Photoisomerization dynamics and pathways of trans - And cis -azobenzene in solution from broadband femtosecond spectroscopies and calculations

Journal of Physical Chemistry B

Volumn 118, Issue 29, 2014, Pages 8756-8771

  Quick, M ^a   Dobryakov, A L ^a   Gerecke, M ^a   Richter, C ^a   Berndt, F ^a   Ioffe, I N ^b   Granovsky, A A ^c   Mahrwald, R ^a   Ernsting, N P ^a   Kovalenko, S A ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

^c Firefly Project   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ISOMERS; PHOTOISOMERIZATION; QUANTUM CHEMISTRY;

FEMTOSECOND SPECTROSCOPY; ISOMERIZATION KINETICS; ISOMERIZATION YIELDS; POPULATION RELAXATION; QUANTITATIVE COMPARISON; QUANTUM-CHEMICAL CALCULATION; STIMULATED RAMAN SPECTROSCOPY; TRANSIENT ABSORPTION;

AZOBENZENE;

EID: 84905042036     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp504999f     Document Type: Article

References (63)

1. Rau, H.; Lueddecke, E. On the Rotation-Inversion Controversy on Photoisomerization of Azobenzenes. Experimental Proof of Inversion J. Am. Chem. Soc. 1982, 104, 1616-1620
2. Rau, H.; Shen, Y.-Q. Photoisomerization of Sterically Hindered Azobenzenes J. Photochem. Photobiol., A 1988, 42, 321-327
3. Rau, H. Photoisomerization of Benzenes. In Photoreactive Organic Thin Films; Academic Press: Boston, 2002.
4. 1 (nπ) Absorption Bands J. Am. Chem. Soc. 2009, 131, 15594-15595
5. Waldeck, D. H. Photoisomerization Dynamics of Stilbenes Chem. Rev. 1991, 91, 415-436
6. Pollard, M. M.; Meetsma, A.; Feringa, B. L. A Redesign of Light-Driven Rotary Molecular Motors Org. Biomol. Chem. 2008, 6, 507-512
7. Liu, F.; Morokuma, K. Computational Study on the Working Mechanism of a Stilbene Light-Driven Molecular Rotary Motor: Sloped Minimal Energy Path and Unidirectional Nonadiabatic Photoisomerization J. Am. Chem. Soc. 2012, 134, 4864-4876
8. Khan, A.; Kaiser, C.; Hecht, S. Prototype of a Photoswitchable Foldamer Angew. Chem., Int. Ed. 2006, 45, 1878-1881
9. Bleger, D.; Liebig, T.; Thiermann, R.; Maskos, M.; Rabe, J. P.; Hecht, S. Light-Orchestrated Macromolecular "Accordions": Reversible Photoinduced Shrinking of Rigid-Rod Polymers Angew. Chem., Int. Ed. 2011, 50, 12559-12563
10. Yager, K. G.; C. Barrett, C. J. Novel Photo-Switching Using Azobenzene Functional Materials J. Photochem. Photobiol., A 2006, 182, 250-261
11. Böckmann, M.; Doltsinis, N. L.; Marx, D. Enhanced Photoswitching of Bridged Azobenzene Studied by Nonadiabatic ab Initio Simulation J. Chem. Phys. 2012, 137 (22A505) 1-10
12. Böckmann, M.; Doltsinis, N. L.; Marx, D. Nonadiabatic Hybrid Quantum and Molecular Mechanic Simulations of Azobenzene Photoswitching in Bulk Liquid Environment J. Phys. Chem. A 2010, 114, 745-754
13. Liu, R. S. H.; Asato, A. E. The Primary Process of Vision and the Structure of Bathorhodopsin: A Mechanism for Photoisomerization of Polyenes Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 259-263
