Hydrazones containing electron-accepting and electron-donating moieties

Hydrazones containing electron-accepting 1,8-naphthalimide species and electron-donating triphenylamino moieties were synthesized and characterized by nuclear magnetic resonance, infrared spectroscopy, and mass spectrometry. Thermal, optical, electrochemical and photophysical properties of the synthesized derivatives were investigated, their, optical and electrochemical band-gap energies and ionization potentials were established. The hydrazones exhibit initial mass loss temperatures in the range of 268–348 °C and can form glasses with glass transition temperatures in the range of 46–142 °C as established by differential scanning calorimetry. Room temperature time-of-flight hole mobilities in the solid solutions of the derivatives in the polymeric host bisphenol-Z polycarbonate (50%) exceeded 10−5 cm2/V s at high applied electric fields.

► Hydrazones containing electron-accepting 1,8-naphthalimide species and electron-donating triphenylamino moieties.
► HOMO energy levels from −5.06 eV to −5.01 eV.
► LUMO energy levels from −3.00 eV to −2.91 eV.
► Ionization potentials of the solid samples 5.45 eV.
► Time-of-flight hole mobilities in the solid solutions of the derivatives in bisphenol-Z polycarbonate (50%) exceed 10−5 cm2/V s.