Excited-state intramolecular proton transfer in hydroxyoxime-based chemical sensors

Journal of Physical Chemistry A

Volumn 115, Issue 5, 2011, Pages 834-840

  Kerkines, Ioannis S K ^a   Petsalakis, Ioannis D ^a   Theodorakopoulos, Giannoula ^a   Rebek Jr , Julius ^b  

^a THEORETICAL AND PHYSICAL CHEMISTRY INSTITUTE   (Greece)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC CORES; BASIS SETS; COUPLED CLUSTERS; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; FLUORESCENCE QUENCHING; FLUORESCENT SENSORS; HYDROXYL GROUPS; HYDROXYOXIMES; INTRAMOLECULAR PROTON TRANSFER; NERVE AGENTS; NITROGEN ATOM; SECOND ORDERS; TIME DEPENDENT DENSITY FUNCTIONAL THEORY;

DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; EXCITED STATES; FLUORESCENCE; PROTON TRANSFER; SENSORS;

NAPHTHALENE;

COUMARIN; COUMARIN DERIVATIVE; ISOXAZOLE DERIVATIVE; NAPHTHALENE; NAPHTHALENE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; OXIME; PROTON; PYRENE; PYRENE DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; QUANTUM THEORY; SPECTROFLUOROMETRY;

COUMARINS; FLUORESCENCE; ISOXAZOLES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NAPHTHALENES; ORGANOPHOSPHORUS COMPOUNDS; OXIMES; PROTONS; PYRENES; PYRIDINES; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE;

EID: 79851492483     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp1088433     Document Type: Article

References (38)

1. (a) Tuovinen, K. Toxicology 2004, 196, 31.
2. (b) Sidell, F. R.; Borak, J. Ann. Emerg. Med. 1992, 21, 865.
3. See for instance: Burnworth, M.; Rowan, S. J.; Weder, C. Chem. Eur. J. 2007, 13, 7828.
4. van Houten, K. A.; Heath, D. C.; Pilato, R. S. J. Am. Chem. Soc. 1998, 120, 12359.
5. Zhang, S.-W.; Swager, T. J. Am. Chem. Soc. 2003, 125, 3420.
6. Dale, T. J.; Rebek, J., Jr. J. Am. Chem. Soc. 2006, 128, 4500.
7. Costero, A. M.; Gil, S.; Parra, M.; Mancini, P. M. E.; Martínez-Máñez, R.; Sancenón, F.; Royo, S. Chem. Commun. 2008, 6002.
8. Feuster, E. K.; Glass, T. E. J. Am. Chem. Soc. 2003, 125, 16174.
9. Wu, Y.; Peng, X.; Fan, J.; Gao, S.; Tian, M.; Zhao, J.; Sun, S. J. Org. Chem. 2007, 72, 62.
10. Ma, Q.-J.; Zhang, X.-B.; Zhao, X.-H.; Gong, Y.-J.; Tang, J.; Shen, G.-L.; Yu, R.-Q. Spectrochim. Acta, Part A 2009, 73, 687.
11. Petsalakis, I. D.; Lathiotakis, N. N.; Theodorakopoulos, G. J. Mol. Struct. (THEOCHEM) 2008, 867, 64.
12. Petsalakis, I. D.; Kerkines, I. S. K.; Lathiotakis, N. N.; Theodorakopoulos, G. Chem. Phys. Lett. 2009, 474, 278.
13. Wallace, K. J.; Fagbemi, R. I.; Folmer-Anderson, F. J.; Morey, J.; Lynth, V. M.; Anslyn, E. V. Chem. Commun. 2006, 3886.
14. Dale, T. J.; Rebek, J., Jr. Angew. Chem., Int. Ed. 2009, 48, 7850.
15. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
16. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
17. Yanai, T.; Tew, D.; Handy, N. Chem. Phys. Lett. 2004, 393, 51.
18. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999 and references therein..
19. (a) Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257.
20. (b) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
21. (c) McLean, A. D.; Chandler, G. S. J. Chem. Phys. 1980, 72, 5639.
22. (d) Ragavachari, K.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
23. (a) Christiansen, O.; Koch, H.; Jørgensen, P. Chem. Phys. Lett. 1995, 243, 409.
24. (b) Hättig, C.; Köhn, A. J. Chem. Phys. 2002, 117, 6939.
25. (c) Hättig, C.; Weigend, F. J. Chem. Phys. 2000, 113, 5154.
26. (d) Hättig, C. J. Chem. Phys. 2003, 118, 7751.
27. (e) Köhn, A.; Hättig, C. J. Chem. Phys. 2003, 119, 5021.
28. (a) Schäfer, A.; Horn, C.; Ahlrichs, R. J. Chem. Phys. 1992, 97, 2571.
29. (b) Schäfer, A.; Huber, C.; Ahlrichs, R. J. Chem. Phys. 1994, 100, 5829.
30. (a) Weigend, F.; Häser, M.; Patzelt, H.; Ahlrichs, R. Chem. Phys. Lett. 1998, 294, 143.
31. (b) Weigend, F.; Köhn, A.; Hättig, C. J. Chem. Phys. 2001, 116, 3175.
32. Stein, T.; Kronik, L.; Baer, R. J. Chem. Phys. 2009, 131, 244119.
33. Stein, T.; Kronik, L.; Baer, R. J. Am. Chem. Soc. 2009, 131, 2818.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B. et al. Gaussian 09, Revision D.01; Gaussian Inc., Wallingford, CT, 2004.
35. TURBOMOLE V6.1 2009, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007; available from http://www.turbomole.com.
36. Lefebvre-Brion, H.; Field, R. W. In The Spectra and Dynamics of Diatomic Molecules; Elsevier Academic Press: Amsterdam, 2004.
37. Kerkines, I. S. K.; Petsalakis, I. D.; Theodorakopoulos, G.; Klopper, W. J. Chem. Phys. 2009, 131, 224315.
38. Chai, J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615.