Hole-transporting thiophene-based hydrazones with reactive vinyl groups

Synthesis and optical, thermal, electrochemical, and photoelectrical properties of new thiophene-based hydrazones with reactive vinyl groups are reported. The synthesized compounds were characterized by 1H, 13C NMR, IR, UV/vis, fluorescence, mass spectrometries, and cyclic voltammetry. The synthesized thiophene-based hydrazones form glasses with the glass transition temperatures ranging from 15 °C to 72 °C, as it was elucidated by DSC. Cyclic voltammetry measurements showed that all the synthesized dihydrazones are electrochemically stable up to 0.8 V. Their oxidation potentials are in the range of 0.02–0.55 V. Solid state ionization potentials of these compounds were found to be in the range of 4.82–5.35 eV. Time-of-flight hole-drift mobility in the layer of di-(2-(4-vinylbenzyl)-2-phenyl-1-((thiophene-2-yl)methylene))hydrazone approached 10−5 cm2/V s at high electric field.