Materials (Oct 2022)

Six New Unsymmetrical Imino-1,8-naphthalimide Derivatives Substituted at 3-C Position—Photophysical Investigations

  • Sonia Kotowicz,
  • Mateusz Korzec,
  • Jan Grzegorz Małecki,
  • Sylwia Golba,
  • Mariola Siwy,
  • Sebastian Maćkowski,
  • Ewa Schab-Balcerzak

DOI
https://doi.org/10.3390/ma15197043
Journal volume & issue
Vol. 15, no. 19
p. 7043

Abstract

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In this research, six novel unsymmetrical imino-1,8-naphthalimides (AzNI) were synthesized. Comprehensive thermal (thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), optical (UV-Vis, photoluminescence), and electrochemical (CV, DPV) studies were carried out to characterize these new compounds. The molecules showed the onset of thermal decomposition in the temperature range 283–372 °C and molecular glass behavior. Imino-1,8-naphthalimides underwent reduction and oxidation processes with the electrochemical energy band gap (Eg) below 2.41 eV. The optical properties were evaluated in solvents with different polarities and in the solid-state as a thin films and binary blends with poly(N-vinylcarbazole): (2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole) (PVK:PBD). Presented compounds emitted blue light in the solutions and in the green or violet spectral range in the solid-state. Their ability to emit light under external voltage was examined. The devices with guest-host structure emitted light with the maximum located in the blue to red spectral range of the electroluminescence band (EL) depending on the content of the AzNI in the PVK:PBD matrix (guest-host structure).

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