Table of Contents Author Guidelines Submit a Manuscript
International Journal of Photoenergy
Volume 2014 (2014), Article ID 597165, 11 pages
http://dx.doi.org/10.1155/2014/597165
Research Article

Detailed Photoisomerization Dynamics of a Green Fluorescent Protein Chromophore Based Molecular Switch

1MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter and Department of Applied Physics, Xi’an Jiaotong University, Xi’an 710049, China
2Department of Physics, Hubei University, Wuhan 430062, China

Received 25 April 2014; Accepted 16 July 2014; Published 3 September 2014

Academic Editor: Yusheng Dou

Copyright © 2014 Chen-Wei Jiang 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. D. H. Waldeck, “Photoisomerization dynamics of stilbenes,” Chemical Reviews, vol. 91, no. 3, pp. 415–438, 1991. View at Publisher · View at Google Scholar · View at Scopus
  2. T. Baumert, T. Frohnmeyer, B. Kiefer et al., “Femtosecond transition state dynamics of cis-stilbene,” Applied Physics B: Lasers and Optics, vol. 72, no. 1, pp. 105–108, 2001. View at Publisher · View at Google Scholar · View at Scopus
  3. W. Fuß, C. Kosmidis, W. E. Schmid, and S. A. Trushin, “The photochemical cis-trans isomerization of free stilbene molecules follows a hula-twist pathway,” Angewandte Chemie, vol. 43, no. 32, pp. 4178–4182, 2004. View at Publisher · View at Google Scholar · View at Scopus
  4. Y. Ishibashi, M. Murakami, H. Miyasaka, S. Kobatake, M. Irie, and Y. Yokoyama, “Laser multiphoton-gated photochromic reaction of a fulgide derivative,” Journal of Physical Chemistry C, vol. 111, no. 6, pp. 2730–2737, 2007. View at Publisher · View at Google Scholar · View at Scopus
  5. T. Cordes, S. Malkmus, J. A. DiGirolamo et al., “Accelerated and efficient photochemistry from higher excited electronic states in fulgide molecules,” The Journal of Physical Chemistry A, vol. 112, no. 51, pp. 13364–13371, 2008. View at Publisher · View at Google Scholar · View at Scopus
  6. F. Renth, R. Siewertsen, and F. Temps, “Enhanced photoswitching and ultrafast dynamics in structurally modified photochromic fulgides,” International Reviews in Physical Chemistry, vol. 32, no. 1, pp. 1–38, 2013. View at Publisher · View at Google Scholar · View at Scopus
  7. M. Takeshita and M. Irie, “Photoresponsive tweezers for alkali metal ions. Photochromic diarylethenes having two crown ether moieties,” Journal of Organic Chemistry, vol. 63, no. 19, pp. 6643–6649, 1998. View at Publisher · View at Google Scholar · View at Scopus
  8. S. F. Yan, V. N. Belov, M. L. Bossi, and S. W. Hell, “Switchable fluorescent and solvatochromic molecular probes based on 4-amino-N-methylphthalimide and a photochromic diarylethene,” European Journal of Organic Chemistry, vol. 2008, no. 15, pp. 2531–2538, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. Y. Li and Q. Li, “Photochemically reversible and thermally stable axially chiral diarylethene switches,” Organic Letters, vol. 14, no. 17, pp. 4362–4365, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. I. K. Lednev, T.-Q. Ye, L. C. Abbott, R. E. Hester, and J. N. Moore, “Photoisomerization of a capped azobenzene in solution probed by ultrafast time-resolved electronic absorption spectroscopy,” The Journal of Physical Chemistry A, vol. 102, no. 46, pp. 9161–9166, 1998. View at Google Scholar · View at Scopus
  11. T. Fujino and T. Tahara, “Picosecond time-resolved Raman study of trans-azobenzene,” Journal of Physical Chemistry A, vol. 104, no. 18, pp. 4203–4210, 2000. View at Publisher · View at Google Scholar · View at Scopus
  12. H. Satzger, S. Spörlein, C. Root, J. Wachtveitl, W. Zinth, and P. Gilch, “Fluorescence spectra of trans- and cis-azobenzene: emission from the Franck-Condon state,” Chemical Physics Letters, vol. 372, no. 1-2, pp. 216–223, 2003. View at Publisher · View at Google Scholar · View at Scopus
  13. I. Conti, M. Garavelli, and G. Orlandi, “The different photoisomerization efficiency of azobenzene in the lowest nπ and ππ singlets: the role of a phantom state,” Journal of the American Chemical Society, vol. 130, no. 15, pp. 5216–5230, 2008. View at Publisher · View at Google Scholar · View at Scopus
  14. C.-W. Jiang, R.-H. Xie, F.-L. Li, and R. E. Allen, “Comparative studies of the trans—Cis photoisomerizations of azobenzene and a bridged azobenzene,” Journal of Physical Chemistry A, vol. 115, no. 3, pp. 244–249, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. H.-H. Liu, X. Zhang, Z. Gao, and Y. Chen, “Photoconversion of a protonated diarylethene derivative,” Journal of Physical Chemistry A, vol. 116, no. 40, pp. 9900–9903, 2012. View at Publisher · View at Google Scholar · View at Scopus
