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Photoinduced shape changes of diarylethene single crystals: correlation between shape changes and molecular packing

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Abstract

Correlation between the photoinduced shape changes of diarylethene single crystals and their molecular packing in the crystals was studied. Crystals of 1,2-bis(5-ethyl-2-phenyl-4-thiazolyl)perfluorocyclopentene (3a) and 1,2-bis(2-isopropyl-5-phenyl-3-thienyl)perfluorocyclopentene (4a) showed similar photoinduced deformation from square to lozenge as that of 1,2-bis- (2-ethyl-5-phenyl-3-thienyl)perfluorocyclopentene (1a). Although these three diarylethenes have different electronic structures and exhibit different colours upon UV irradiation, the crystallographic structures and molecular packing of the crystals are very similar to each other. The result indicates that the deformation mode is determined by the packing mode of component molecules in the crystal. X-Ray crystallographic analysis of a micrometre-sized crystal 1a (20 × 15 × 8 μm) prepared by sublimation revealed that the small-size crystal, which shows photoinduced deformation, has the same crystal structure as that of the large bulk crystal.

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References

  1. M. Whittaker, E. M. Wilson-Kubalek, J. E. Smith, L. Faust, R. A. Milligan and H. L. Sweeney, Nature, 1995, 378, 748.

    Article  CAS  Google Scholar 

  2. T. Sakamoto, M. R. Webb, E. Forgacs, H. D. White and J. R. Sellers, Nature, 2008, 455, 128

    Article  CAS  Google Scholar 

  3. V. Balzani, A. Credi and M. Venturi, Molecular Devices and Machines: Concepts and Perspectives for the Nanoworld, Wiley-VCH, Weinheim, 2008.

    Book  Google Scholar 

  4. E. R. Kay, D. A. Leigh and F. Zerbetto, Angew. Chem., Int. Ed., 2007, 46, 72.

    Article  CAS  Google Scholar 

  5. Y. Liu, A. H. Flood, P. A. Bonvallet, S. A. Vignon, B. H. Northrop, H.-R. Tseng, J. O. Jeppesen, T. J. Huang, B. Brough, M. Baller, S. Magonov, S. D. Solares, W. A. Goddard, C.-M. Ho and J. F. Stoddart, J. Am. Chem. Soc., 2005, 127, 9745.

    Article  CAS  Google Scholar 

  6. H. Finkelmann, E. Nishikawa, G. G. Pereira and M. Warner, Phys. Rev. Lett., 2001, 87, 015501.

    Article  CAS  Google Scholar 

  7. Y. Yu, M. Nakano and T. Ikeda, Nature, 2003, 425, 145.

    Article  CAS  Google Scholar 

  8. S. Kobatake, S. Takami, H. Muto, T. Ishikawa and M. Irie, Nature, 2007, 446, 778.

    Article  CAS  Google Scholar 

  9. M. A. Garcia-Garibay, Angew. Chem., Int. Ed., 2007, 46, 8945

    Article  CAS  Google Scholar 

  10. M. Irie, Bull. Chem. Soc. Jpn., 2008, 81, 917.

    Article  CAS  Google Scholar 

  11. R. O. Al-Kaysi, A. M. Müller and C. J. Bardeen, J. Am. Chem. Soc., 2006, 128, 15938

    Article  CAS  Google Scholar 

  12. R. O. Al-Kaysi and C. J. Bardeen, Adv. Mater., 2007, 19, 1276.

    Article  CAS  Google Scholar 

  13. K. Uchida, S. Sukata, Y. Matsuzawa, M. Akazawa, J. J. D. de Jong, N. Katsonis, Y. Kojima, S. Nakamura, J. Areephong, A. Meetsma and B. L. Ferringa, Chem. Commun., 2008, 326.

    Google Scholar 

  14. H. Koshima, N. Ojima and H. Uchimoto, J. Am. Chem. Soc., 2009, 131, 6890.

    Article  CAS  Google Scholar 

  15. S. Kobatake and M. Irie, Bull. Chem. Soc. Jpn., 2004, 77, 195

    Article  CAS  Google Scholar 

  16. M. Morimoto, S. Kobatake and M. Irie, Chem. Rec., 2004, 4, 23

    Article  CAS  Google Scholar 

  17. M. Morimoto and M. Irie, Chem. Commun., 2005, 3895.

    Google Scholar 

  18. S. Kobatake, K. Uchida, E. Tsuchida and M. Irie, Chem. Lett., 2000, 1340.

    Google Scholar 

  19. A. Mori, A. Sekiguchi, K. Masui, T. Shimada, M. Horie, K. Osakada, M. Kawamoto and T. Ikeda, J. Am. Chem. Soc., 2003, 125, 1700.

    Article  CAS  Google Scholar 

  20. P. Vachal and L. M. Toth, Tetrahedron Lett., 2004, 45, 7157.

    Article  CAS  Google Scholar 

  21. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 1990, 46, 467.

    Article  Google Scholar 

  22. G. M. Sheldrick, SHELXL-97, Program for refinement of crystal structures, University of Göttingen, Germany, 1997.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Motooka 744, Fukuoka, 819-0395, Japan

    Lumi Kuroki

  2. Niihama National College of Technology, Yakumo-cho 7-1, Niihama, Ehime, 792-8580, Japan

    Shizuka Takami

  3. Bruker AXS K.K., Moriya-cho 3-9, Kanagawa-ku, Yokohama, 221-0022, Japan

    Kenji Yoza

  4. Department of Chemistry and Research Center for Smart Molecules, Rikkyo University, Nishi-Ikebukuro 3-34-1, Toshima-ku, Tokyo, 171-8501, Japan

    Masakazu Morimoto & Masahiro Irie

Authors
  1. Lumi Kuroki
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  2. Shizuka Takami
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  3. Kenji Yoza
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  4. Masakazu Morimoto
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  5. Masahiro Irie
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Corresponding author

Correspondence to Masahiro Irie.

Additional information

Electronic supplementary information (ESI) available: Schematic illustration of photocontraction of a crystal and crystal data for 3a, 3a′, 3b, 4a, micro-crystal 1a and micro-crystal 1a′. CCDC reference numbers 713390-713395. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/b9pp00093c

This paper is part of a themed issue on synthetic and natural photoswitches.

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Kuroki, L., Takami, S., Yoza, K. et al. Photoinduced shape changes of diarylethene single crystals: correlation between shape changes and molecular packing. Photochem Photobiol Sci 9, 221–225 (2010). https://doi.org/10.1039/b9pp00093c

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  • DOI: https://doi.org/10.1039/b9pp00093c

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