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Abstract:

Gas phase photodissociation electronic spectra of protonated azobenzene (ABH+) and 4-(dimethylamino)azobenzene (dmaABH+) were measured in a cryogenically cooled ion trap at temperatures of a few tens of Kelvin. Experimental results were complemented with electronic structure calculations in the ground state at the MP2/cc-pVDZ level of theory, and in the low lying excited states using the RI-CC2 method. Calculated energies revealed that only the trans isomers of the azonium molecular ions (protonation site on the azo group) will likely exist in the trap at the temperatures achieved in the experiment. The first transition of trans-ABH+ is π∗ ← π, and the absorption band in the spectrum appears strongly red-shifted from that of the neutral molecule. The calculations showed that upon excitation the quasi-planar ground state (S0) transforms into a chairlike excited state (S1) by twisting the CNNC dihedral angle about 96°. A 41 cm-1 active vibrational progression found in the ABH+ spectrum may be associated with the twisting of the azo bond. Conversely, the electronic spectrum of dmaABH+ exhibits a steep and unstructured S1 ← S0 absorption corresponding to a less distorted S1 state. The next two quasi-degenerate bands in the ABH+ spectrum evidence sharper onsets and a charge transfer character. Using a second fragmentation laser and an additional He cooling pulse in the trap, it was possible to measure the UV spectrum of cold benzenediazonium fragments. © 2016 American Chemical Society.

Registro:

Documento: Artículo
Título:Photodissociation UV-Vis spectra of cold protonated azobenzene and 4-(dimethylamino)azobenzene and their benzenediazonium cation fragment
Autor:Féraud, G.; Dedonder-Lardeux, C.; Jouvet, C.; Marceca, E.
Filiación:CNRS, Aix-Marseille Université, PIIM UMR 7365, Avenue Escadrille Normandie-Niémen, Marseille Cedex 20, 13397, France
INQUIMAE, FCEN-UBA, Ciudad Universitaria, 3er piso, Pabellón II, Buenos Aires, C1428EGA, Argentina
LERMA, Sorbonne Universités, UPMC Univ. Paris 06, Observatoire de Paris, PSL Research University, CNRS, Paris, F-75252, France
Palabras clave:Absorption spectroscopy; Azobenzene; Charge transfer; Chemical reactions; Dihedral angle; Electronic structure; Ground state; Isomers; Photodissociation; Protonation; Ultraviolet spectroscopy; Electronic spectrum; Electronic structure calculations; Low-lying excited state; Molecular ions; Neutral molecules; Protonation site; UV-vis spectra; Vibrational progressions; Excited states
Año:2016
Volumen:120
Número:22
Página de inicio:3897
Página de fin:3905
DOI: http://dx.doi.org/10.1021/acs.jpca.6b03505
Título revista:Journal of Physical Chemistry A
Título revista abreviado:J Phys Chem A
ISSN:10895639
CODEN:JPCAF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10895639_v120_n22_p3897_Feraud

Referencias:

  • Schulze, F.W., Petrick, H.J., Cammenga, H.K., Klinge, H., Thermodynamic Properties of the Structural Analogues Benzo[c]cinnoline, trans-Azobenzene, and cis-Azobenzene (1977) Z. Phys. Chem., 107, pp. 1-19
  • Andersson, J.A., Petterson, R., Tegnér, L., Flash Photolysis Experiments in the Vapour Phase at Elevated Temperatures I: Spectra of Azobenzene and the Kinetics of its Thermal cis-trans Isomerization (1982) J. Photochem., 20, pp. 17-32
  • Ikeda, T., Tsutsumi, O., Optical Switching and Image Storage by Means of Azobenzene Liquid-Crystal Films (1995) Science, 268, pp. 1873-1875
  • Tamai, N., Miyasaka, H., Ultrafast Dynamics of Photochromic Systems (2000) Chem. Rev., 100, pp. 1875-1890
  • Kobayashi, T., Degenkolb, E.O., Rentzepis, P.M., Picosecond Spectroscopy of 1-phenylazo-2-hydroxynaphthalene (1979) J. Phys. Chem., 83, pp. 2431-2434
  • Rau, H., Lueddecke, E., On the Rotation-Inversion Controversy on Photoisomerization of Azobenzenes. Experimental Proof of Inversion (1982) J. Am. Chem. Soc., 104, pp. 1616-1620
  • Fujino, T., Tahara, T., Picosecond Time-Resolved Raman Study of trans-Azobenzene (2000) J. Phys. Chem. A, 104, pp. 4203-4210
  • Chang, C.-W., Lu, Y.-C., Wang, T.-T., Diau, E.W.-G., Photoisomerization Dynamics of Azobenzene in Solution with S1 Excitation: A Femtosecond Fluorescence Anisotropy Study (2004) J. Am. Chem. Soc., 126, pp. 10109-10118
  • Tan, E.M.M., Amirjalayer, S., Smolarek, S., Vdovin, A., Zerbetto, F., Buma, W.J., Fast Photodynamics of Azobenzene Probed by Scanning Excited-State Potential Energy Surfaces Using Slow Spectroscopy (2015) Nat. Commun., 6, p. 5860
  • Monti, S., Orlandi, G., Palmieri, P., Features of the Photochemically Active State Surfaces of Azobenzene (1982) Chem. Phys., 71, pp. 87-99
  • Crecca, C.R., Roitberg, A.E., Theoretical Study of the Isomerization Mechanism of Azobenzene and Disubstituted Azobenzene Derivatives (2006) J. Phys. Chem. A, 110, pp. 8188-8203
  • 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 (2008) J. Am. Chem. Soc., 130, pp. 5216-5230
  • Cusati, T., Granucci, G., Persico, M., Photodynamics and Time-Resolved Fluorescence of Azobenzene in Solution: A Mixed Quantum-Classical Simulation (2011) J. Am. Chem. Soc., 133, pp. 5109-5123
  • Bandara, H.M.D., Burdette, S.C., Photoisomerization in Different Classes of Azobenzene (2012) Chem. Soc. Rev., 41, pp. 1809-1825
  • Mahimwalla, Z., Yager, K.G., Mamiya, J., Shishido, A., Priimagi, A., Barrett, C.J., Azobenzene Photomechanics: Prospects and Potential Applications (2012) Polym. Bull., 69, pp. 967-1006
  • Beharry, A.A., Woolley, G.A., Azobenzene Photoswitches for Biomolecules (2011) Chem. Soc. Rev., 40, pp. 4422-4437
  • Shishido, A., Rewritable Holograms Based on Azobenzene-Containing Liquid-Crystalline Polymers (2010) Polym. J., 42, pp. 525-533
  • Jaffé, H.H., Yeh, S.-J., Gardner, R.W., The Electronic Spectra of Azobenzene Derivatives and Their Conjugate Acids (1958) J. Mol. Spectrosc., 2, pp. 120-136
  • Matazo, D.R.C., Ando, R.A., Borin, A.C., Santos, P.S., Azo-Hydrazone Tautomerism in Protonated Aminoazobenzenes: Resonance Raman Spectroscopy and Quantum-Chemical Calculations (2008) J. Phys. Chem. A, 112, pp. 4437-4443
  • Dunn, N.J., Humphries, W.H., Offenbacher, A.R., King, T.L., Gray, J.A., PH-Dependent cis→trans Isomerization Rates for Azobenzene Dyes in Aqueous Solution (2009) J. Phys. Chem. A, 113, pp. 13144-13151
  • Sokalski, W.A., Góra, R.W., Bartkowiak, W., Kobylinski, P., Sworakowski, J., Chyla, A., Leszczynski, J., New Theoretical Insight into the Thermal cis-trans Isomerization of Azo Compounds: Protonation Lowers the Activation Barrier (2001) J. Chem. Phys., 114, pp. 5504-5508
  • Féraud, G., Esteves-López, N., Dedonder-Lardeux, C., Jouvet, C., UV Spectroscopy of Cold Ions as a Probe of the Protonation Site (2015) Phys. Chem. Chem. Phys., 17, pp. 25755-25760
  • Alata, I., Bert, J., Broquier, M., Dedonder-Lardeux, C., Féraud, G., Grégoire, G., Soorkia, S., Jouvet, C., Electronic Spectra of the Protonated Indole Chromophore in the Gas Phase (2013) J. Phys. Chem. A, 117, pp. 4420-4427
  • Féraud, G., Dedonder-Lardeux, C., Jouvet, C., Inokuchi, Y., Haino, T., Sekiya, R., Ebata, T., Development of Ultraviolet-Ultraviolet Hole-Burning Spectroscopy for Cold Gas-Phase Ions (2014) J. Phys. Chem. Lett., 5, pp. 1236-1240
  • Kang, H., Féraud, G., Dedonder-Lardeux, C., Jouvet, C., New Method for Double-Resonance Spectroscopy in a Cold Quadrupole Ion Trap and Its Application to UV-UV Hole-Burning Spectroscopy of Protonated Adenine Dimer (2014) J. Phys. Chem. Lett., 5, pp. 2760-2764
  • Ahlrichs, R., Bär, M., Häser, M., Horn, H., Kölmel, C., Electronic Structure Calculations on Workstation Computers: The Program System Turbomole (1989) Chem. Phys. Lett., 162, pp. 165-169
  • Hättig, C., Weigend, F., CC2 Excitation Energy Calculations on Large Molecules Using the Resolution of the Identity Approximation (2000) J. Chem. Phys., 113, pp. 5154-5161
  • Dreuw, A., Head-Gordon, M., Failure of Time-Dependent Density Functional Theory for Long-Range Charge-Transfer Excited States: The Zincbacteriochlorin-Bacteriochlorin and Bacteriochlorophyll-Spheroidene Complexes (2004) J. Am. Chem. Soc., 126, pp. 4007-4016
  • Féraud, G., Broquier, M., Dedonder-Lardeux, C., Grégoire, G., Soorkia, S., Jouvet, C., Photofragmentation Spectroscopy of Cold Protonated Aromatic Amines in the Gas Phase (2014) Phys. Chem. Chem. Phys., 16, pp. 5250-5259
  • Féraud, G., Dedonder-Lardeux, C., Soorkia, S., Jouvet, Photo-Fragmentation Spectroscopy of Benzylium and 1-Phenylethyl Cations. C (2014) J. Chem. Phys., 140, p. 024302
  • Horai, H., Arita, M., Kanaya, S., Nihei, Y., Ikeda, T., Suwa, K., Ojima, Y., Aoshima, K., MassBank: A Public Repository for Sharing Mass Spectral Data for Life Sciences (2010) J. Mass Spectrom., 45, pp. 703-714
  • Berdakin, M., Féraud, G., Dedonder-Lardeux, C., Jouvet, C., Pino, G.A., Excited States of Protonated DNA/RNA Bases (2014) Phys. Chem. Chem. Phys., 16, pp. 10643-10650
  • Gasper, S.M., Devadoss, C., Schuster, G.B., Photolysis of Substituted Benzenediazonium Salts: Spin-Selective Reactivity of Aryl Cations (1995) J. Am. Chem. Soc., 117, pp. 5206-5211
  • Sukigara, M., Kikuchi, S., Studies of the Photochemistry of Aromatic Diazo Compounds. I. Electronic Structure and Photodecomposition of Benzenediazonium Salt (1967) Bull. Chem. Soc. Jpn., 40, pp. 461-466
  • Kuroda, Y., Lee, H., Kuwae, A., Direct Evidence for the Site of Protonation of 4-Aminoazobenzene by Nitrogen-15 and Carbon-13 Nuclear Magnetic Resonance Spectroscopy (1980) J. Phys. Chem., 84, pp. 3417-3423
  • Liwo, A., Tempczyk, A., Widernik, T., Klentak, T., Czermiński, J., A Theoretical Study of Protonation and Tautomerization of N-Substituted Aminoazobenzenes (1994) J. Chem. Soc., Perkin Trans. 2, pp. 71-75
  • Féraud, G., Broquier, M., Dedonder-Lardeux, C., Grégoire, G., Soorkia, S., Jouvet, C., Photofragmentation Spectroscopy of Cold Protonated Aromatic Amines in the Gas Phase (2014) Phys. Chem. Chem. Phys., 16, pp. 5250-5259
  • Noble, J.A., Dedonder, C., Jouvet, C., The Electronic Spectra of Protonated Nitrogen-Substituted Polycyclic Aromatic Hydrocarbon Molecules (2015) Astron. Astrophys., 577, p. A79
  • Dedonder, C., Féraud, G., Jouvet, C., Communication: Identification of Daughter Ions through Their Electronic Spectroscopy at Low Temperature (2014) J. Chem. Phys., 141, p. 131101

