Ultrafast Cspiro-O dissociation via a conical intersection drives spiropyran to merocyanine photoswitching

Journal of Physical Chemistry A

Volumn 118, Issue 8, 2014, Pages 1339-1349

  Prager, Stefan ^a,b   Burghardt, Irene ^b   Dreuw, Andreas ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BOND DISSOCIATION; CONICAL INTERSECTION; FIRST EXCITED STATE; FRANCK-CONDON; GROUND-STATE ENERGIES; PHOTOCHEMICAL CONVERSION; PHOTOSWITCHING; TWO-DIMENSIONAL SCAN;

DISSOCIATION; EXCITED STATES; GROUND STATE; QUANTUM CHEMISTRY; TORSIONAL STRESS;

PHOTOCHROMISM;

EID: 84897644685     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp4088942     Document Type: Article

References (64)

1. Feringa, B. L.; Browne, W. R. Molecular switches, 2 nd ed.; Wiley-VCH: Weinheim, 2011.
2. Crano, J. C.; Guglielmetti, R. J. Organic photochromic and thermochromic compounds: Vol. 1: Main Photochromic Families; Kluwer Academic: New York, 1999.
3. Crano, J. C.; Guglielmetti, R. J. Organic photochromic and thermochromic compounds: Vol. 2: Physiochemical Studies, Biological Applications and Thermochromism; Kluwer Academic/Plenum Publishers: New York, 1999.
4. Dürr, H.; Bouas-Laurent, H. Photochromism: Molecules and systems, revised ed.; Elsevier: Amsterdam and Boston, 2003.
5. Khan, A.; Kaiser, C.; Hecht, S. Prototype of a Photoswitchable Foldamer Angew. Chem., Int. Ed. 2006, 45, 1878-1881
6. Cattaneo, P.; Persico, M. An ab initio study of the photochemistry of azobenzene Phys. Chem. Chem. Phys. 1999, 1, 4739-4743
7. ZalesŚny, R.; Matczyszyn, K.; Kaczmarek, A.; Bartkowiak, W.; Cysewski, P. Experimental and theoretical investigations of spectroscopic properties of azobenzene derivatives in solution J. Mol. Model. 2007, 13, 785-791
8. Sauer, P.; Allen, R. E. Influence of Laser Pulse Parameters on Dynamical Processes during Azobenzene Photoisomerization J. Phys. Chem. A 2008, 112, 11142-11152
9. Ho, J.-W.; Chen, W.-K.; Cheng, P.-Y. Femtosecond pump-probe photoionization-photofragmentation spectroscopy: Photoionization-induced twisting and coherent vibrational motion of azobenzene cation J. Chem. Phys. 2009, 131, 134308
10. Beharry, A. A.; Woolley, G. A. Azobenzene photoswitches for biomolecules Chem. Soc. Rev. 2011, 40, 4422
11. Bandara, H. M. D.; Burdette, S. C. Photoisomerization in different classes of azobenzene Chem. Soc. Rev. 2012, 41, 1809
12. Heller, H. G.; Oliver, S. Photochromic heterocyclic fulgides. Part 1. Rearrangement reactions of (E)-α-3-furylethylidene(isopropylidene)succinic anhydride J. Chem. Soc., Perkin Trans. 1 1981, 197
13. Darcy, P. J.; Heller, H. G.; Strydom, P. J.; Whittall, J. Photochromic heterocyclic fulgides. Part 2. Electrocyclic reactions of (E)-α-2,5- dimethyl-3-furylethylidene(alkyl-substituted methylene)succinic anhydrides J. Chem. Soc., Perkin Trans. 1 1981, 202
14. Krysanov, S.; Alfimov, M. Ultrafast formation of transients in spiropyran photochromism Chem. Phys. Lett. 1982, 91, 77-80
15. Ernsting, N. P. Transient optical absorption spectroscopy of the photochemical spiropyran-merocyanine conversion Chem. Phys. Lett. 1989, 159, 526-531
16. Ernsting, N. P.; Dick, B.; Arthen-Engeland, T. The primary photochemical reaction step of unsubstituted indolino-spiropyrans Pure Appl. Chem. 1990, 62, 1483-1488
17. Favaro, G.; Malatesta, V.; Mazzucato, U.; Ottavi, G.; Romani, A. Thermally reversible photoconversion of spiroindoline-naphtho-oxazines to photomerocyanines: a photochemical and kinetic study J. Photochem. Photobiol., A 1995, 87, 235-241
18. Rini, M.; Holm, A.-K.; Nibbering, E. T. J.; Fidder, H. Ultrafast UV-mid-IR Investigation of the Ring Opening Reaction of a Photochromic Spiropyran J. Am. Chem. Soc. 2003, 125, 3028-3034
