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Synthesis, Characterization and Photochromic Properties of Novel Spirooxazines
Corresponding Author(s) : Hong-Jun Zhu
Asian Journal of Chemistry,
Vol. 25 No. 5 (2013): Vol 25 Issue 5
Abstract
A series of spirooxazine compounds were synthesized via condensation reaction of 1,3,3- trimethyl-2-methyleneindoline with ortho-hydroxynitroso aromatic derivatives, then esterification with acyl chlorides. Their structures were confirmed by FTIR, 1H NMR, 13C NMR and elemental analyses. Absorption bands in the visible region were observed in UV-VIS absorption spectra (lmax: 530-665 nm), which were red-shifted as the polarity of solvent increased. Furthermore, these absorption bands also red-shifted with the increase of the electron-donating ability of the 6'-heterocycle substituent, but were nearly unaffected by 9'-acyloxy. The experimental results of thermal decoloration showed that the thermal relaxation progress of the photomerocyanine followed first order kinetics and the relaxation time was tuned in a broad range from 125-1886 s (at 20 ºC) by changing electron-donating power on 6'-heterocycle and 9'-acyloxy, these provided a new design strategy to synthesize photochromic molecules which features different and acceptable relaxation time.
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References
V.A. Lokshin, A. Samat and A.V. Metelitsa, Russ. Chem. Rev., 71, 893 (2002).
N. Alhashimy, R. Byrne, S. Minkovska and D. Diamond, Tetrahedron Lett., 50, 2573 (2009).
Y.A. Son, Y.M. Park, M.S. Choi and S.H. Kim, Dyes Pigments, 75, 279 (2007).
D. Gust, T.A. Moore and A.L. Moore, Chem. Commun., 1169 (2006).
H. Tian and S.J. Yang, Chem. Soc. Rev., 33, 85 (2004).
S. Kawata and Y. Kawata, Chem. Rev., 100, 1777 (2000).
T. Deligeorgiev, S. Minkovska, B. Jeliazkova and S. Rakovsky, Dyes Pigments, 53, 101 (2002).
G. Berkovic, V. Krongauz and V. Weiss, Chem. Rev., 100, 1741 (2000).
S. Minkovska, B. Jeliazkova, E. Borisova, L. Avramov and T. Deligeorgiev, J. Photochem. Photobiol. A, 163, 121 (2004).
P. Rys, R. Weber and Q.L. Wu, Can. J. Chem., 71, 1828 (1993).
E.U. Kulawardana, T. Kuruwita-Mudiyanselage and D.C. Neckers, J. Polym. Sci. A: Polym. Chem., 47, 3318 (2009).
H. Dürr, Y. Ma and G. Corterllaro, Synthesis, 294 (1995).
T.F. Tan, P.L. Chen, H.M. Huang and J.B. Meng, Tetrahedron, 61, 8192 (2005).
M. Rickwood, S.D. Marsden, M.E. Ormsby, A.L. Staunton and D.W. Wood, Mol. Cryst. Liq. Cryst., 246, 17 (1994)