A Concise and Efficient Route to Electron-Accepting 2,2′-[2,2′-Arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles

Denis S. Baranov, Mikhail N. Uvarov, Maxim S. Kazantsev, Evgeni M. Glebov, Danil A. Nevostruev, Evgeny A. Mostovich, Olga V. Antonova, Leonid V. Kulik

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A concise organolithium-free route to build electron-accepting molecules consisting of two 2-(11-oxoanthra[1,2-b]thiophen-6-ylidene)propanedinitrile units connected by functionalized π-conjugated linkers was developed. Annulation of two thiophene rings in one step was achieved through chemoselective cyclocondensation of a bis(ethynylanthraquinone) substrate with sodium sulfide. Finally, electron-accepting dicyanomethylene moieties were introduced by Knoevenagel condensation with malodinitrile. The synthesized 2,2′-[2,2′-arenediylbis(11-oxoanthra[1,2-b]thiophene-6-ylidene)]dipropanedinitriles were studied by UV/Vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations. The acceptor properties of these compounds were confirmed by efficient light-induced electron transfer in their blend with a donor polymer, poly(3-hexylthiophene-2,5-diyl), detected by electron paramagnetic resonance spectroscopy.

Original languageEnglish
Pages (from-to)2259-2266
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number19
DOIs
Publication statusPublished - 24 May 2018

Keywords

  • Annulation
  • Electron-deficient compounds
  • Functional organic materials
  • Fused-ring systems
  • Polycycles
  • Quinones
  • Sulfur heterocycles
  • PERFORMANCE ORGANIC SEMICONDUCTORS
  • SOLAR-CELLS
  • SMALL MOLECULES
  • NON-FULLERENE ACCEPTORS
  • LIGHT-INDUCED EPR
  • FIELD-EFFECT TRANSISTORS
  • ASYMMETRIC LINEAR ACENES
  • ACETYLENIC DERIVATIVES
  • BASIS-SETS
  • SODIUM SULFIDE

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