Environmental photochemistry of nitro-PAHs: Direct observation of ultrafast intersystem crossing in 1-nitropyrene

Journal of Physical Chemistry A

Volumn 112, Issue 28, 2008, Pages 6313-6319

  Crespo Hernández, Carlos E ^a   Burdzinski, Gotard ^b   Arce, Rafael ^c  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

^c UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

DIRECT OBSERVATION; FEMTO SECONDS; FRANCK-CONDON; HEXANE SOLUTIONS; INTERSYSTEM CROSSING; TRANSIENT ABSORPTION; TRANSIENT ABSORPTION SPECTRA; ULTRA-FAST;

AROMATIC COMPOUNDS; AROMATIC HYDROCARBONS; HEXANE; HYDROCARBONS; ORGANIC COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS;

ABSORPTION;

1 NITROPYRENE; 1-NITROPYRENE; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE DERIVATIVE; SOLVENT;

ARTICLE; CHEMISTRY; CONFORMATION; PHOTOCHEMISTRY; POLLUTANT; SPECTROSCOPY;

ENVIRONMENTAL POLLUTANTS; MOLECULAR CONFORMATION; PHOTOCHEMISTRY; POLYCYCLIC HYDROCARBONS, AROMATIC; PYRENES; SOLVENTS; SPECTRUM ANALYSIS;

EID: 50249124796     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp803847q     Document Type: Article

References (56)

