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International Journal of Photoenergy
Volume 2014, Article ID 874102, 11 pages
http://dx.doi.org/10.1155/2014/874102
Research Article

Mechanisms of Laser-Induced Reactions of Stacked Benzene Molecules: A Semiclassical Dynamics Simulation and CASSCF Calculation

1Institute of Bioinformatics, Chongqing University of Posts and Telecommunications, Chongqing 400065, China
2Department of Physical Sciences, Nicholls State University, P.O. Box 2022, Thibodaux, LA 70310, USA

Received 8 May 2014; Accepted 27 June 2014; Published 27 October 2014

Academic Editor: Fuli Li

Copyright © 2014 Kunxian Shu et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. Beukers, A. P. M. Eker, and P. H. M. Lohman, “50 years thymine dimer,” DNA Repair, vol. 7, no. 3, pp. 530–543, 2008. View at Publisher · View at Google Scholar · View at Scopus
  2. C. E. Crespo-Hernández, B. Cohen, and B. Kohler, “Base stacking controls excited-state dynamics in A-T DNA,” Nature, vol. 436, pp. 1141–1144, 2005. View at Publisher · View at Google Scholar
  3. C. T. Middleton, K. de la Harpe, C. Su, Y. K. Law, C. E. Crespo-Hernández, and B. Kohler, “DNA excited-state dynamics: from single bases to the double helix,” Annual Review of Physical Chemistry, vol. 60, pp. 217–239, 2009. View at Publisher · View at Google Scholar
  4. M. Boggio-Pasqua, G. Groenhof, L. V. Schäfer, H. Grubmüller, and M. A. Robb, “Ultrafast deactivation channel for thymine dimerization,” Journal of the American Chemical Society, vol. 129, no. 36, pp. 10996–10997, 2007. View at Publisher · View at Google Scholar · View at Scopus
  5. N. Hoffmann, “Photochemical reactions as key steps in organic synthesis,” Chemical Reviews, vol. 108, pp. 1052–1103, 2008. View at Publisher · View at Google Scholar
  6. U. Streit and C. G. Bochet, “The arene-alkene photocycloaddition,” Beilstein Journal of Organic Chemistry, vol. 7, pp. 525–542, 2011. View at Publisher · View at Google Scholar · View at Scopus
  7. K. E. Wilzbach, J. S. Ritscher, and L. Kaplan, “Benzvalene, the tricyclic valence isomer of benzene,” Journal of the American Chemical Society, vol. 89, no. 4, pp. 1031–1032, 1967. View at Publisher · View at Google Scholar · View at Scopus
  8. L. Kaplan and K. E. Willzbach, “Photolysis of benzene vapor. Benzvalene formation at wavelengths 2537–2370 A,” Journal of the American Chemical Society, vol. 90, no. 12, pp. 3291–3292, 1968. View at Publisher · View at Google Scholar
  9. E. E. van Tamelen and S. P. J. Pappas, “Chemistry of dewar benzene. 1,2,5-Tri-t-butylbicyclo[2.2.0]Hexa-2,5-diene,” Journal of the American Chemical Society, vol. 84, pp. 3789–3791, 1962. View at Publisher · View at Google Scholar
  10. E. E. van Tamelen and S. P. Pappas, “Bicyclo[2.2.0]hexa-2,5-diene [3],” Journal of the American Chemical Society, vol. 85, no. 20, pp. 3297–3298, 1963. View at Publisher · View at Google Scholar · View at Scopus
  11. D. Bryce-Smith, “Orbital symmetry relationships for thermal and photochemical concerted cycloadditions to the benzene ring,” Journal of the Chemical Society D, no. 14, pp. 806–808, 1969. View at Publisher · View at Google Scholar · View at Scopus
  12. J. A. van der Hart, J. J. C. Mulder, and J. Cornelisse, “Funnels and barriers in the photocycloaddition of arenes to alkenes and dienes,” Journal of Photochemistry and Photobiology A, vol. 86, no. 1–3, pp. 141–148, 1995. View at Publisher · View at Google Scholar · View at Scopus
  13. S. Clifford, M. J. Bearpark, F. Bernardi, M. Olivucci, M. A. Robb, and B. R. Smith, “Conical intersection pathways in the photocycloaddition of ethene and benzene: a CASSCF study with MMVB dynamics,” Journal of the American Chemical Society, vol. 118, no. 31, pp. 7353–7360, 1996. View at Publisher · View at Google Scholar · View at Scopus
  14. J. J. Serrano-Pérez, F. de Vleeschouwer, F. de Proft, D. Mendive-Tapia, M. J. Bearpark, and M. A. Robb, “How the conical intersection seam controls chemical selectivity in the photocycloaddition of ethylene and benzene,” Journal of Organic Chemistry, vol. 78, no. 5, pp. 1874–1886, 2013. View at Publisher · View at Google Scholar · View at Scopus
  15. J. J. McCullough, “Photoadditions of aromatic compounds,” Chemical Reviews, vol. 87, no. 4, pp. 811–860, 1987. View at Publisher · View at Google Scholar
  16. D. Döpp, “Photocycloaddition with captodative alkenes,” in Organic, Physical and Materials Photochemistry, V. Ramamurthy and K. S. Schanze, Eds., vol. 6 of Molecular and Supramolecular Photochemistry, pp. 101–148, Marcel Dekker, New York, NY, USA, 2000. View at Google Scholar
