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Synthesis and Photochromic Properties of Asymmetric Dihetarylethenes Based on 5-methoxy-1,2-dimethylindole and 5-(4-bromophenyl)-2-methylthiophene

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Chemistry of Heterocyclic Compounds Aims and scope

We report the synthesis of new asymmetric dihetarylethenes – 4-[5-(4-bromophenyl)-2-methylthiophen-3-yl]-3-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)furan-2,5-dione and 1-alkyl(phenyl)-3-(5-methoxy-1,2-dimethyl-1H-indol-3-yl)-4-[5-(4-bromophenyl)-2-methylthiophen-3-yl]-1H-pyrrole-2,5-diones, which exhibit photo-chromic and fluorescent properties in solution. Thermally stable photoinduced cyclic isomers were observed for dihetarylethenes derived from 5-methoxy-1,2-dimethylindole and 5-(4-bromophenyl)-2-methylthiophene, unlike for their structural analogs based on 5-methoxy-1,2-dimethylindole and unsubstituted thiophene. Changing the thiophene fragment of dihetarylethenes to a 5-(4-bromophenyl)-2-methylthiophene fragment gave rise to photochromic properties in furan-2,5-dione derivatives.

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The authors would like to acknowledge the financial support from the Ministry of Education and Science of the Russian Federation for this work within the framework of baseline of the State Assignment for scientific activity at the Scientific Research Institute of Physical and Organic Chemistry, Southern Federal University (grant 213.01-11/2014-24).

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Correspondence to E. N. Shepelenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1013-1021, July, 2014.

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Shepelenko, E.N., Makarova, N.I., Karamov, O.G. et al. Synthesis and Photochromic Properties of Asymmetric Dihetarylethenes Based on 5-methoxy-1,2-dimethylindole and 5-(4-bromophenyl)-2-methylthiophene. Chem Heterocycl Comp 50, 932–940 (2014). https://doi.org/10.1007/s10593-014-1547-7

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