1. Yu, H. J. Environ. Sci. Health C 2002, C20, 149.
2. Arlt, V. M. Mutagenesis 2005, 20, 399.
3. Tokiwa, H.; Ohnishi, Y. CRC Crit. Rev. Toxicol. 1986, 17, 23.
4. Möller, L. Environ. Health Perspect. 1994, 102, 139.
5. Purohit, V.; Basu, A. K. Chem. Res. Toxicol. 2000, 13, 673.
6. Christensen, H. C. J. Phys. Chem. 1973, 77, 983.
7. Diesel and Gasoline Engine Exhausts and Some Nitroarenes. In IARC Monographs on the Evaluation of Carcinogenic Risks to Humans; World Health Organization, International Agency for Research on Cancer; Lyon, France, 1989; No. 46.
8. Finlayson-Pitts, B. J.; Pitts, J. N. Science 1997, 276, 1045.
9. Atkinson, R.; Arey, J. Environ. Health Perspect. 1994, 102, 117.
10. Arey, J. Atmospheric Reactions of PAHs Including Formation of Nitroarenes. In PAHs and Related Compounds; Neison, A. H., Ed.; Springer-Verlag: Berlin, Germany, 1998; p 347.
11. Arey, J.; Atkinson, R. Photochemical Reactions of PAHs in the Atmosphere. In PAHs: An Ecotoxicological Perspective; Douben, P. E. T., Ed.; John Wiley & Sons: Chichester, England, 2003; p 47.
12. Chapman, O. L.; Heckert, D. C.; Reasoner, J. W.; Thackaberry. S. P. J. Am. Chem. Soc. 1966, 88, 5550.
13. Warner, S. D.; Farant, J.-P.; Butler, I. S. Chemosphere 2004, 54, 1207.
14. Arey, J.; Zielinska, B.; Atkinson, R.; Winer, A. M. Mutat. Res. 1988, 207, 45.
15. Hayakawa, K.; Murahashi, T.; Butoh, M.; Miyazaki, M. Environ. Sci. Technol. 1995, 29, 928.
16. Hayakawa, K.; Nakamura, A.; Terai, N.; Kizu, R.; Ando. K. Chem. Pharm. Bull. 1997, 45, 1820.
17. Salmeen, I.; Durisin, A. M.; Prater, T. J.; Riley, T. Mutat. Res. 1982, 104, 17.
18. Kawanaka, Y.; Sakamoto, K.; Wang, N.; Yun, S.-J. J. Chromatogr. A 2007, 1163, 312.
19. Holloway, M. P.; Biaglow, M. C.; McCoy, E. C.; Anders, M.; Rosenkranz, H. S.; Howard, P. C Mutat. Res. 1987, 187, 199.
20. Yang, D. T. C.; Chou, A.; Chen, E.; Chiu, L.H.; Ni, Y. Polycycl. Arom. Compd. 1994, 5, 201.
21. Yasahara, A.; Huwa, K. Chem. Lett. (Jpn.) 1983, 347.
22. Koizumi, A.; Suzuki, T.; Saitoh, N.; Kamiyama, S. A. Arch. Environ. Health 1994, 49, 87.
23. Pitts, J. N.; van Cauwenberghe, K. A.; Grosjean, D.; Schmid, J. P.; Fitz, D. R.; Belser, W. L.; Knudson, G. B.; Hynds, P. M. Science 1978, 202, 515.
24. Stark, G.; Stauff, J.; Miltenburger, H. G.; Stumm-Fischer, I. Mutat. Res. 1985, 155, 27.
25. Ioki, Y. J. Chem. Soc., Perkin Trans. 2 1977, 1240.
26. Fukuhara, K.; Kurihara, M.; Miyata, N. J. Am. Chem. Soc. 2001, 123, 8662.
27. Burdzinski, G.; Hackett, J. C.; Wang, J.; Gustafson, T. L.; Hadad, C. M.; Platz, M. S. J. Am. Chem. Soc. 2006, 128, 13402.
28. Nakayama, T.; Amijima, Y.; Ibuki, K.; Hamanoue, K. Rev. Sci. Instrum. 1997, 68, 4364.
29. Burdzinski, G.; Maciejewski, A.; Buntinx, G.; Poizat, O.; Lefumeux, C. Chem. Phys. Lett. 2004, 384, 332.
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, K. N.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, revision D.01; Gaussian, Inc.: Wallingford, CT, 2004.
31. Becke, A. D. J. Chem. Phys. 1993, 98, 1372.
32. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785.
33. Momany, E. A.; Willett, J. L. J. Comput. Chem. 2000, 21, 1204.
34. Cramer, C. J. Essentials of computational chemistry: theories and models; John Wiley & Sons: New York, 2002.
35. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210.
36. Cances, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032.
37. Onchoke, K. K.; Hadad, C. M.; Dutta, P. K. Polycycl. Arom. Compd. 2004, 24, 37.
38. Jung, H.; Shaikh, A. U.; Heflich, R. H.; Fu, P. P. Environ. Mol. Mutagen. 1991, 17, 169.
39. Miller, D. W.; Evans, F. E.; Fu, P. P. Spectrosc Int. J. 1985, 4, 91.
40. Lin, S.-T.; Jih, Y.-F.; Fu, P. P. J. Org. Chem. 1996, 61, 5271.
41. Improta, R.; Barone, V.; Santero, F. J. Phys. Chem. B 2007, 111, 14080.
42. Note that the transient absorption spectra might be affected by stimulated emission (negative signal), particularly around 450 nm where the weak stationary emission of INP peaks (see steady state emission spectrum of INP in the Supporting Information).
43. Arce, R.; Pino, E. F.; Valle, C.; Ágreda, J. J. Phys. Chem. A, submitted for publication.
44. Morales-Cueto, R.; Esquivelzeta-Rabell, M.; Saucedo-Zugazagoitia, J.; Peon, J. J. Phys. Chem. A 2007, 111, 552.
45. Kasha, M. Radiat. Res. Suppl. 1960, 2, 243.
46. Scheerer, R.; Henglein, A. Ber. Bunsen-Ges. 1977, 81, 1234.
47. Lim, E. C. J. Phys. Chem. 1986, 90, 6770.
48. El-Sayed, M. A. J. Chem. Phys. 1962, 36, 573.
49. El-Sayed, M. A. J. Chem. Phys. 1963, 38, 2834.
50. Fu, P. P.; Chou, M. W.; Beland, F. A. Effects of nitro substitution on the in vitro metabolic activation of polycyclic aromatic hydrocarbons; CRC Press: Boca Raton, FL, 1988; Vol. II.
51. Fu, P. P.; Herrero-Saenz, D. Environ. Carcinog. Ecotox. Rev. 1999, C17, 1.
52. Fu, P. P. Drug Metabolism Rev. 1990, 22, 209.
53. He, Y.; Gahlmann, A.; Feenstra, J. S.; Park, S. T.; Zewail, A. H. Chem. Asian. J. 2006, 1-2, 56.
54. Hamanoue, K.; Nakayama, T.; Ushida, K.; Kajiwara, K.; Yamanaka, S. J. Chem. Soc., Faraday Trans. 1991, 87, 3365.
55. Hamanoue, K.; Nakayama, T.; Kajiwara, K.; Yamanaka, S. J. Chem. Soc., Faraday Trans. 1992, 88, 3145.
56. Brown, H. W.; Pimentel, G. C. J. Chem. Phys. 1958, 29, 883.