 10, 2011-21.
33. Molecular Switches; Feringa, B. L., Ed.; Wiley-WCH: Weinheim, 2001.
34. Credi, A. Aust. J. Chem. 2006, 59, 157-69.
35. Muraoka, T.; Kinbara, K.; Aida, T. Nature 2006, 440, 512-5.