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Structures and photochromic properties of fulgides based on naphtho[1,2-b]furan and benzo[g]indole

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Abstract

The novel heterocyclic fulgides, i.e. 3-isopropylidene-4-{1-[5-methoxy-1-(4-methoxy-phenyl)-2-methyl-1H-benzo[g]indol-3-yl]ethylidene}dihydrofuran-2,5-dione and 3-isopropylidene-4-[1-(1-benzyl-5-methoxy-2-methyl-1H-benzo[g]indol-3-yl)ethylidene]dihydrofuran-2,5-dione, were prepared and isolated as E-isomers. Photochromism, E-configuration, and high resistance to photocoloration—photobleaching of solutions of these fulgides as well as 3-isopropylidene-4-[1-(5-methoxy-2-methylnaphtho[1,2-b]furan-3-yl)ethylidene]dihydro-furan-2,5-dione and 3-isopropylidene-4-[1-(5-methoxy-2-methyl-1-phenyl-1H-benzo[g]indol-3-yl)ethylidene]dihydrofuran-2,5-dione synthesized previously were shown by X-ray diffraction analysis, 1H NMR spectroscopy and electronic absorption spectroscopy. The novel fulgides show fluorescence and high thermal stability of photogenerated cyclic form. Repeated photo-coloration—photobleaching is accompanied by reversible photoinduced E—Z isomerization. Benzo[g]indolyl fulgides are characterized by the longer wavelength absorption of both original (E) and photoisomeric cyclic (C) forms as compared to naphthofuran fulgide.

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Authors and Affiliations

  1. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090, Rostov-on-Don, Russian Federation

    S. K. Balenko, N. I. Makarova, L. L. Popova, A. V. Metelitsa, V. A. Bren’ & V. I. Minkin

  2. Southern Scientific Center of Russian Academy of Sciences, 41 ul. Chekhova, 344006, Rostov-on-Don, Russian Federation

    V. P. Rybalkin, E. N. Shepelenko, V. A. Bren’ & V. I. Minkin

  3. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. V. Tkachev & S. M. Aldoshin

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  1. S. K. Balenko
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  2. N. I. Makarova
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  3. V. P. Rybalkin
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  4. E. N. Shepelenko
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  5. L. L. Popova
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  6. V. V. Tkachev
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  7. S. M. Aldoshin
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  8. A. V. Metelitsa
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  9. V. A. Bren’
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  10. V. I. Minkin
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Correspondence to S. K. Balenko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 932—938, May, 2010.

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Balenko, S.K., Makarova, N.I., Rybalkin, V.P. et al. Structures and photochromic properties of fulgides based on naphtho[1,2-b]furan and benzo[g]indole. Russ Chem Bull 59, 954–959 (2010). https://doi.org/10.1007/s11172-010-0189-x

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  • DOI: https://doi.org/10.1007/s11172-010-0189-x

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