Skip to main content
SpringerLink
Log in

Temperature influence on deactivation paths and tautomeric equilibrium of some photochromic Schiff bases studied by time-resolved and stationary spectroscopy

  • Paper
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

The effect of temperature on spectroscopic properties (stationary and time-resolved) of selected compounds belonging to the salicylideneaniline and hydroquinone families of photochromic Schiff bases is studied. The nonradiative decay of the excited keto tautomer consists of two components: the temperature-independent one (internal conversion, dominant below 200 K) and the temperature-dependent one (assigned to structural changes). The parameters of these components are remarkably different in the two families of the photochromic compounds. The influence of the hydrogen bonding ability of the solvent on the tautomeric equilibrium between the enol and keto forms indicates changes in the order of the ground state energy levels when going from methanol to trifluoroethanol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. E. Hadjoudis, I. M. Mavridis, Photochromism and thermochromism of Schiff bases in the solid state: Structural aspects, Chem. Soc. Rev., 2004, 33, 579.

    CAS  PubMed  Google Scholar 

  2. M. Sliwa, S. Letard, I. Malfant, M. Nierlich, P. G. Lacroix, T. Asahi, H. Masuhara, P. Yu, K. Nakatani, Design, Synthesis, Structural and Nonlinear Optical Properties of Photochromic Crystals: Toward Reversible Molecular Switches, Chem. Mater., 2005, 17, 4727–4735.

    Article  CAS  Google Scholar 

  3. M. Irie, special issue on Photochromism: Memories and Switches, Chem. Rev., 2000, 100, 1683.

    CAS  PubMed  Google Scholar 

  4. R. V. Andes, D. M. Manikowski, Photochromism of salicylidene aniline, Appl. Opt., 1968, 7, 1179.

    Article  CAS  PubMed  Google Scholar 

  5. M. Ziółek, J. Kubicki, A. Maciejewski, R. Naskręcki, A. Grabowska, An ultrafast excited state intramolecular proton transfer (ESPIT) and photochromism of salicylideneaniline (SA) and its “double” analogue salicylaldehyde azine (SAA). A controversial case, Phys. Chem. Chem. Phys., 2004, 6, 4682–4689.

    Article  Google Scholar 

  6. W. Rodríguez-Córdoba, J. S. Zugazagoitia, E. Collado-Fregoso, J. Peon, Excited State Intramolecular Proton Transfer in Schiff Bases. Decay of the Locally Excited Enol State Observed by Femtosecond Resolved Fluorescence, J. Phys. Chem. A, 2007, 111, 6241–6247.

    Article  PubMed  Google Scholar 

  7. J. M. Ortiz-Sánchez, R. Gelabert, M. Moreno, J. M. Lluch, Electronic-structure and quantum dynamical study of the photochromism of the aromatic Schiff base salicylideneaniline, J. Chem. Phys., 2008, 129, 214308.

    Article  PubMed  Google Scholar 

  8. N. P. Ernsting, S. A. Kovalenko, T. Senyushkina, J. Saam, V. Farztdinov, Wave-Packet-Assisted Decomposition of Femtosecond Transient UV/vis Absorption Spectra: Application to Excited-State Intramolecular Proton Transfer in Solution, J. Phys. Chem. A, 2001, 105, 3443–3453.

    Article  CAS  Google Scholar 

  9. M. Rini, A. Kummrow, J. Dreyer, E. T. J. Nibbering, T. Elsaesser, Femtosecond mid-infrared spectroscopy of condensed phase hydrogen-bonded systems as a probe of structural dynamics, Faraday Discuss., 2003, 122, 27–40.

    Article  CAS  PubMed  Google Scholar 

  10. S. Lochbrunner, A. J. Wurzer, E. Riedle, Microscopic mechanism of ultrafast excited-state intramolecular proton transfer: A 30-fs study of 2-(2′-hydroxyphenyl)benzothiazole, J. Phys. Chem. A, 2003, 107, 10580–10590.

