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3,4-Dinitrothiophene as a central unit of quadrupolar push-pull-push systems

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Chemistry of Heterocyclic Compounds Aims and scope

3,4-Dinitrothiophene has been utilized as a central acceptor unit in quadrupolar D-π-A-π-D push-pull-push chromophores. Employing cross-coupling and Knoevenagel reactions, nine novel chromophores bearing terminal methoxythiophene donor and systematically extended/varied π-linker were synthesized. Optical properties were studied by electronic absorption spectra. Fundamental optoelectronic properties were investigated by semiempirical PM7 calculations. It was shown that by varying the π-conjugated system the longestwavelength absorption maxima can be shifted from 341 to 489 nm. The calculated HOMO–LUMO gaps were found within the range of 6.69–7.29 eV, while the second-order molecular polarizabilities can be tuned from 0.038 to 1.578 × 10–27 esu.

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Correspondence to Jiří Tydlitát.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 42–45

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Kulhánek, J., Ludwig, M., Bureš, F. et al. 3,4-Dinitrothiophene as a central unit of quadrupolar push-pull-push systems. Chem Heterocycl Comp 53, 46–53 (2017). https://doi.org/10.1007/s10593-017-2020-1

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  • DOI: https://doi.org/10.1007/s10593-017-2020-1

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