Perfluorophenyl‐Perfluorophenyl Stacking‐Promoted Aggregation‐Induced Emission Enhancement of Crystalline 5‐Aryloxy‐3<i>H</i>‐Indole

Funabiki, Kazumasa; Yamada, Kengo; Matsueda, Hisaki; Arisawa, Yuta; Agou, Tomohiro; Kubota, Yasuhiro; Inuzuka, Toshiyasu; Wasada, Hiroaki

doi:10.1002/ejoc.202001638

Cited by 2 publications

(2 citation statements)

References 33 publications

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“…However, sequential π F −π F stacking was noted between the two perfluoronaphthalene rings; the distance between them is 3.303 Å (Figure 9a). 21 Because the two phenyl groups on the nitrogen atom of 3c are not bonded, individual 3c molecules can smoothly approach one another, resulting in sequential π F −π F stacking of the perfluoronaphthalene rings. Not only the absence of π−π stacking between the phenyl groups of the donor moiety but also π F −π F stacking-induced formation of Htype aggregation seemed to cause a dramatic decrease in the Φ f of 3c.…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 85%

Design, Regioselective Synthesis, and Photophysical Properties of Perfluoronaphthalene-Based Donor–Acceptor–Donor Fluorescent Dyes

et al. 2022

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A one-step route to a series of perfluoronaphthalene-based donor (D)−acceptor (A)−D fluorescent dyes with various electron-donating groups was developed. The perfluoronaphthalene moiety in the D−A−D dyes served as a good electron-accepting aromatic ring with excellent intramolecular charge transfer properties, as determined by density functional theory calculations and measurements of the fluorescence properties in solution, in poly(methyl methacrylate) (PMMA) films, and in crystal form. Notably, replacing the naphthalene ring with perfluoronaphthalene in the D−A−D dyes carrying the phenothiazine moiety not only stabilized the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels but also reduced the energy band gap to change the emission color from blue to yellow. Among the four synthesized perfluoronaphthalene D−A−D dyes, those bearing diphenylamino groups afforded the best fluorescence quantum yields in Et 2 O solution (0.60) and in PMMA film (0.65) because the propeller structure of the diphenylamino group that acts as a donor substituent effectively suppresses radiation-free deactivation. In contrast, in the crystalline state, the carbazoyl-bearing D−A−D dye provided the best fluorescence quantum yield (0.35) because the radiation-free inactivation was suppressed by π−π F stacking at the donor site, which was confirmed by single-crystal X-ray analysis.

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Section: The Journal Of Organic Chemistrymentioning

confidence: 85%

Design, Regioselective Synthesis, and Photophysical Properties of Perfluoronaphthalene-Based Donor–Acceptor–Donor Fluorescent Dyes

et al. 2022

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“…Compounds with perfluoroaromatic motifs are of interest for the design of fluorescence materials, including their application in optoelectronic devices (Funabiki et al, 2021;Feng et al, 2021;Moseev et al, 2019;Kandhadi et al, 2018;Lukes ˇet al, 2016;Wang et al, 2013;Matsui et al, 2008). For instance, the perfluorobiphenyl moiety was used as an electron acceptor for new donor-acceptor compounds with thermally activated delayed fluorescence (TADF) applied for the fabrication of TADF-based OLEDs (Danyliv et al, 2021;Hladka et al, 2018).…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone

Pokhodylo¹,

Slyvka²,

Goreshnik³

et al. 2021

Acta Cryst E

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The title compound, C17H7F8N3O, was obtained via the reaction of 1-azido-2,3,4,5,6-pentafluorobenzene with 4,4,4-trifluoro-1-(p-tolyl)butane-1,3-dione using triethylamine as a base catalyst and solvent. The dihedral angles between the pentafluorophenyl (A), triazole (B) and p-tolyl (C) rings are A/B = 62.3 (2), B/C = 43.9 (3) and A/C = 19.1 (3)°. In the crystal, the molecules are linked by C—H...F and C—H...O hydrogen bonds as well as by aromatic π–π stacking interactions into a three-dimensional network. To further analyse the intermolecular interactions, a Hirshfeld surface analysis was performed.

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Perfluorophenyl‐Perfluorophenyl Stacking‐Promoted Aggregation‐Induced Emission Enhancement of Crystalline 5‐Aryloxy‐3H‐Indole

Cited by 2 publications

References 33 publications

Design, Regioselective Synthesis, and Photophysical Properties of Perfluoronaphthalene-Based Donor–Acceptor–Donor Fluorescent Dyes

Design, Regioselective Synthesis, and Photophysical Properties of Perfluoronaphthalene-Based Donor–Acceptor–Donor Fluorescent Dyes

Synthesis, crystal structure and Hirshfeld surface analysis of (4-methylphenyl)[1-(pentafluorophenyl)-5-(trifluoromethyl)-1H-1,2,3-triazol-4-yl]methanone

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