New green emitters based on push-pull type pyrene substituted cyanopyridones: Design strategies and utilization in organic light-emitting diodes

Vishrutha, K.S.; Ulla, Hidayath; M., R.; Bhat, Badekai Ramachandra; Adhikari, Airody Vasudeva

doi:10.1016/j.dyepig.2023.111560

Cited by 2 publications

(1 citation statement)

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“…Polycyclic aromatic hydrocarbons (PAHs) featuring large π-conjugated architectures are a significant category of functional materials by virtue of their remarkable photophysical, electrical, and mechanical performances − and have been successfully applied in diverse fields, ranging from organic field-effect transistors, , organic photovoltaic cells, − and organic/quantum dot light-emitting diodes − to fluorescence sensors. − As one of the extensively used and representative families of PAHs, pyrenes are chemically stable and contain four integrated benzene rings with extended π-electron delocalization . The unique flat aromatic scaffold endows pyrenes with salient properties, such as deep blue fluorescence, high charge carrier mobility, and prominent hole injection capacity, making them excellent candidates for organic optoelectronic materials, chemosensors, and bioimaging applications. − However, the fluorescence output of pyrene aggregates is usually inferior to what can be achieved in their respective solutions, and this hampers their potential high-technological application in fluorescence-relevant areas. , The weakened emission in the aggregated state may be attributed to the facile generation of detrimental substances such as excimers, given that the planar structure of pyrene tends to undergo intense intermolecular π–π stacking interactions once aggregated.…”

Section: Introductionmentioning

confidence: 99%

Influence of Steric Effects on the Emission Behavior of Pyrene-Based Blue Luminogens

Xie,

Liu,

Liu

et al. 2024

J. Org. Chem.

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Pyrene-based derivatives have been widely deployed in organic luminescent materials because of their bright fluorescence, high charge carrier mobility, and facile modification. Nevertheless, the fluorescence output of conventional pyrenes is prone to quenching upon aggregation due to extensive intermolecular π−π stacking interactions. To address this issue, a set of new Y-shaped pyrene-containing luminogens are synthesized from a new bromopyrene chemical precursor, 2-hydroxyl-7-tertbutyl-1,3-bromopyrene, where the bromo and hydroxyl groups at the pyrene core can be readily modified to obtain the target products and provide great flexibility in tuning the photophysical performances. When the hydroxy group at the 2-position of pyrene was replaced by a benzyl group, the steric hindrance of the benzyl group not only efficiently inhibits the detrimental intermolecular π−π stacking interactions but also rigidifies the molecular conformation, resulting in a narrow-band blue emission. Moreover, the TPE-containing compounds 2c and 3c possessed characteristic aggregation-induced emission (AIE) properties with fluorescence quantum yields of up to 66% and 38% in the solid state, respectively. Thus, this article has methodically investigated the factors influencing the optical behavior, such as intermolecular interactions, and the steric effects of the substituent group, thereby opening up the potential to develop narrow-band pyrene-based blue emitters for OLED device applications.

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