  16. G. Haberhauer and C. Kaliweit, “A bridged azobenzene derivative as a reversible, light-induced chirality switch,” Angewandte Chemie, vol. 49, no. 13, pp. 2418–2421, 2010. View at Publisher · View at Google Scholar · View at Scopus
  17. I. K. Lednev, T.-Q. Ye, P. Matousek et al., “Femtosecond time-resolved UV-visible absorption spectroscopy of trans-azobenzene: dependence on excitation wavelength,” Chemical Physics Letters, vol. 290, no. 1–3, pp. 68–74, 1998. View at Publisher · View at Google Scholar · View at Scopus
  18. T. Pancur, F. Renth, F. Temps et al., “Femtosecond fluorescence up-conversion spectroscopy of a rotation-restricted azobenzene after excitation to the S1 state,” Physical Chemistry Chemical Physics, vol. 7, no. 9, pp. 1985–1989, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. R. Siewertsen, H. Neumann, B. Buchheim-Stehn et al., “Highly efficient reversible Z-E photoisomerization of a bridged azobenzene with visible light through resolved S1(npi*) absorption bands,” Journal of the American Chemical Society, vol. 131, no. 43, pp. 15594–15595, 2009. View at Publisher · View at Google Scholar · View at Scopus
  20. M. Chalfie, Y. Tu, G. Euskirchen, W. W. Ward, and D. C. Prasher, “Green fluorescent protein as a marker for gene expression,” Science, vol. 263, no. 5148, pp. 802–805, 1994. View at Publisher · View at Google Scholar · View at Scopus
  21. V. Voliani, R. Bizzarri, R. Nifosì et al., “Cis-trans photoisomerization of fluorescent-protein chromophores,” The Journal of Physical Chemistry B, vol. 112, no. 34, pp. 10714–10722, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. S. Rafiq, B. K. Rajbongshi, N. N. Nair, P. Sen, and G. Ramanathan, “Excited state relaxation dynamics of model green fluorescent protein chromophore analogs: Evidence for cis-trans isomerism,” Journal of Physical Chemistry A, vol. 115, no. 47, pp. 13733–13742, 2011. View at Publisher · View at Google Scholar · View at Scopus
  23. J.-S. Yang, G.-J. Huang, Y.-H. Liu, and S.-M. Peng, “Photoisomerization of the green fluorescence protein chromophore and the meta- and para-amino analogues,” Chemical Communications, vol. 2008, no. 11, pp. 1344–1346, 2008. View at Publisher · View at Google Scholar · View at Scopus
  24. P. Naumov, J. Kowalik, K. M. Solntsev et al., “Topochemistry and photomechanical effects in crystals of green fluorescent protein-like chromophores: Effects of hydrogen bonding and crystal packing,” Journal of the American Chemical Society, vol. 132, no. 16, pp. 5845–5857, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. X. He, A. F. Bell, and P. J. Tonge, “Synthesis and spectroscopic studies of model red fluorescent protein chromophores,” Organic Letters, vol. 4, no. 9, pp. 1523–1526, 2002. View at Publisher · View at Google Scholar · View at Scopus
  26. A. Kikuchi, E. Fukumura, S. Karasawa, H. Mizuno, A. Miyawaki, and Y. Shiro, “Structural characterization of a thiazoline-containing chromophore in an orange fluorescent protein, monomeric kusabira orange,” Biochemistry, vol. 47, no. 44, pp. 11573–11580, 2008. View at Publisher · View at Google Scholar · View at Scopus
  27. M. Blanco-Lomas, P. J. Campos, and D. Sampedro, “Benzylidene-oxazolones as molecular photoswitches,” Organic Letters, vol. 14, no. 17, pp. 4334–4337, 2012. View at Publisher · View at Google Scholar · View at Scopus
  28. 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
  29. R. E. Allen, T. Dumitrica, and B. Torralva, “Electronic and structural response of materials to fast intense laser pulses,” in Ultrafast Physical Processes in Semiconductors, K. T. Tsen, Ed., chapter 7, Academic Press, New York, NY, USA, 2001. View at Google Scholar
  30. R. E. Allen, “Electron-ion dynamics: a technique for simulating both electronic transitions and ionic motion in molecules and materials,” Physical Review B, vol. 50, no. 24, pp. 18629–18632, 1994. View at Publisher · View at Google Scholar · View at Scopus
  31. R. E. Allen, “Coupling of electrons to the electromagnetic field in a localized basis,” Physical Review B, vol. 78, no. 6, Article ID 064305, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. R. E. Allen, T. Dumitrică, and B. Torralva, Ultrafast Physical Processes in Semiconductors, chapter 7, Academic Press, New York, NY, USA, 2001, edited by K. T. Tsen.
