Substituent-controlled photoisomerization in retinal chromophore models: Fluorinated and methoxy-substituted protonated Schiff bases

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 190, Issue 2-3, 2007, Pages 258-273

  Conti, Irene ^a   Garavelli, Marco ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

CASPT2 CASSCF; Conical intersections; Photoisomerization; Retinal; Substitution

Indexed keywords

EID: 34447627177     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2006.12.006     Document Type: Article

References (35)

1. Wald G. Science 162 (1968) 230-239
2. Needleman R. In: Horspool W.M., and Song P.-S. (Eds). CRC Handbook of Organic Photochemistry and Photobiology vol. (1995), CRC Press, Boca Raton, FL 1508-1515
3. Sugihara M., Hufen J., and Buss V. Biochemistry 45 (2006) 801-810
4. Vogel R., Siebert F., Yan E.C.Y., Sakmar T.P., Hirshfeld A., and Sheves M. J. Am. Chem. Soc. 128 (2006) 10503-10512
5. Nakamichi H., and Okada T. Proc. Natl. Acad. Sci. 103 (2006) 12729-12734
6. Kandori H., Shichida Y., and Yoshizawa T. Biochemistry (Moscow) 66 (2001) 1197-1209
7. Mathies R., and Lugtenburg J. In: Stavenga D.G., DeGrip W.J., and Pugh E.N.J. (Eds). Molecular Mechanism of Vision vol. 3 (2000), Elsevier Science Press, New York 55-90
8. Migani A., Sinicropi A., Ferré N., Cembran A., Garavelli M., and Olivucci M. Faraday Discuss. 127 (2004) 179-191
9. Fujimoto K., Hasegawa J.-Y., Hayashi S., Kato S., and Nakatsuji H. Chem. Phys. Lett. 414 (2005) 239-242
10. Andruniow T., Ferré N., and Olivucci M. Proc. Natl. Acad. Sci. 101 (2004) 17908-17913
11. Cembran A., Gonzáles-Luque R., Altoè P., Merchán M., Bernardi F., Olivucci M., and Garavelli M. J. Phys. Chem. A 109 (2005) 6597-6605
12. Garavelli M., Vreven T., Celani P., Bernardi F., Robb M.A., and Olivucci M. J. Am. Chem. Soc. 120 (1998) 1285-1288
13. Cembran A., Bernardi F., Olivucci M., and Garavelli M. Proc. Natl. Acad. Sci. 102 (2005) 6255-6260
14. Sekharan S., Weingart, and Buss V. Biophys. J. 91 (2006) L07-L09
15. Cembran A., Bernardi F., Olivucci M., and Garavelli M. J. Am. Chem. Soc. 126 (2004) 16018-16037
16. González-Luque R., Garavelli M., Bernardi F., Merchán M., Robb M.A., and Olivucci M. Proc. Natl. Acad. Sci. USA 97 (2000) 9379-9384
17. De Vico L., Page C.S., Garavelli M., Bernardi F., Basosi R., and Olivucci M. J. Am. Chem. Soc. 124 (2002) 4124-4134
18. Garavelli M., Celani P., Bernardi F., Robb M.A., and Olivucci M. J. Am. Chem. Soc. 119 (1997) 6891-6901
19. Garavelli M., Bernardi F., Olivucci M., Vreven T., Klein S., Celani P., and Robb M.A. Faraday Discuss. 110 (1998) 51-70
20. De Vico L., Garavelli M., Bernardi F., and Olivucci M. J. Am. Chem. Soc. 127 (2005) 2433-2442
21. Gilbert A., and Baggott J. Essentials of Molecular Photochemistry (1991), Blackwell Science, Oxford
22. Turro N.J. Modern Molecular Photochemistry (1991), Benjamin-Cummings, Menlo Park, CA
23. Hamm P., Zurek M., Roschinger T., Patzelt H., Oesterhelt D., and Zinth W. Chem. Phys. Lett. 263 (1996) 613-621
24. Kandori H., Sasabe H., Nakanishi K., Yoshizawa T., Mizukami T., and Shichida Y. J. Am. Chem. Soc. 118 (1996) 1002-1005
25. Schoenlein R.W., Peteanu L.A., Mathies R.A., and Shank C.V. Science 254 (1991) 412-415
26. Mathies R.A., Cruz C.H.B., Pollard W.T., and Shank C.V. Science 240 (1988) 777-779
27. Dartnall H.J.A. Vision Res. 8 (1968) 339-358
28. Martinez T.J. Accounts Chem. Res. 39 (2006) 119-126
29. Francesch A., Alvarez R., Lopez S., and De Lera A.R. J. Org. Chem. 62 (1997) 310-319
30. Albeck A., Friedman N., Sheves M., and Ottolenghi M. Biophys. J. 56 (1989) 1259-1265
31. Conti I., Bernardi F., Orlandi G., and Garavelli M. Mol. Phys. 104 (2006) 915-924
32. Celani P., Robb M.A., Garavelli M., Bernardi F., and Olivucci M. Chem. Phys. Lett. 243 (1995) 1-8
33. Bearpark M.J., Robb M.A., and Bernhard Schlegel H. Chem. Phys. Lett. 223 (1994) 269-274
34. Andersson K., Barysz M., Bernhardsson A., Blomberg M.R.A., Cooper D.L., Fülscher M.P., Graaf C.D., Hess B.A., Karlström G., Lindh R., Malmqvist P.-A., Nakajima T., Neogrády P., Olsen J., Roos B.O., Schimmelpfennig B., Schütz M., Seijo L., Serrano-Andrés L., Siegbahn P.E.M., Stålring J., Thorsteinsson T., Veryazov V., and Widmark P.-O. MOLCAS, Version 5.4 (2002), Lund University, Sweden
35. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A.J., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., 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., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., and Pople J.A. Gaussian 98, Revision A.7 (1998), Gaussian, Inc., Pittsburgh PA