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


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Article Info

DATE

2010-05

AUTHORS

S. K. Balenko, N. I. Makarova, V. P. Rybalkin, E. N. Shepelenko, L. L. Popova, V. V. Tkachev, S. M. Aldoshin, A. V. Metelitsa, V. A. Bren’, V. I. Minkin

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. More... »

PAGES

954-959

References to SciGraph publications

  • 1998-09. Fluorescent photochromic fulgides in RESEARCH ON CHEMICAL INTERMEDIATES
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