  33. D. Porezag, T. Frauenheim, T. Köhler, G. Seifert, and R. Kaschner, “Construction of tight-binding-like potentials on the basis of density-functional theory: application to carbon,” Physical Review B, vol. 51, no. 19, pp. 12947–12957, 1995. View at Publisher · View at Google Scholar · View at Scopus
  34. G. Seifert, D. Porezag, and T. Frauenheim, “Calculations of molecules, clusters, and solids with a simplified LCAO-DFT-LDA scheme,” International Journal of Quantum Chemistry, vol. 58, no. 2, pp. 185–192, 1996. View at Publisher · View at Google Scholar · View at Scopus
  35. Y. Dou and R. E. Allen, “Detailed dynamics of a complex photochemical reaction: Cis-trans photoisomerization of stilbene,” The Journal of Chemical Physics, vol. 119, no. 20, pp. 10658–10666, 2003. View at Publisher · View at Google Scholar · View at Scopus
  36. Y. Dou, B. R. Torralva, and R. E. Allen, “Interplay of electronic and nuclear degrees of freedom in a femtosecond-scale photochemical reaction,” Chemical Physics Letters, vol. 392, no. 4–6, pp. 352–357, 2004. View at Publisher · View at Google Scholar · View at Scopus
  37. P. Sauer and R. E. Allen, “Dynamics of the photoinduced ring-opening of stilbene, a prototypical diarylethene,” Chemical Physics Letters, vol. 434, no. 4-6, pp. 260–264, 2007. View at Publisher · View at Google Scholar · View at Scopus
  38. P. Sauer and R. E. Allen, “Influence of laser pulse parameters on dynamical processes during azobenzene photoisomerization,” Journal of Physical Chemistry A, vol. 112, no. 44, pp. 11142–11152, 2008. View at Publisher · View at Google Scholar · View at Scopus
  39. C.-W. Jiang, R.-H. Xie, F.-L. Li, and R. E. Allen, “Photocyclization of trans-stilbene induced by an ultrafast laser pulse,” Chemical Physics Letters, vol. 487, no. 4–6, pp. 177–182, 2010. View at Publisher · View at Google Scholar · View at Scopus
  40. C. Jiang, R. Xie, F. Li, and R. E. Allen, “Trans-to-cis isomerization of stilbene following an ultrafast laser pulse,” Chemical Physics Letters, vol. 474, no. 4–6, pp. 263–267, 2009. View at Publisher · View at Google Scholar · View at Scopus
  41. C.-W. Jiang, R.-H. Xie, F.-L. Li, and R. E. Allen, “Ultrafast cis-to-trans photoisomerization of a bridged azobenzene through nπ excitation: rotational pathway is not restricted,” Chemical Physics Letters, vol. 521, pp. 107–112, 2012. View at Publisher · View at Google Scholar · View at Scopus
  42. Y. Dou, Y. Lei, A. Li et al., “Detailed dynamics of the photodissociation of cyclobutane,” The Journal of Physical Chemistry A, vol. 111, no. 6, pp. 1133–1137, 2007. View at Publisher · View at Google Scholar · View at Scopus
  43. W. Zhang, S. Yuan, A. Li, Y. Dou, J. Zhao, and W. Fang, “Photoinduced thymine dimerization studied by semiclassical dynamics simulation,” Journal of Physical Chemistry C, vol. 114, no. 12, pp. 5594–5601, 2010. View at Publisher · View at Google Scholar · View at Scopus
  44. S. Yuan, W. Zhang, L. Liu, Y. Dou, W. Fang, and G. V. Lo, “Detailed mechanism for photoinduced cytosine dimerization: a semiclassical dynamics simulation,” Journal of Physical Chemistry A, vol. 115, no. 46, pp. 13291–13297, 2011. View at Publisher · View at Google Scholar · View at Scopus
  45. E. Teller, “The crossing of potential surfaces,” The Journal of Physical Chemistry, vol. 41, no. 1, pp. 109–116, 1937. View at Publisher · View at Google Scholar · View at Scopus
  46. M. Baer, Beyond Born-Oppenheimer: Electronic Nonadiabatic Coupling Terms and Conical Intersections, Wiley-Interscience, Hoboken, NJ, USA, 2006. View at Publisher · View at Google Scholar · View at MathSciNet
  47. C. Nonnenberg, H. Gaub, and I. Frank, “First-principles simulation of the photoreaction of a capped azobenzene: the rotational pathway is feasible,” ChemPhysChem, vol. 7, no. 7, pp. 1455–1461, 2006. View at Publisher · View at Google Scholar · View at Scopus
  48. Y. Norikane and N. Tamaoki, “Photochemical and thermal cis/trans isomerization of cyclic and noncyclic azobenzene dimers: effect of a cyclic structure on isomerization,” European Journal of Organic Chemistry, no. 5, pp. 1296–1302, 2006. View at Publisher · View at Google Scholar · View at Scopus
  49. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., GAUSSIAN, Inc., Wallingford, CT, 2004.