14. Liu, R. S. H.; Hammond, G. S. The case of Medium-Dependent Dual Mechanisms for Photoisomerization: One-Bond Flip and Hula-Twist Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 11153-11158
15. Ruiz, D. S.; Cembran, A.; Garavelli, M.; Olivucci, M.; Fuß, W. Structure of the Conical Intersections Driving the cis-trans Photoizomerization of Conjugated Molecules Photochem. Photbiol. 2002, 76, 622-633
16. Yuan, S.; Dou, Y.; Wu, W.; Hu, Y.; Zhao, J. Why Does trans-Azobenzene Have a Smaller Isomerization Yield for ππ* Excitation than for nπ* Excitation J. Phys. Chem. A 2008, 112, 13326-13334
17. Jiang, C.-W.; Xie, R.-H.; Li, F.-L.; Allen, R. E. Comparative Studies of the trans-cis Photoisomerizations of Azobenzene and a Bridged Azobenzene J. Phys. Chem. A 2011, 115, 244-249
18. Bortolus, P.; Monti, S. Cis-Trans Photoisomerization of Azobenzene. Solvent and Triplet Donors Effects J. Phys. Chem. 1979, 83, 648-652
19. Siampiringue, N.; Guyot, G.; Monti, S.; Bortolus, P. The Cis-Trans Photoisomerization of Azobenzene: An Experimental Reexamination J. Photochem. 1987, 37, 185-188
20. Lednev, I. K.; Ye, T.-Q.; Hester, R. E.; Moore, J. N. Femtosecond Time-Resolved UV-Visible Absorption Spectroscopy of Trans-Azobenzene in Solution J. Phys. Chem. 1996, 100, 13338-13341
21. Lednev, I. K.; Ye, T.-Q.; Matousek, P.; Towrie, M.; Foggi, P.; Neuwahl, F. V. R.; Umapathy, S.; Hester, R. E.; Moore, J. N. Femtosecond Time-Resolved UV-Visible Absorption Spectroscopy of Trans-Azobenzene: Dependence on Excitation Wavelength Chem. Phys. Lett. 1998, 290, 68-74
22. Lednev, I. K.; Ye, T.-Q.; Abbott, L. C.; Hester, R. E.; Moore, J. N. Photoisomerization of a Capped Azobenzene in Solution Probed by Ultrafast Time-Resolved Electronic Absorption Spectroscopy J. Phys. Chem. A 1998, 102, 9161-9166
23. Nägele, T.; Hoche, R.; Zinth, W.; Wachtveitl, J. Femtosecond Photoisomerization of Cis-Azobenzene Chem. Phys. Lett. 1997, 272, 489-495
24. Satzger, H.; Spörlein, S.; Root, C.; Wachtveitl, J.; Zinth, W.; Gilch, P. Fluorescence Spectra of Trans- and Cis-Azobenzene-Emission from the Frank-Condon State Chem. Phys. Lett. 2003, 372, 216-223
25. Satzger, H.; Root, C.; Braun, M. Excited-State Dynamics of Trans- and Cis-Azobenzene after UV Excitation in the ππ* Band J. Phys. Chem. A 2004, 108, 6265-6271
26. 2 State of a Liquid Crystalline Trans-Azobenzene Chem. Phys. Lett. 1998, 288, 77-82
27. Fujino, T.; Tahara, T. Picosecond Time-Resolved Raman Study of trans-Azobenzene J. Phys. Chem. A 2000, 104, 4203-4210
28. Fujino, T.; Arzhantsev S, Yu.; Tahara, T. Femtosecond Time-Resolved Fluorescence Study of Photoisomerization of Trans-Azobenzene J. Phys. Chem. A 2001, 105, 8123-8129
29. Schultz, T.; Quenneville, J.; Levine, B.; Toniolo, A.; Martinez, T. J.; Lochbrunner, S.; Schmitt, M.; Shaffer, J. P.; Zgierski, M. Z.; Stolow, A. Mechanism and Dynamics of Azobenzene Photoisomerization J. Am. Chem. Soc. 2003, 125, 8098-8099
