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 language | English |
---|---|
Pages (from-to) | 2259-2266 |
Number of pages | 8 |
Journal | European Journal of Organic Chemistry |
Volume | 2018 |
Issue number | 19 |
DOIs | |
Publication status | Published - 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