19. Celani, P.; Bernardi, F.; Olivucci, M.; Robb, M. A. Conical Intersection Mechanism for Photochemical Ring Opening in Benzospiropyran Compounds J. Am. Chem. Soc. 1997, 119, 10815-10820
20. Cottone, G.; Noto, R.; La Manna, G. Theoretical study of spiropyran-merocyanine thermal isomerization Chem. Phys. Lett. 2004, 388, 218-222
21. Marta, S.-L.; Carlos Manuel, E.; Jose, H.-R.; Luis, S.-A. Ultrafast Ring-Opening/Closing and Deactivation Channels for a Model Spiropyran- Merocyanine System J. Phys. Chem. A 2011, 115, 9128-9138
22. Migani, A.; Gentili, P. L.; Negri, F.; Olivucci, M.; Romani, A.; Favaro, G.; Becker, R. S. The Ring-Opening Reaction of Chromenes: A Photochemical Mode-Dependent Transformation J. Phys. Chem. A 2005, 109, 8684-8692
23. Pople, J. A.; Seeger, R.; Krishnan, R. Variational configuration interaction methods and comparison with perturbation theory Int. J. Quantum Chem. 1977, 12, 149-163
24. Head-Gordon, M.; Rico, R. J.; Oumi, M.; Lee, T. J. A doubles correction to electronic excited states from configuration interaction in the space of single substitutions Chem. Phys. Lett. 1994, 219, 21-29
25. Christiansen, O.; Koch, H.; Jørgensen, P. The second-order approximate coupled cluster singles and doubles model CC2 Chem. Phys. Lett. 1995, 243, 409-418
26. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98, 5648
27. Becke, A. D. A new mixing of Hartree-Fock and local density-functional theories J. Chem. Phys. 1993, 98, 1372
28. Chai, J.-D.; Head-Gordon, M. Systematic optimization of long-range corrected hybrid density functionals J. Chem. Phys. 2008, 128, 084106
29. Chai, J.-D.; Head-Gordon, M. Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections Phys. Chem. Chem. Phys. 2008, 10, 6615-6620
30. Yanai, T.; Tew, D. P.; Handy, N. C. A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP) Chem. Phys. Lett. 2004, 393, 51-57
31. Tawada, Y.; Tsuneda, T.; Yanagisawa, S.; Yanai, T.; Hirao, K. A long-range-corrected time-dependent density functional theory J. Chem. Phys. 2004, 120, 8425
32. Vydrov, O. A.; Scuseria, G. E. Assessment of a long-range corrected hybrid functional J. Chem. Phys. 2006, 125, 234109
33. Vydrov, O. A.; Heyd, J.; Krukau, A. V.; Scuseria, G. E. Importance of short-range versus long-range Hartree-Fock exchange for the performance of hybrid density functionals J. Chem. Phys. 2006, 125, 074106
34. Schäfer, A.; Horn, H.; Ahlrichs, R. Fully optimized contracted Gaussian basis sets for atoms Li to Kr J. Chem. Phys. 1992, 97, 2571
35. Schäfer, A.; Huber, C.; Ahlrichs, R. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr J. Chem. Phys. 1994, 100, 5829
36. Weigend, F.; Häser, M.; Patzelt, H.; Ahlrichs, R. RI-MP2: optimized auxiliary basis sets and demonstration of efficiency Chem. Phys. Lett. 1998, 294, 143-152
37. Dunning, T. H. Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen J. Chem. Phys. 1989, 90, 1007
38. Kendall, R. A.; Dunning, T. H.; Harrison, R. J. Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions J. Chem. Phys. 1992, 96, 6796
39. Woon, D. E.; Dunning, T. H. Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon J. Chem. Phys. 1993, 98, 1358
40. Hättig, C.; Weigend, F. CC2 excitation energy calculations on large molecules using the resolution of the identity approximation J. Chem. Phys. 2000, 113, 5154
41. Eichkorn, K.; Treutler, O.; Öhm, H.; Häser, M.; Ahlrichs, R. Auxiliary basis sets to approximate Coulomb potentials Chem. Phys. Lett. 1995, 240, 283-290
42. Eichkorn, K.; Weigend, F.; Treutler, O.; Ahlrichs, R. Auxiliary basis sets for main row atoms and transition metals and their use to approximate Coulomb potentials Theor. Chem. Acc. 1997, 97, 119-124
