New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

• Published in: Materials Vol. 14; no. 11; p. 2714
• Main Authors: Kotowicz, Sonia, Korzec, Mateusz, Pająk, Agnieszka Katarzyna, Golba, Sylwia, Małecki, Jan Grzegorz, Siwy, Mariola, Grzelak, Justyna, Maćkowski, Sebastian, Schab-Balcerzak, Ewa
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 21.05.2021; MDPI
• Subjects: 1,8-naphthalimides; Amorphous materials; azomethinediimides; C-3 position; electrochemistry; Electromagnetic radiation; Emission analysis; Light emission; luminescence; Molecular orbitals; Optical properties; Polyvinyl carbazole; Semiconductors
• ISSN: 1996-1944; 1996-1944
• DOI: 10.3390/ma14112714

In this paper, six novel symmetrical bis-(imino-1,8-naphthalimides) differing in core and N-substituent structure were synthesized, and their thermal (TGA, DSC), optical (UV-Vis, PL), electrochemical (DPV, CV) properties were evaluated. The compounds were stable to 280 °C and could be transferred into amorphous materials. Electrochemical investigations showed their ability to occur reductions and oxidations processes. They exhibited deep LUMO levels of about −3.22 eV and HOMO levels above −5.80 eV. The optical investigations were carried out in the solutions (polar and non-polar) and in films and blends with PVK:PBD. Bis-(imino-1,8-naphthalimides) absorbed electromagnetic radiation in the range of 243–415 nm and emitted light from blue to yellow. Their capacity for light emission under voltage was preliminarily tested in devices with an active layer consisting of a neat compound and a blend with PVK:PBD. The diodes emitted green or red light.