Remarkable acceleration for back-reaction of a fast photochromic molecule

Journal of Physical Chemistry Letters

Volumn 1, Issue 7, 2010, Pages 1112-1115

  Harada, Yuka ^a   Hatano, Sayaka ^a   Kimoto, Atsushi ^a   Abe, Jiro ^a  

^a AOYAMA GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[2.2]PARACYCLOPHANE; MARCUS THEORY; PHOTOCHROMIC MOLECULES; ROOM TEMPERATURE; SINGLE BOND; UV-LIGHT IRRADIATION;

PHOTOCHROMISM;

EID: 77950568812     PISSN: None     EISSN: 19487185     Source Type: Journal    
DOI: 10.1021/jz100228w     Document Type: Article

References (24)

1. Crano, J. C.; Guglielmetti, R. J. Organic Photochromic and Thermochromic Compounds; Plenum Press: New York, 1999.
2. Duerr, H.; Bouas-Laurent, H. Photochromism: Molecules and Systems; Elsevier: Amsterdam, The Netherlands, 2003.
3. Amimoto, K.; Kawato, T. Photochromism of Organic Compounds in the Crystal State J. Photochem. Photobiol., C 2005, 6, 207 - 226
4. Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
5. Raymo, F. M.; Tomasulo, M. Optical Processing with Photochromic Switches Chem. - Eur. J. 2006, 12, 3186 - 3193
6. Fujita, K.; Hatano, S.; Kato, D.; Abe, J. Photochromism of a Radical Diffusion-Inhibited Hexaarylbiimidazole Derivative with Intense Coloration and Fast Decoloration Performance Org. Lett. 2008, 10, 3105 - 3108
7. Kishimoto, Y.; Abe, J. A Fast Photochromic Molecule That Colors Only under UV Light J. Am. Chem. Soc. 2009, 131, 4227 - 4229
8. Hayashi, T.; Maeda, K. Preparation of a New Phototropic Substance Bull. Chem. Soc. Jpn. 1960, 33, 565 - 567
9. Kimoto, A.; Niitsu, S.; Iwahori, F.; Abe, J. Formation of Hexaarylbiimidazole Heterodimers via the Cross Recombination of Two Lophyl Radicals New J. Chem. 2009, 33, 1339 - 1342
10. Hatano, S.; Abe, J. Activation Parameters for the Recombination Reaction of Intramolecular Radical Pairs Generated from the Radical Diffusion-Inhibited HABI Derivative J. Phys. Chem. A. 2008, 112, 6098 - 6103
11. Iwahori, F.; Hatano, S.; Abe, J. Rational Design of a New Class of Diffusion-Inhibited HABI with Fast Back-Reaction J. Phys. Org. Chem. 2007, 20, 857 - 863
12. Kikuchi, A.; Iwahori, F.; Abe, J. Definitive Evidence for the Contribution of Biradical Character in a Closed-Shell Molecule, Derivative of 1,4-Bis-(4,5-diphenylimidazol-2-ylidene)cyclohexa-2,5-diene J. Am. Chem. Soc. 2004, 126, 6526 - 6527
13. Abe, J.; Sano, T.; Kawano, M.; Ohashi, Y.; Matsushita, M. M.; Iyoda, T. EPR and Density Functional Studies of Light-Induced Radical Pairs in a Single Crystal of a Hexaarylbiimidazolyl Derivative Angew. Chem., Int. Ed. 2001, 40, 580 - 582 (Pubitemid 32144469)
14. Kawano, M.; Sano, T.; Abe, J.; Ohashi, Y. The First in Situ Direct Observation of the Light-Induced Radical Pair from a Hexaarylbiimidazolyl Derivative by X-ray Crystallography J. Am. Chem. Soc. 1999, 121, 8106 - 8107
15. Marcus, R. A. On the Theory of Oxidation-Reduction Reactions Involving Electron Transfer. I J. Chem. Phys. 1956, 24, 966 - 978
16. Marcus, R. A. Chemical and Electrochemical Electron-Transfer Theory Annu. Rev. Phys. Chem. 1964, 15, 155 - 196
17. Marcus, R. A. Theoretical Relations among Rate Constants, Barriers, and Brønsted Slopes of Chemical Reactions J. Phys. Chem. 1968, 72, 891 - 899
18. Marcus, R. A. Unusual Slopes of Free Energy Plots in Kinetics J. Am. Chem. Soc. 1969, 91, 7224 - 7225
19. Cohen, A. O.; Marcus, R. A. Slope of Free Energy Plots in Chemical Kinetics J. Phys. Chem. 1968, 72, 4249 - 4256
20. Alabugin, I. V.; Manoharan, M.; Breiner, B.; Lewis, F. D. Control of Kinetics and Thermodynamics of [1,5]-Shifts by Aromaticity: A View through the Prism of Marcus Theory J. Am. Chem. Soc. 2003, 125, 9329 - 9342
21. Chen, X.; Brauman, J. I. Hydrogen Bonding Lowers Intrinsic Nucleophilicity of Solvated Nucleophiles J. Am. Chem. Soc. 2008, 130, 15038 - 15046
22. Miyasaka, H.; Satoh, Y.; Ishibashi, Y.; Ito, S.; Nagasawa, Y.; Taniguchi, S.; Chosrowjan, H.; Mataga, N.; Kato, D.; Kikuchi, A.; Abe, J. Ultrafast Photodissociation Dynamics of a Hexaarylbiimidazole Derivative with Pyrenyl Groups: Dispersive Reaction from Femtosecond to 10 ns Time Regions J. Am. Chem. Soc. 2009, 131, 7256 - 7263
23. Zhao, Y.; Schultz, N. E.; Truhlar, D. G. Design of Density Functionals by Combining the Method of Constraint Satisfaction with Parametrization for Thermochemistry, Thermochemical Kinetics, and Noncovalent Interactions J. Chem. Theory Comput. 2006, 2, 364 - 382
24. Zhao, Y.; Truhlar, D. G. How Well Can New-Generation Density Functionals Describe the Energetics of Bond-Dissociation Reactions Producing Radicals? J. Phys. Chem. A 2008, 112, 1095 - 1099