30. 1 State Phys. Chem. Chem. Phys. 2005, 7, 1985-1989
31. 1 Excitation: A Femtosecond Fluorescence Anisotropy Study J. Am. Chem. Soc. 2004, 126, 10109-10118
32. Bandara, H. M. D.; Burdette, S. C. Photoisomerization in Different Classes of Azobenzene Chem. Soc. Rev. 2012, 41, 1809-1825
33. Fliegl, H.; Köhn, A.; Hättig, C.; Ahlrichs, R. Ab Initio Calculation of the Vibrational and Electronic Spectra of trans- and cis-Azobenzene J. Am. Chem. Soc. 2003, 125, 9821-9827
34. 1 Surface J. Phys. Chem. A 2004, 108, 950-956
35. Crecca, C. R.; Roitberg, A. E. Theoretical Study of the Isomerization Mechanism of Azobenzene and Disubstituted Azobenzene Derivatives J. Phys. Chem. A 2006, 110, 8188-8203
36. Granucci, G.; Persico, M. Excited State Dynamics with the Direct Trajectory Surface Hopping Method: Azobenzene and its Derivatives as a case Study Theor. Chem. Acc. 2007, 117, 1131-1143
37. Cembran, A.; Bernardi, F.; Garavelli, M.; Gagliardi, L.; Orlandi, G. On the Mechanism of the cis-trans Isomerization in the Lowest Electronic States of Azobenzene: S0, S1, and T1 J. Am. Chem. Soc. 2004, 126, 3234-3243
38. Conti, I.; Garavelli, M.; Orlandi, G. The Different Photoisomerization Efficiency of Azobenzene in the Lowest nπ* and ππ* Singlets: The Role of a Phantom State J. Am. Chem. Soc. 2008, 130, 5216-5230
39. Nonnenberg, C.; Gaub, H.; Frank, I. First-principles Simulation of the Photoreaction of a Capped Azobenzene: the Rotational Pathway is Feasible ChemPhysChem 2006, 7, 1455-1461
40. Harabuchi, Y.; Ishii, M.; Nakayama, F.; Noro, T.; Taketsugu, T. A multireference Perturbation Study of the NN Stretching Frequency of trans-Azobenzene in nπ* Excitation and an Implication for the Photoisomerization Mechanism J. Chem. Phys. 2013, 138, 064305
41. Kovalenko, S. A.; Dobryakov, A. L.; Ruthmann, J.; Ernsting, N. P. Femtosecond Spectroscopy of Condensed Phases with Chirped Supercontinuum Probing Phys. Rev. A 1999, 59, 2369-2384
42. Dobryakov, A. L.; Kovalenko, S. A.; Weigel, A.; Perez-Lustres, J. L.; Lange, J.; Müller, A.; Ernsting, N. P. Rev. Sci. Instrum. 2010, 81, 113106
43. Kovalenko, S. A.; Schanz, R.; Hennig, H.; Ernsting, N. P. Cooling Dynamics of an Optically Excited Molecular Probe in Solution from Femtosecond Broadband Transient Absorption Spectroscopy J. Chem. Phys. 2001, 115, 3256-3273
44. Perez-Lustres, J. L.; Rodriguez-Prieto, F.; Mosquera, M.; Senyushkina, T. A.; Ernsting, N. P.; Kovalenko, S. A. Ultrafast Proton Transfer to Solvent: Molecularity and Intermediates from Solvation- and Diffusion-Controlled Regimes J. Am. Chem. Soc. 2007, 129, 5408-5418
45. Karunakaran, V.; Kleinermanns, K.; Improta, R.; Kovalenko, S. A. Photoinduced Dynamics of Guanosine Monophosphate in Water from Broad-Band Transient Absorption Spectroscopy and Quantum-Chemical Calculations J. Am. Chem. Soc. 2009, 131, 5839-5850