    Article  CAS  Google Scholar 

  11. R. de Vivie-Riedle, V. de Waele, L. Kurtz, E. Riedle, Ultrafast excited-state proton transfer of 2-(2′-hydroxyphenyl)benzothiazole: Theoretical analysis of the skeletal deformations and the active vibrational modes, J. Phys. Chem. A, 2003, 107, 10591–10599.

    Article  Google Scholar 

  12. K. Kownacki, A. Mordzinski, R. Wilbrandt, A. Grabowska, Laser-induced absorption and fluorescence studies of photochromic Schiff bases, Chem. Phys. Lett., 1994, 227, 270–276.

    Article  CAS  Google Scholar 

  13. T. Rosenfeld, M. Ottolenghi, A. Y. Meyer, Photochromic Anils. Structure of Photoisomers and Thermal Relaxation Processes, Mol. Photochem., 1973, 5, 39–60.

    CAS  Google Scholar 

  14. M. I. Knyazhansky, A. V. Metelitsa, M. E. Kletskii, A. A. Millov, S. O. Besugliy, The structural transformations and photo-induced processes in salicylidene alkylimines, J. Mol. Struct., 2000, 526, 65.

    Article  CAS  Google Scholar 

  15. R. S. Becker, C. Lenoble, A. Zein, A comprehensive investigation of the photophysics and photochemistry of salicylideneaniline and derivatives of phenylbenzothiazole including solvent effects, J. Phys. Chem., 1987, 91, 3509–3517.

    Article  CAS  Google Scholar 

  16. C. Okabe, T. Nakabayashi, Y. Inokuchi, N. Nishi, H. Sekiya, Ultrafast excited-state dynamics in photochromic N-salicylideneaniline studied by femtosecond time-resolved REMPI spectroscopy, J. Chem. Phys., 2004, 121, 9436–9442.

    Article  CAS  PubMed  Google Scholar 

  17. M. Ziółek, G. Burdziński, K. Filipczak, J. Karolczak, A. Maciejewski, Spectroscopic and photophysical studies of the hydroquinone family of photochromic Schiff bases analyzed over a 17-orders-of-magnitude time scale, Phys. Chem. Chem. Phys., 2008, 10, 1304–1318.

    Article  PubMed  Google Scholar 

  18. M. Ziolek, G. Burdzinski, J. Karolczak, Influence of Intermolecular Hydrogen Bonding on the Photochromic Cycle of the Aromatic Schiff Base N,N′-Bis(salicylidene)-p-phenylenediamine in Solution, J. Phys. Chem. A, 2009, 113, 2854–2864.

    Article  CAS  PubMed  Google Scholar 

  19. M. Ziółek, J. Kubicki, A. Maciejewski, R. Naskręcki, A. Grabowska, Enol-keto tautomerism of aromatic photochromic Schiff base N,N′-bis(salicylidene)-p-phenylenediamine: Ground state equilibrium and excited state deactivation studied by solvatochromic measurements on ultrafast time scale, J. Chem. Phys., 2006, 124, 124518.

    PubMed  Google Scholar 

  20. T. Wróżowa, B. Ciesielska, D. Komar, J. Karolczak, A. Maciejewski, J. Kubicki, Measurements of picosecond lifetimes by time correlated single photon counting method: The effect of the refraction index of the solvent on the instrument response function, Rev. Sci. Instrum., 2004, 75, 3107–3121.

    Article  Google Scholar 

  21. A. A. Granovsky, PC GAMESS/Firefly version 7.1.C, http://classic.chem.msu.su/gran/gamess/index.html, 2008.

    Google Scholar 

  22. R. W. Taft, M. J. Kamlet, The solvatochromic comparison method. 2. The alpha-scale of solvent hydrogen-bond donor (HBD) acidities, J. Am. Chem. Soc., 1976, 98, 2886–2894.

    Article  CAS  Google Scholar 

  23. V. Vargas, L. Amigo, A study of the tautomers of N-salicylidene-p-X-aniline compounds in methanol, J. Chem. Soc., Perkin Trans. 2, 2001, 1124–1129.

