Chemistry of Heterocyclic Compounds

, Volume 53, Issue 1, pp 46–53 | Cite as

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

  • Jiří Kulhánek
  • Miroslav Ludwig
  • Filip Bureš
  • Jiří Tydlitát
Article

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.

Keywords

3,4-dinitrothiophene push-pull-push chromophore absorption spectra calculations nonlinear optics 

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Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Jiří Kulhánek
    • 1
  • Miroslav Ludwig
    • 1
  • Filip Bureš
    • 1
  • Jiří Tydlitát
    • 1
  1. 1.Institute of Organic Chemistry and Technology, Faculty of Chemical TechnologyUniversity of PardubicePardubiceCzech Republic

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