Abstract
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.
Highlights
The introduction of structures with electron-donating properties to the naphthalene ring allows the obtainment of materials with a low band gap, which is beneficial in optoelectronic applications [11]
Asymmetrical 1,8-naphthalimides structures, constructed from a single imide ring, are often tested as compounds substituted in the 4-C position for organic electronics [1,39,40]
The thermal stability, phase transition temperatures (Tm, Tc ), and glass transition temperatures (Tg ) of bis-(imino-1,8-naphthalimide) derivatives were determined by the thermogravimetric analysis (TGA) and the differential scanning calorimetry (DSC), respectively
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. The imide rings as n-type semiconductors are very popular as electron acceptors with the possibility of functionalizing [1,2,3,4]. Due to their structure, imide rings can be divided into five- and six-membered rings obtained from phthalic or naphthalene/perylene anhydrides. Many publications associated with imide rings in organic electronics include symmetrical structures (phthalic diimides, naphthalene, perylene) [5,6,7,8,9,10]. Asymmetrical 1,8-naphthalimides structures, constructed from a single imide ring, are often tested as compounds substituted in the 4-C position for organic electronics [1,39,40].
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