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A new luminescent azaindole derivative has been designed and synthesized to be implemented in a light-emitting device. The molecular geometry and frontier orbital energy have been investigated by using density functional theory. This newly synthesized molecule emits strongly both in solution and solid state. The fluorescence emission in THF upon addition of an increasing amount of HO has been measured also, displaying an increase of the fluorescence signal which is associated with an aggregation-induced emission phenomenon. Double-layer light-emitting devices including an active layer of the novel emissive material were successfully fabricated. The red-shift of the electroluminescence spectra with respect to the photoluminiscence emission was attributed to the presence of different types of complexes in the emissive material (EM) layer, which are preferentially formed between the nearest-neighbor hole-electron pairs of the electron injection and the EM layers (electroplex).

This study reports on the use of a self-assembling organogel, 5-(4-nonylphenyl)-7-azaindole (1), as a new emitter in small-molecule organic light emitting devices (OLEDs). The theoretical calculations along with the photophysical characterization studies suggest the coexistence of the monomer and dimer species at high concentration of compound 1. The presence of this type of dimer (formed via H-bonding) is responsible for the increased emission. However, the most notable feature is the 3D network of vastly interconnected fibers formed in the organogel that modifies the photophysical properties. Based on this, several OLED architectures are made in order to understand the mechanism involved in the electroluminescence (EL) behavior of 1. Although the position of the EL spectra differs from that of the photoluminescence (PL) spectra, the trends observed in the device properties perfectly match with dimer formation. In this framework a better device performance is associated to a higher efficiency of dimer formation, which optimizes in the OLED prepared from the organogel. Therefore, these results show that the rational combination of a moiety showing a strong PL intensity increased upon aggregation with organogel properties is an efficient strategy to create alternative emitters for OLED devices.

Shape persistent perylene diimide (PDI) multichromophores incorporating ethynylene bridges have been synthesized in high yield via palladium-catalyzed Hagihara coupling, which provides compounds with no rotational or constitutional isomerism in contrast to polyphenylene dendrimers. Their excited-state pathways have been studied at the ensemble and at the single-molecule level and compared to several model compounds. In an apolar solvent, energy hopping and/or energy transfer between the chromophoric units are the dominating processes. In a polar medium, energy hopping is still operative, but electron transfer from the phenyl ethynylene bridge to the chromophore occurs if the former is connected to the bay area of PDI. This effect should be considered when further developing this type of multichromophore, as this nonradiative deactivation process might be unwanted for applications such as optical and electronic devices. At the single-molecule level, the fluorescence intensity traces are characterized by rich on-off dynamics, which we attribute to oxygen-enhanced intersystem crossing leading to the formation of a long-lived dark charge-separated state.