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NMR characterisation of photo-electrocyclised structures of a spirooxazine derivative

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Abstract

Three electrocyclised structures (C-DPh, TTC-DPh and CTC-DPh), produced after UV irradiation of a spiro-oxazine linked by a (Z)-ethenic bridge to a 2-methoxy-naphthalene nucleus, have been identified by NMR spectroscopy.

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Notes and references

  1. N. Y. C. Chu, in Photochromism: Molecules and Systems, ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, ch. 10, p. 493

  2. N. Y. C. Chu, in Photochromism: Molecules and Systems, ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, ch. 24, p. 879.

  3. S. Maeda, in Organic Photochromic and Thermodynamic Compounds, ed. J. C. Crano and R. J. Guglielmetti, Kluwer Academic/ Plenum Press, New York, 1999, vol. 1, p. 85.

    Google Scholar 

  4. V. Lokshin, A. Samat and A. V. Metelitsa, Spirooxazines: synthesis, structure, spectral and photochromic properties, Russ. Chem. Rev., 2002, 71, 893–916.

    Article  CAS  Google Scholar 

  5. J. Berthet, S. Delbaere, V. Lokshin, S. Samat, R. Guglielmetti and G. Vermeersch, Studies of polyphotochromic behaviour of super-molecules by NMR spectroscopy. Part 1. A bis-spirooxazine with a (Z)-ethenic bridge between each moiety, Photochem. Photobiol. Sci., 2002, 1, 333–339.

    Article  CAS  Google Scholar 

  6. A. Samat, V. Lokshin, K. Chamontin, D. Levi, G. Pepe and R. Guglielmetti, Synthesis and unexpected photochemical behaviour of biphotochromic systems involving spirooxazines and naphtho-pyrans linked by an ethenic bridge, Tetrahedron, 2001, 57, 7349–7359.

    Article  CAS  Google Scholar 

  7. M. Irie, Diarylethenes for memories and switches, Chem. Rev., 2000, 100, 1685–1716.

    Article  CAS  Google Scholar 

  8. J. A. Delaire and K. Nakatani, Linear and nonlinear optical properties of photochromic molecules and materials, Chem. Rev., 2000, 100, 1817–1845.

    Article  CAS  Google Scholar 

  9. S. Delbaere, C. Bochu, N. Azaroual, G. Buntinx and G. Vermeersch, NMR studies of the structure of the photoinduced forms of photochromic spironaphthoxazines, J. Chem. Soc., Perkin Trans. 2, 1997, 1499–1501.

    Google Scholar 

  10. K. Matsuda, S. Yamamoto and M. Irie, Diastereoselective cyclization of a diarylethene having a chiral N-phenylethyl-amide substituent in crystals, Tetrahedron Lett., 2001, 42, 7291–7293.

    Article  CAS  Google Scholar 

  11. J. Berthet, S. Delbaere, D. Levi, P. Brun, R. Guglielmetti and G. Vermeersch, Investigations by NMR spectroscopy of a poly-photochromic system involving two entities, spirooxazine and naphthopyran, linked by a Z-ethenic bridge, J. Chem. Soc., Perkin Trans. 2, 2002, 2118–2124.

    Google Scholar 

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Correspondence to Gaston Vermeersch.

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Berthet, J., Delbaere, S., Lokshin, V. et al. NMR characterisation of photo-electrocyclised structures of a spirooxazine derivative. Photochem Photobiol Sci 2, 978–980 (2003). https://doi.org/10.1039/b306047k

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  • DOI: https://doi.org/10.1039/b306047k

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