43. Levine, B. G.; Coe, J. D.; Martínez, T. J. Optimizing Conical Intersections without Derivative Coupling Vectors: Application to Multistate Multireference Second-Order Perturbation Theory (MS-CASPT2) J. Phys. Chem. B 2008, 112, 405-413
44. Sicilia, F.; Blancafort, L.; Bearpark, M. J.; Robb, M. A. New Algorithms for Optimizing and Linking Conical Intersection Points J. Chem. Theory Comput. 2008, 4, 257-266
45. Minezawa, N.; Gordon, M. S. Optimizing Conical Intersections by SpinaîĹŠFlip Density Functional Theory: Application to Ethylene. J. Phys. Chem. A 2009, 113, 12749-12753, PMID: 19905013.
46. Xu, X.; Gozem, S.; Olivucci, M.; Truhlar, D. G. Combined Self-Consistent-Field and Spin-Flip Tamm-Dancoff Density Functional Approach to Potential Energy Surfaces for Photochemistry J. Phys. Chem. Lett. 2013, 4, 253-258
47. Warshel, A.; Levitt, M. Theoretical studies of enzymic reactions: Dielectric, electrostatic and steric stabilization of the carbonium ion in the reaction of lysozyme J. Mol. Biol. 1976, 103, 227-249
48. Dapprich, S. A new ONIOM implementation in Gaussian98. Part I. The calculation of energies, gradients, vibrational frequencies and electric field derivatives J. Mol. Struct. (THEOCHEM) 1999, 461-462, 1-21
49. Vreven, T.; Morokuma, K.; Farkas, Ö.; Schlegel, H. B.; Frisch, M. J. Geometry optimization with QM/MM, ONIOM, and other combined methods. I. Microiterations and constraints J. Comput. Chem. 2003, 24, 760-769
50. Vreven, T.; Byun, K. S.; Komáromi, I.; Dapprich, S.; Montgomery, J. A.; Morokuma, K.; Frisch, M. J. Combining Quantum Mechanics Methods with Molecular Mechanics Methods in ONIOM J. Chem. Theory Comput. 2006, 2, 815-826
51. Rappe, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A.; Skiff, W. M. UFF, a full periodic table force field for molecular mechanics and molecular dynamics simulations J. Am. Chem. Soc. 1992, 114, 10024-10035
52. Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Electronic structure calculations on workstation computers: The program system turbomole Chem. Phys. Lett. 1989, 162, 165-169
53. Frisch, M. J.; Gaussian 09, Revision A.02; Gaussian Inc.: Wallingford, CT, 2009.
54. Hanwell, M. D.; Curtis, D. E.; Lonie, D. C.; Vandermeersch, T.; Zurek, E.; Hutchison, G. R. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform J. Cheminf. 2012, 4, 17
55. Steffen, C.; Thomas, K.; Huniar, U.; Hellweg, A.; Rubner, O.; Schroer, A. TmoleX-A graphical user interface for TURBOMOLE J. Comput. Chem. 2010, 31, 2967-2970
56. POV-Ray 3.7; Persistence of Vision Raytracer Pty. Ltd., http://povray.org/.
57. Spartan 08; Wavefunction, Inc.: Irvine, CA, 2008.
58. Harbach, P. H. P.; Dreuw, A. In Modeling of Molecular Properties; Comba, P., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim and Germany, 2011; pp 29-47.
59. Martin, R. L. Natural transition orbitals J. Chem. Phys. 2003, 118, 4775
60. Plasser, F.; Lischka, H. Analysis of Excitonic and Charge Transfer Interactions from Quantum Chemical Calculations J. Chem. Theory Comput. 2012, 8, 2777-2789
61. Plötner, J.; Dreuw, A. Pigment Yellow 101: A showcase for photo-initiated processes in medium-sized molecules Chem. Phys. 2008, 347, 472-482
62. Plötner, J.; Tozer, D. J.; Dreuw, A. Dependence of Excited State Potential Energy Surfaces on the Spatial Overlap of the Kohn-Sham Orbitals and the Amount of Nonlocal Hartree-Fock Exchange in Time-Dependent Density Functional Theory J. Chem. Theory Comput. 2010, 6, 2315-2324
63. Mulliken, R. S. Electronic Population Analysis on LCAO[Single Bond]MO Molecular Wave Functions. I J. Chem. Phys. 1955, 23, 1833
64. Rappe, A. K.; Goddard, W. A. Charge equilibration for molecular dynamics simulations J. Phys. Chem. 1991, 95, 3358-3363