Design, synthesis, and characterization of α,ω-disubstituted indeno[1,2-b]fluorene-6,12-dione-thiophene molecular semiconductors. Enhancement of ambipolar charge transport through synthetic tailoring of alkyl substituents

摘要: A series of indeno[1,2-b]fluorene-6,12-dione-thiophene derivatives with hydrocarbon substituents at α,ω-positions as side groups have been designed and synthesized. The new compounds were fully characterized by 1H/13C NMR, mass spectrometry, cyclic voltammetry, UV-vis absorption spectroscopy, differential scanning calorimetry, thermogravimetric analysis, melting point measurements. solid state structure the indeno[1,2-b]fluorene-6,12-dione acceptor core has identified based on single-crystal X-ray diffraction (XRD). structural electronic properties also studied using density functional theory calculations, which found to be in excellent agreement experimental findings provided further insight. detailed effects alkyl chain size orientation optoelectronic properties, intermolecular cohesive forces, thin-film microstructures, charge transport performance semiconductors investigated. Two solution-processable semiconductors, 2EH-TIFDKT 2OD-TIFDKT, deposited thin-films via solution-shearing, drop-casting, droplet-pinned crystallization methods, their morphologies microstructures investigated (XRD) atomic force microscopy (AFM). solution-processed transistors 2OD-TIFDKT showed ambipolar device operations electron hole mobilities high 0.12 cm2 V−1 s−1 0.02 s−1, respectively, Ion/Ioff ratios 105 106. Here, we demonstrate that rational repositioning β-substituents molecular termini greatly benefits π-core planarity while maintaining a good solubility, results favorable characteristics for more efficient charge-transport solid-state. carrier increased two–three orders magnitude account side-chain engineering.