Acidoswitchable NLO-phores; Benzimidazolo[2,3-b]oxazolidines

Journal of Physical Chemistry B

Volumn 110, Issue 22, 2006, Pages 10672-10682

  Sanguinet, Lionel ^a   Pozzo, Jean Luc ^a   Guillaume, Maxime ^b   Champagne, Benoît ^b   Castet, Frédéric ^c   Ducasse, Laurent ^c   Maury, Etienne ^c   Soulié, Jérémy ^c   Mançois, Fabien ^c   Adamietz, Frédéric ^c   Rodriguez, Vincent ^c  

^a Chimie Supramoléculaire Biomimétisme et Nanoscience UMR 5802 CNRS   (France)

^b UNIVERSITY OF NAMUR   (Belgium)

^c UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; ORGANIC COMPOUNDS; ORGANIC SOLVENTS; REACTION KINETICS; TEMPERATURE;

ACIDOCHROMIC BEHAVIOR; NLO RESPONSE; PHENYLETHENYL; THEORETICAL CALCULATIONS;

NITROGEN COMPOUNDS;

EID: 33745461164     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp060825g     Document Type: Article

References (57)

1. (a) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
2. (b) Lucas, L.; De Jong, J.; Van Esch, J.; Kellogg, R. M.; Feringa, B. L. Eur. J. Org. Chem. 2003, 1, 155.
3. Delaire, J. A.; Nakatani, K. Chem. Rev. 2000, 100, 1817.
4. (a) Atassi, Y.; Delaire, J. A.; Nakatani, K. J. Phys. Chem. Rev. 1995, 99, 16320.
5. (b) Barachevsky, V.; Chudinova, G. Mol. Sci. Eng. C 1999, 8-9, 73.
6. (a) Pina, F.; Melo, M. J.; Maestri, M.; Ballardini, R.; Balzani, V. J. Am. Chem. Soc. 1997, 119, 5556.
7. (b) Organic Photochromic and Thermochromic Compounds, Crano, J. C., Guglielmetti, R. J., Eds.; Plenum Press: New York, 1999; Vol. 1.
8. (c) Bouas-Laurent, H.; Dürr, H. Pure Appl. Chem. 2001, 73, 639.
9. Sanguinet, L.; Pozzo, J. L.; Rodriguez, V.; Adamietz, F.; Castet, F.; Ducasse, L.; Champagne, B. J. Phys. Chem. B 2005, 109, 11139.
10. (a) Wortmann, R.; Krämer, P.; Glania, C.; Lebus, S.; Detzer, N. Chem. Phys. Lett. 1993, 173, 99.
11. (b) Meyers, F.; Marder, S.; Pierce, B. M.; Brédas, J. L. J. Am. Chem. Soc. 1994, 116, 10703.
12. (c) Verbiest, T.; Houbrechts, S.; Kauranen, M.; Clays, K.; Persoons, A. J. Mater. Chem. 1997, 7, 2175.
13. (d) Raimundo, J. M.; Blanchard, P.; Gallego-Planas, N.; Mercier, N.; Ledoux-Rak, I.; Hierle, R.; Roncali, J. J. Org. Chem. 2002, 67, 205.
14. (e) Cho, M.; Am, S. Y.; Lee, H.; Ledoux, I.; Zyss, J. J. Chem. Phys. 2002, 116, 9165.
15. (f) Brunel, J.; Mongin, O.; Jutand, A.; Ledoux, I.; Zyss, J.; Blanchard-Desce, M. Chem. Mater. 2003, 15, 4139.
16. (g) Champagne, B.; André, J. M.; Botek, E.; Licandro, E.; Maiorana, S.; Bossi, A.; Clays, K.; Persoons, A. ChemPhysChem 2004, 5, 1438.
17. (h) Frediani, L.; Ågren, H.; Ferrighi, L.; Ruud, K. J. Chem. Phys. 2005, 123, 144117.
18. (i) Chen, W.; Li, Z. R.; Wu, D.; Li, Li, Y.; Sun, C. C.; Gu, F. L. J. Am. Chem. Soc. 2005, 127, 10977.
19. (j) Maury, O.; Le Bozec, H. Acc. Chem. Res. 2005, 38, 691.
20. (a) Clays, K.; Persoons, A.; De Maeyer, L. Adv. Chem. Phys. 1994, 85, 455.
21. (b) Hendrickx, E.; Clays, K.; Persoons, A. Acc. Chem. Res. 1998, 31, 675.
22. (a) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195.
