The first representatives of thiophene derivatives with two fulgimide fragments in one molecule have been obtained by the condensation of (3Z)-3-[1-(2,5-dimethyl-3-thienyl)ethylidene]-4-isopropylidene-2,5-furandione with aromatic diamines. The photochromic properties of the obtained compounds have been investigated and the effect of a spacer, linking the two fulgimide fragments, on the reaction rates of photocoloration and photodecoloration of these compounds has been studied.
Similar content being viewed by others
References
Y. Yokoyama, Chem. Rev., 100, 1717 (2000).
M. A. Fox and J. R. Hurst, J. Am. Chem. Soc., 106, 7626 (1984).
I. Willner, S. Rubin, J. Wonner, F. Effenberger, and P. Bäuerle, J. Am. Chem. Soc., 114, 3150 (1992).
H. G. Heller, GB Pat. 1464603; Chem. Abstr., 84, 166263 (1976).
A. Kaneko, A. Tomoda, M. Ishizuka, H. Suzuki, and R. Matsushima, Bull. Chem. Soc. Jpn., 61, 3569 (1988).
A. P. Glaze, S. A. Harris, H. G. Heller, W. Johncock, S. N. Oliver, P. J. Strydom, and J. Whittall, J. Chem. Soc., Perkin Trans. 1, 957 (1985).
C. S. Marvel, R. L. Myers, and J. H. Saunders, J. Am. Chem. Soc., 70, 1694 (1948).
M. Krayushkin, F. Stoyanovich, and S. Shorunov, Mendeleev Commun., 13, 192 (2003).
L. A. Kazitsyna and N. B. Kupletskaya, Application of UV, IR, and NMR Spectroscopy in Organic Chemistry [in Russian], Vysshaya Shkola, Moscow (1971), p. 42.
J. Kiji, T. Okano, H. Kitamura, Y. Yokoyama, S. Kubota, and Y. Kurita, Bull. Chem. Soc. Jpn., 68, 616 (1995).
V. Deblauwe and G. Smets, Makromol. Chem., 189, 2503 (1988).
Ya. L. Gol'dfarb, V. P. Litvinov, and V. I. Shvedov, Zh. Obshch. Khim., 30, 534 (1960).
Ya. A. Levin, and M. S. Skorobogatova, Khim. Geterotsikl. Soedin., 1114 (1967). [Chem. Heterocycl. Comp., 3, 864 (1967)].
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1019-1026, July, 2010.
Rights and permissions
About this article
Cite this article
Luyksaar, S.I., Krayushkin, M.M., Pyankov, Y.A. et al. Synthesis of photochromic bisfulgimides by the condensation of (3Z)-3-[1-(2,5-dimethyl-3-thienyl)-ethylidene]-4-isopropylidene-2,5-furandione with aromatic diamines. Chem Heterocycl Comp 46, 822–828 (2010). https://doi.org/10.1007/s10593-010-0589-8
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-010-0589-8