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
N. Y. C. Chu, in Photochromism: Molecules and Systems, ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, ch. 10, p. 493
N. Y. C. Chu, in Photochromism: Molecules and Systems, ed. H. Dürr and H. Bouas-Laurent, Elsevier, Amsterdam, 1990, ch. 24, p. 879.
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.
V. Lokshin, A. Samat and A. V. Metelitsa, Spirooxazines: synthesis, structure, spectral and photochromic properties, Russ. Chem. Rev., 2002, 71, 893–916.
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.
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.
M. Irie, Diarylethenes for memories and switches, Chem. Rev., 2000, 100, 1685–1716.
J. A. Delaire and K. Nakatani, Linear and nonlinear optical properties of photochromic molecules and materials, Chem. Rev., 2000, 100, 1817–1845.
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.
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.
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.
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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