Novel Y-shaped multi-stimuli responsive pyrene substituted quinoxaline and pyridopyrazine-based push-pull molecules showing solvatochromism, aggregation induced excimer emission, acidofluorochromism and moisture detection

Lamoria, Monika; Milton, Marilyn Daisy

doi:10.1016/j.dyepig.2023.111182

Cited by 13 publications

(2 citation statements)

References 95 publications

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“…THF solutions of the luminogens 2c and 3c both exhibited λ max,abs at 354 nm, while the λ max,abs of 2b and 3b in THF solution was red-shifted to 365 and 368 nm, respectively, which resulted from the better electron donor ability of the TPA group relative to the TPE unit. It is worth noting that the molar extinction coefficient (ε) of 3b and 3c exhibited a significant enhancement compared with 2b and 2c , which was assigned to intramolecular interactions such as C–H···π and/or π–π interactions between the 4-(trifluoromethyl)benzyl segment and the neighboring phenyl group in the TPA and TPE units, leading to an extension of the π-conjugation . Upon irradiation, compounds 2 emitted deep-blue fluorescence in THF solution with the maximum emission peaks located in the range from 408 to 459 nm (Figure B).…”

Section: Resultsmentioning

confidence: 99%

“…It is worth noting that the molar extinction coefficient (ε) of 3b and 3c exhibited a significant enhancement compared with 2b and 2c, which was assigned to intramolecular interactions such as C−H•••π and/ or π−π interactions between the 4-(trifluoromethyl)benzyl segment and the neighboring phenyl group in the TPA and TPE units, leading to an extension of the π-conjugation. 48 Upon irradiation, compounds 2 emitted deep-blue fluorescence in THF solution with the maximum emission peaks located in the range from 408 to 459 nm (Figure 3B). Compound 2b exhibited a large, red-shifted emission compared with 2a and 2c, which was assigned to the stronger electron donor capacity of the TPA unit.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 99%

Section: Photophysical Propertiesmentioning

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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Structurally Diverse Pyrene‐decorated Planar Chiral [2,2]Paracyclophanes with Tunable Circularly Polarized Luminescence between Monomer and Excimer

Lian,

Liu,

et al. 2024

Chemistry A European J

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We reported the synthesis of a series of structurally diverse CPL‐active molecules, in which pyrene units were installed to chiral pm/po‐[2.2]PCP scaffolds either with or without a triple bond spacer for pm/po‐PCP‐P1 and pm/po‐PCP‐P2, respectively. The X‐ray crystallographic analyses revealed that these pyrene‐based [2,2]PCP derivatives exhibited diverse structures and crystal packings in the solid phases. The pyrene‐based [2,2]PCP derivatives exhibit various (chir)optical properties in organic solutions, depending on their respective structures. In a mixture of dioxane and water, pm/po‐PCP‐P1 emit green excimer fluorescence, whereas pm/po‐PCP‐P2 emit blue one. The chiroptical investigation demonstrated that Rp‐pm‐PCP‐P1 and Rp‐pm‐PCP‐P2 exhibited completely opposite CD and CPL signals even they possess the same chiral Rp‐[2.2]PCP core. The same argument also holds for other chiral pyrene‐based [2,2]PCP derivatives. The theoretical calculation revealed that these unusual phenomena were attributed to different orientation between transition electric dipole moments and the magnetic dipole moments originating from the presence or absence of a triple bond spacer. These pyrene‐based [2,2]PCP derivatives display various colors and fluorescence emissions in the solid state and PMMA films, possibly due to the different packings as observed in the crystal structure. Moreover, these compounds also can interact with perylenediimide through π‐π interactions, leading to near‐white fluorescence.

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Modified 2,3-bis(thienyl)quinoxaline fluorophores as potential chemosensors

Moshkina,

Kopotilova,

Gazizov

et al. 2024

Russ Chem Bull

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Novel Y-shaped multi-stimuli responsive pyrene substituted quinoxaline and pyridopyrazine-based push-pull molecules showing solvatochromism, aggregation induced excimer emission, acidofluorochromism and moisture detection

Cited by 13 publications

References 95 publications

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

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

Structurally Diverse Pyrene‐decorated Planar Chiral [2,2]Paracyclophanes with Tunable Circularly Polarized Luminescence between Monomer and Excimer

Modified 2,3-bis(thienyl)quinoxaline fluorophores as potential chemosensors

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