Synthesis, structures, and photochromic properties of 2-methylthieno[3,2-b][1]benzothiophen-3-ylfulgide |
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| Authors: | S. K. Balenko N. I. Makarova O. G. Karamov V. P. Rybalkin I. V. Dorogan L. L. Popova E. N. Shepelenko A. V. Metelitsa V. V. Tkachev S. M. Aldoshin V. A. Bren V. I. Minkin |
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| Affiliation: | (1) Research Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 prosp. Stachki, 344090 Rostov-on-Don, Russian Federation;(2) Southern Scientific Center of the Russian Academy of Sciences, 41 ul. Chekhova, 344006 Rostov-on-Don, Russian Federation;(3) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432 Chernogolovka, Moscow Region, Russian Federation |
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| Abstract: | ![]()
The novel heterocyclic fulgide, 3-(1-methylethylidene)-4-[1-(2-methylthieno[3,2-b]-[1]benzothiophen-3-yl)ethylidene]dihydrofuran-2,5-dione, was obtained and isolated as a Z-isomer. Its structure was confirmed by electronic absorption spectroscopy, 1H NMR spectroscopy, and X-ray diffraction analysis. The novel thienothiophene fulgide is photochromic in both solutions and the crystalline state. Its colored cyclic form resists photodegradation and is thermally stable. When benzothiophene is annulated with the thienyl fragment, the long-wavelength absorption peak of the cyclic isomer of the novel fulgide experiences a bathochromic shift compared to the earlier described 3-thienylfulgide. The TD B3LYP/6-311G**-calculated spectroscopic characteristics of the fulgide isomers suggest the formation of their photostationary mixture under irradiation with λ = 365 nm. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2318–2324, December, 2007. |
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| Keywords: | thieno[3,2-b][1]benzothiophene fulgide synthesis structure photochromism quantum-chemical calculations density functional theory |
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