    Google Scholar 

  24. W. A. F. Fabian, L. Antonov, D. Nedeltcheva, F. S. Kamounah, P. J. Taylor, Tautomerism in hydroxynaphthaldehyde anils and azo analogues: a combined experimental and computational study, J. Phys. Chem. A, 2004, 108, 7603–7612.

    Article  CAS  Google Scholar 

  25. T. Dziembowska, E. Jagodzinska, Z. Rozwadowski, M. Kotfica, Solvent effect on intramolecular proton transfer equilibrium in some N-(R-salicylidene)-alkylamines, J. Mol. Struct., 2001, 598, 229–234.

    Article  CAS  Google Scholar 

  26. L. Antonov, W. M. F. Fabian, D. Nedeltcheva, F. S. Kamounah, Tautomerism of 2-hydroxynaphthaldehyde Schiff bases, J. Chem. Soc., Perkin Trans. 2, 2000, 1173–1179.

    Google Scholar 

  27. T. Fujiwara, J. Harada, K. Ogawa, Hydrogen-Bonded Cyclic Dimer Formation in Temperature-Induced Reversal of Tautomerism of Salicylideneanilines, J. Phys. Chem. A, 2009, 113, 1822–1826.

    Article  CAS  PubMed  Google Scholar 

  28. K. Dobek, Temperature influence on the energy of nonspecific and specific interactions taking place between 4-aminophthalimide (4-AP) and homogeneous solvents, Photochem. Photobiol. Sci., 2008, 7, 361–370.

    Article  CAS  PubMed  Google Scholar 

  29. J. S. Stephan, C. Ríos Rodríguez, K. H. Grellmann, K. A. Zachariasse, Flash-photolysis of 2-(2′-hydroxyphenyl)-3-H-indole. Ground state keto–enol tautomerization by mutual hydrogen exchange and by proton catalysis, Chem. Phys., 1994, 186, 435–446.

    Article  CAS  Google Scholar 

  30. M. Guillaume, B. Champagne, N. Markova, V. Enchev, F. Castet, Ab Initio Investigation on the Second-Order Nonlinear Optical Responses in Keto-Enol Equilibria of Salicylideneanilines, J. Phys. Chem. A, 2007, 111, 9914–9923.

    Article  CAS  PubMed  Google Scholar 

  31. A. Plaquet, M. Guillaume, B. Champagne, L. Rougier, F. Mancüois, V. Rodriguez, J.-L. Pozzo, L. Ducasse, F. Castet, Investigation on the Second-Order Nonlinear Optical Responses in the Keto-Enol Equilibrium of Anil Derivatives, J. Phys. Chem. C, 2008, 112, 5638–5645.

    Article  CAS  Google Scholar 

  32. K. Kownacki, Ł. Kaczmarek, A. Grabowska, Single versus double proton transfer in the photochromic Schiff bases. Electronic spectroscopy and synthesis of model compounds, Chem. Phys. Lett., 1993, 210, 373–379.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Photochemistry Laboratory, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780, Poznan, Poland

    Katarzyna Filipczak

  2. Quantum Electronics Laboratory, Faculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614, Poznan, Poland

    Jerzy Karolczak & Marcin Ziółek

  3. Center for Ultrafast Laser Spectroscopy, Adam Mickiewicz University, Umultowska 85, 61-614, Poznan, Poland

    Jerzy Karolczak

Authors
  1. Katarzyna Filipczak
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jerzy Karolczak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Marcin Ziółek
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Marcin Ziółek.

Additional information

† Electronic supplementary information (ESI) available: Fig. S1–S7 and Tables S1 and S2. See DOI: 10.1039/b9pp00040b

Rights and permissions

Reprints and permissions

About this article

Cite this article

Filipczak, K., Karolczak, J. & Ziółek, M. Temperature influence on deactivation paths and tautomeric equilibrium of some photochromic Schiff bases studied by time-resolved and stationary spectroscopy. Photochem Photobiol Sci 8, 1603–1610 (2009). https://doi.org/10.1039/b9pp00040b

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/b9pp00040b

Search

Navigation