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Photoinduced reversible changes in the electronic structure of photochromic diarylethene films

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Abstract

The change in the valence electronic structure upon switching of two photochromic diarylethene derivatives, i.e. 1,2-bis(2-methyl-5-p-tolylthiophen-3-yl)cyclopent-1-ene (DAE1) and 1,2-bis(5-(4-hexyloxycarbonylphenyl)-2-methylthiophen-3-yl)cyclopent-1-ene (DAE2), was measured by photoelectron spectroscopy. Switching between open and closed forms was followed in situ upon illumination. The increase of the ionization energy from the closed to the open form was 0.85 eV for DAE1 and 0.80 eV for DAE2. For DAE1, the work function also decreased by 0.25 eV upon switching, which is explained by a decrease of the intrinsic molecular dipole moment and a preferential orientation of molecules in thin films.

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References

  1. T. Tsujioka, M. Irie, J. Photochem. Photobiol., C, Photochem. Rev. 11, 1 (2010)

    Article  Google Scholar 

  2. T. Tsujioka, M. Shimizu, E. Ishihara, Appl. Phys. Lett. 87, 213506 (2005)

    Article  ADS  Google Scholar 

  3. P. Zachaias, M.C. Gather, A. Koehnen, N. Rehmann, K. Meerholz, Angew. Chem. 121, 4098 (2009)

    Article  Google Scholar 

  4. P. Anderson, N.D. Robinson, M. Berggren, Adv. Mater. 17, 1798 (2005)

    Article  Google Scholar 

  5. R. Hayakawa, K. Higashiguchi, K. Matsuda, T. Chikyow, Y. Wakayama, ACS Appl. Mater. Interfaces 5, 3625 (2013)

    Article  Google Scholar 

  6. Z. Zhang, X. Liu, Z. Li, Z. Chen, F. Zhao, F. Zhang, C.-H. Tung, Adv. Funct. Mater. 18, 302 (2008)

    Article  Google Scholar 

  7. R.C. Shallcross, P. Zacharias, A. Koehnen, P.O. Koerner, E. Maibach, K. Meerholz, Adv. Mater. 25, 469 (2013)

    Article  Google Scholar 

  8. T. Tsujioka, T. Sasa, Y. Kakihara, Org. Electron. 13, 681 (2012)

    Article  Google Scholar 

  9. M. Irie, Chem. Rev. 100, 1685 (2000)

    Article  Google Scholar 

  10. W.R. Browne, B.L. Feringa, Annu. Rev. Phys. Chem. 60, 407 (2009)

    Article  ADS  Google Scholar 

  11. S. Tanaka, M. Toba, T. Nakashima, T. Kawai, K. Yoshino, Jpn. J. Appl. Phys. 47, 1215 (2008)

    Article  ADS  Google Scholar 

  12. E. Orgiu, N. Crivillers, M. Herder, L. Grubert, M. Paetzel, J. Frisch, E. Pavlica, D.T. Duong, G. Bratina, A. Salleo, N. Koch, S. Hecht, P. Samorì, Nat. Chem. 4, 675 (2012)

    Article  Google Scholar 

  13. C. Adamo, V. Barone, J. Chem. Phys. 110, 6158 (1999)

    Article  ADS  Google Scholar 

  14. N. Koch, ChemPhysChem 8, 1438 (2007)

    Article  Google Scholar 

  15. B. Broeker, R.P. Blum, J. Frisch, A. Vollmer, O.T. Hofmann, R. Rieger, K. Muellen, J.P. Rabe, E. Zojer, N. Koch, Appl. Phys. Lett. 93, 243303 (2008)

    Article  ADS  Google Scholar 

  16. N. Koch, S. Duhm, J.P. Rabe, S. Rentenberger, R.L. Johnson, J. Klankermayer, F. Schreiber, Appl. Phys. Lett. 87, 101905 (2005)

    Article  ADS  Google Scholar 

  17. J. Frisch, A. Vollmer, J.P. Rabe, N. Koch, Org. Electron. 12, 916 (2011)

    Article  Google Scholar 

  18. X. Cheng, Y.-Y. Noh, J. Wang, M. Tello, J. Frisch, R.-P. Blum, A. Vollmer, J.P. Rabe, N. Koch, H. Serringhaus, Adv. Mater. 19, 2407 (2009)

    Google Scholar 

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Acknowledgements

This work was supported by the SPP1355 and the SFB658 of the DFG and the Helmholtz-Energie-Allianz ‘Hybrid-Photovoltaik’. We thank Juergen P. Rabe for providing access to a photoemission setup.

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Correspondence to Norbert Koch.

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Frisch, J., Herder, M., Herrmann, P. et al. Photoinduced reversible changes in the electronic structure of photochromic diarylethene films. Appl. Phys. A 113, 1–4 (2013). https://doi.org/10.1007/s00339-013-7892-z

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  • DOI: https://doi.org/10.1007/s00339-013-7892-z

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