Citas:

---------- APA ----------
Féraud, G., Dedonder-Lardeux, C., Jouvet, C. & Marceca, E. (2016) . Photodissociation UV-Vis spectra of cold protonated azobenzene and 4-(dimethylamino)azobenzene and their benzenediazonium cation fragment. Journal of Physical Chemistry A, 120(22), 3897-3905.
http://dx.doi.org/10.1021/acs.jpca.6b03505
---------- CHICAGO ----------
Féraud, G., Dedonder-Lardeux, C., Jouvet, C., Marceca, E. "Photodissociation UV-Vis spectra of cold protonated azobenzene and 4-(dimethylamino)azobenzene and their benzenediazonium cation fragment" . Journal of Physical Chemistry A 120, no. 22 (2016) : 3897-3905.
http://dx.doi.org/10.1021/acs.jpca.6b03505
---------- MLA ----------
Féraud, G., Dedonder-Lardeux, C., Jouvet, C., Marceca, E. "Photodissociation UV-Vis spectra of cold protonated azobenzene and 4-(dimethylamino)azobenzene and their benzenediazonium cation fragment" . Journal of Physical Chemistry A, vol. 120, no. 22, 2016, pp. 3897-3905.
http://dx.doi.org/10.1021/acs.jpca.6b03505
---------- VANCOUVER ----------
Féraud, G., Dedonder-Lardeux, C., Jouvet, C., Marceca, E. Photodissociation UV-Vis spectra of cold protonated azobenzene and 4-(dimethylamino)azobenzene and their benzenediazonium cation fragment. J Phys Chem A. 2016;120(22):3897-3905.
http://dx.doi.org/10.1021/acs.jpca.6b03505