23. (b) Champagne, B.; Kirtman, B. In Handbook of Advanced Electronic and Photonic Materials and Devices; Nalwa, H. S., Ed.; Academic Press: New York, 2001, Vol. 9, Chapter 2, p 63.
24. Bersohn, R.; Pao, Y. H.; Frisch, H. L. J. Chem. Phys. 1966, 45, 3184.
25. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; 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 03, Revision C.02, Gaussian, Inc., Pittsburgh, PA, 2003.
26. (a) Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111.
27. (b) Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1976, 42, 223.
28. (c) Bacon, A. D.; Zerner, M. C. Theor. Chim. Acta 1979, 53, 21.
29. (d) Zerner, M. C.; Loew, G. H.; Kirchner, R. F.; Mueller-Westerhoff, U. T. J. Am. Chem. Soc. 1980, 102, 589.
30. MOS-F (Semiempirical Molecular Orbital package for Spectroscopy), Fujitsu V4.
31. (a) Zerner, M. C. In Reviews of Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1991; Vol. 1, p 313.
32. (b) Martin, C. H.; Zerner, M. C. In Inorganic Electronic Structure and Spectroscopy, Solomon, E. I., Lever, A. B. P., Eds.; Wiley: New York, 1999; Vol. 1, p 555.
33. See for example, in the case of second-order NLO responses:
34. (a) Meyers, F.; Brédas, J. L.; Zyss, J. J. Am. Chem. Soc. 1992, 114, 2914.
35. (b) Dehu, C.; Meyers, F.; Hendrickx, E.; Clays, K.; Persoons, A.; Marder, S. R.; Brédas, J. L. J. Am. Chem. Soc. 1995, 117, 10127.
36. See for example, (a) Morley, J. O. J. Chem. Soc., Faraday Trans. 1991, 87, 3009.
37. (b) Morley, J. O. J. Phys. Chem. 1995, 99, 10166.
38. See for example (a) Kanis, D. R.; Ratner, M. A.; Marks, T. J.; Zerner, M. C. Chem. Mater. 1991, 3, 19.
39. (b) Albert, I. D. L.; Marks, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 9714.
40. (a) Sekino, H.; Bartlett, R. J. J. Chem. Phys. 1986, 85, 976.
41. (b) Karna, S. P.; Dupuis, M. J. Comput. Chem. 1991, 12, 487.
42. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
43. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
44. Stewart, J. J. P. J. Mol. Mod. 2004, 10, 6.
45. (a) Castet, F.; Champagne, B. J. Phys. Chem. A 2001, 105, 1366.
46. (b) Botek, E.; Champagne, B. J. Appl. Phys. B 2002, 74, 627.
47. (c) Guillaume, M.; Botek, E.; Champagne, B.; Castet, F.; Ducasse, L. J. Chem. Phys. 2005, 121, 7390.
48. MOPAC2000, Fujitsu Limited, 1999; Stewart, J. J. P. Quantum Chemistry Program Exchange, no. 455.
49. Cohen, H. D.; Roothaan, C. C. J. J. Chem. Phys. 1965, 43, S34.
50. Davis, P. J.; Rabinowitz, P. In Numerical Integration; Blaisdell Publishing Company: London, 1967, p 166.
51. (a) Rice, M. J.; Handy, N. Int. J. Quantum Chem. 1992, 43, 91.
52. (b) Sekino, H.; Bartlett, R. J. Chem. Phys. Lett. 1995, 234, 87.
53. (c) Jacquemin, D.; Champagne, B.; Hättig, C. Chem. Phys. Lett. 2000, 319, 327.
54. Bulat, F. A.; Toro-Labbé, A.; Champagne, B.; Kirtman, B.; Yang, W. J. Chem. Phys. 2005, 123, 014319.
55. Willetts, A.; Rice, J. E.; Burland, D. A.; Shelton, D. P. J. Chem. Phys. 1992, 97, 7590.
56. Bersohn, R.; Pao, Y. H.; Frisch, H. L. J. Chem. Phys. 1966, 45, 3184.
57. Würthner, F.; Yao, S.; Debaerdemaeker, T.; Wortmann, R. J. Am. Chem. Soc. 2002, 124, 9431.