46. Kovalenko, S. A.; Dobryakov, A. L.; Ioffe, I.; Ernsting, N. P. Evidence fort the Phantom State in photoinduced cis-trans Isomerization of Stilbene Chem. Phys. Lett. 2010, 493, 255-258
47. Berndt, F.; Dobryakov, A. L.; Quick, M.; Mahrwald, R.; Ernsting, N. P.; Lenoir, D.; Kovalenko, S. A. Long-Lived Perpendicular Conformation in the Photoisomerization Path of 1,1′-Dimethyl-stilbene and 1,1′- Diethylstilbene Chem. Phys. Lett. 2012, 544, 39-42
48. Quick, M.; Berndt, F.; Dobryakov, A. L.; Ioffe, I. N.; Granovsky, A. A.; Knie, C.; Mahrwald, R.; Lenoir, D.; Ernsting, N. P.; Kovalenko, S. A. Photoisomerization Dynamics of Stiff-Stilbene in Solution J. Phys. Chem. B 2014, 118, 1389-1402
49. Schanz, R.; Kovalenko, S. A.; Kharlanov, V.; Ernsting, N. P. Broad-Band Fluorescence Upconversion for Femtosecond Spectroscopy Appl. Phys. Lett. 2001, 79, 566-568
50. Kovalenko, S. A.; Schanz, R.; Senyushkina, T. A.; Ernsting, N. P. Femtosecond Spectroscopy of p -Dimethylaminocyanostilbene in Solution-no evidence for dual fluorescence Phys. Chem. Chem. Phys. 2002, 4, 703-707
51. Zhao, L.; Lustres, J. L. P.; Farztdinov, V.; Ernsting, N. P. Femtosecond Fluorescence Spectroscopy by Upconversion with Tilted Gate Pulses Phys. Chem. Chem. Phys. 2005, 7, 1716-1725
52. Sajadi, M.; Quick, M.; Ernsting, N. P. Femtosecond Broadband Fluorescence Spectroscopy by Down- and Up-Conversion in BBO Crystals Appl. Phys. Lett. 2013, 103, 173514
53. Zhang, X.-X.; Würth, C.; Zhao, L.; Resch-Genger, U.; Ernsting, N. P.; Sajadi, M. Femtosecond Broadband Fluorescence Upconversion Spectroscopy: Improved Setup and Photometric Correction Rev. Sci. Instrum. 2011, 82 (063108) 1-8
54. Kovalenko, S. A.; Dobrykov, A. L.; Ernsting, N. P. An Efficient Setup for Femtosecond Stimulated Raman Spectroscopy Rev. Sci. Instrum. 2011, 82 (063102) 1-10
55. Dobryakov, A. L.; Ioffe, I.; Granovsky, A. A.; Ernsting, N. P.; Kovalenko, S. A. Femtosecond Raman Spectra of cis-Stilbene and trans-Stilbene with Isotopomers in Solution J. Chem. Phys. 2012, 137 (244505) 1-16
56. 1 Raman Spectra of trans-Azobenzerne J. Chem. Phys. 2014, 140 (184310) 1-5
57. Granovsky, A. A. Extended Multi-Configuration Quasi-Degenerate Perturbation Theory: The New Approach to Multi-State Multi-Reference Perturbation Theory J. Chem. Phys. 2011, 134, 214113
58. Granovsky, A. A. Firefly, version 8.1.0. http://classic.chem.msu.su/gran/ firefly/index.html.
59. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
60. Laikov, D. N. Fast Evaluation of Density Functional Exchange-Correlation Terms Using the Expansion of the Electron Density in Auxiliary Basis Sets Chem. Phys. Lett. 1997, 281, 151-156
61. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
62. Ioffe, I. N.; Granovsky, A. A. Photoisomerization of Stilbene: The Detailed XMCQDPT2 Treatment J. Chem. Theory Comput. 2013, 9, 4973-4990
63. Sadovnichy, V.; Tikhonravov, A.; Voevodin, V.; Opanasenko, A. In Contemporary High Performance Computing; CRC Press: Boca Raton, FL, 2013; pp 283-307.