  17. K. Mizuno, H. Maeda, A. Sugimoto, and K. Chiyonobu, “Molecular and supramolecular photochemistry,” in Understanding and Manipulating Excited-State Processes, V. Ramamurthy and K. S. Schanze, Eds., vol. 8, p. 127, Marcel Dekker, New York, NY, USA, 2001. View at Google Scholar
  18. D. Döpp, C. Krüger, H. R. Memarian, and Y.-H. Tsay, “1,4-photocycloaddition of α-morpholinoacrylonitrile to 1-acylnaphthalenes,” Angewandte Chemie International Edition in English, vol. 24, no. 12, pp. 1048–1049, 1985. View at Publisher · View at Google Scholar
  19. H. Meier and D. Cao, “Optical switches with biplanemers obtained by intramolecular photocycloaddition reactions of tethered arenes,” Chemical Society Reviews, vol. 42, pp. 143–155, 2013. View at Publisher · View at Google Scholar
  20. A. Y. Rogachev, X.-D. Wen, and R. Hoffmann, “Jailbreaking benzene dimers,” Journal of the American Chemical Society, vol. 134, no. 19, pp. 8062–8065, 2012. View at Publisher · View at Google Scholar
  21. Y. Dou, B. R. Torralva, and R. E. Allen, “Semiclassical electron-radiation-ion dynamics (SERID) and cis-trans photoisomerization of butadiene,” Journal of Modern Optics, vol. 50, no. 15–17, pp. 2615–2643, 2003. View at Publisher · View at Google Scholar · View at Scopus
  22. Y. Dou, B. R. Torralva, and R. E. Allen, “Gas phase absorption spectra and decay of triplet benzene, benzene-d6, and toluene,” Chemical Physics Letters, vol. 392, no. 4, pp. 352–358, 2004. View at Google Scholar
  23. W. Zhang, S. Yuan, A. Li, Y. Dou, J. Zhao, and W. Fang, “Photoinduced thymine dimerization studied by semiclassical dynamics simulation,” The Journal of Physical Chemistry C, vol. 114, no. 12, pp. 5594–5601, 2010. View at Publisher · View at Google Scholar · View at Scopus
  24. S. Yuan, W. Zhang, L. Liu, Y. Dou, W. Fang, and G. V. Lo, “Detailed mechanism for photoinduced cytosine dimerization: a semiclassical dynamics simulation,” The Journal of Physical Chemistry A, vol. 115, no. 46, pp. 13291–13297, 2011. View at Publisher · View at Google Scholar · View at Scopus
  25. M. Ben-Nun and T. J. Martínez, “Ab Initio quantum molecular dynamics,” Advances in Chemical Physics, vol. 121, pp. 439–512, 2002. View at Google Scholar
  26. W. Domcke, D. R. Yarkony, and H. Koppel, Eds., Conical Intersections: Electronic Structure, Dynamics, and Spectroscopy, World Scientific, Singapore, 2004.
  27. M. Baer, Beyond Born-Oppenheimer: Electronic Nonadiabatic Coupling Terms and Conical Intersections, Wiley-Interscience, Hoboken, NJ, USA, 2006.
  28. M. J. Bearpark, F. Bernardi, S. Clifford, M. Olivucci, M. A. Robb, and T. J. Vreven, “The lowest energy excited singlet states and the cis-trans photoisomerization of styrene,” Journal of the American Chemical Society, vol. 101, no. 2, pp. 3841–3847, 1997. View at Google Scholar
  29. B. G. Levine and T. J. Martínez, “Isomerization through conical intersections,” Annual Review of Physical Chemistry, vol. 58, pp. 613–634, 2007. View at Publisher · View at Google Scholar
  30. J. Frank, Introduction to Computational Chemistry, John Wiley & Sons, Chichester, UK, 2007.
  31. C. J. Cramer, Essentials of Computational Chemistry, John Wiley & Sons, Chichester, UK, 2002.
  32. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., Gaussian 09, Revision D01, Gaussian, Wallingford, Conn, USA, 2010.
  33. S. Tsuzuki, “Interactions with aromatic rings,” Structure and Bonding, vol. 115, pp. 149–193, 2005. View at Publisher · View at Google Scholar · View at Scopus
  34. K. C. Janda, J. C. Hemminger, J. S. Winn, S. E. Novick, S. J. Harris, and W. Klemperer, “Benzene dimer: a polar molecule,” The Journal of Chemical Physics, vol. 63, no. 4, pp. 1419–1421, 1975. View at Publisher · View at Google Scholar · View at Scopus
  35. J. M. Steed, T. A. Dixon, and W. Klemperer, “Molecular beam studies of benzene dimer, hexafluorobenzene dimer, and benzene-hexafluorobenzene,” The Journal of Chemical Physics, vol. 70, no. 11, pp. 4940–4946, 1979. View at Publisher · View at Google Scholar · View at Scopus
  36. E. Arunan and H. S. Gutowsky, “The rotational spectrum, structure and dynamics of a benzene dimer,” The Journal of Chemical Physics, vol. 98, no. 5, pp. 4294–4296, 1993. View at Publisher · View at Google Scholar · View at Scopus
  37. W. Scherzer, O. Kratzschmar, H. L. Selzle, and E. W. Schlag, “Structural isomers of the benzene dimer from mass selective hole-burning spectroscopy,” Zeitschrift für Naturforschung A, vol. 47, pp. 1248–1252, 1992. View at Google Scholar