Synthesis and properties of triphenylamine-based hydrazones with reactive vinyl groups

Two triphenylamine-based hydrazones with reactive vinyl groups were synthesized and characterized. The optical, thermal, electrochemical and photoelectrical properties of the obtained compounds were studied. All the synthesized hydrazone monomers form glasses with the glass transition temperatures ranging from 52 °C to 82 °C. The electron photoemission spectra of the synthesized hydrazones were recorded and ionization potentials of 5.22–5.29 eV were established. Room temperature hole-drift mobilities in the amorphous film of hydrazone monomer having three vinyl groups established by xerographic time-of-flight technique was found to be 3.5 × 10−3 cm2/V·s at an electric field of 6.4 × 105 cm2/V·s. Self-polymerization of the hydrazones bearing vinyl groups was demonstrated by differential scanning calorimetry. Self-polymerization of monomers containing one and three vinyl groups started at 151 °C and 136 °C, while maximum polymerization rates were observed at 209 °C and 167 °C respectively.

► Triphenylamine-based hydrazones with reactive vinyl groups.
► Ionization potentials of the solid samples 5.22–5.29 eV.
► Hole-drift mobility of 3.5 × 10−3 cm2/V·s at an electric field of 6.4 × 105 cm2/V·s.
► Self-polymerization demonstrated by differential scanning calorimetry.