3,4-DINITROTHIOPHENE AS A CENTRAL UNIT OF QUADRUPOLAR PUSH-PULL-PUSH SYSTEMS

Authors

  • Jiří Kulhánek University of Pardubice Faculty of Chemical Technology Institute of Organic Chemistry and Technology
  • Miroslav Ludwig University of Pardubice Faculty of Chemical Technology Institute of Organic Chemistry and Technology
  • Filip Bureš University of Pardubice Faculty of Chemical Technology Institute of Organic Chemistry and Technology
  • Jiří Tydlitát University of Pardubice Faculty of Chemical Technology Institute of Organic Chemistry and Technology

DOI:

https://doi.org/10.1007/3495

Keywords:

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

Abstract

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 longest-wavelength 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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Published

2017-01-25

Issue

Vol. 53 No. 1 (2017): Heterocycles in materials chemistry

Section

Original Papers