Fluorescence properties of novel 6-butyl-2,3-dicyano-7-methyl-6H-1,4-diazepine styryl dyes containing ethyleneglycol units

Matsui, Masaki; Noguchi, Kazuna; Kubota, Yasuhiro; Funabiki, Kazumasa

doi:10.1016/j.tet.2010.09.103

Cited by 7 publications

(3 citation statements)

References 12 publications

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“…The liquid dyes reported to date are known to exhibit generally low fluorescence quantum yields in the liquid state. [1,2,5,[31][32][33] In contrast, the results presented herein showed that the fluorescence quantum yields in the liquid state of dyes 2g-2i were more intense than those of other liquid derivatives.…”

Section: Uv-vis Absorption and Fluorescence Spectracontrasting

confidence: 85%

Synthesis and properties of liquid pyrazine dyes

et al. 2020

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Section: Uv-vis Absorption and Fluorescence Spectracontrasting

confidence: 85%

Synthesis and properties of liquid pyrazine dyes

et al. 2020

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“…Therefore, oxaalkyl groups can show weaker intermolecular interactions than alkyl groups. In fact, the melting point, which reflects the degree of intermolecular interactions, of oxaalkyl derivatives is lower than that of the alkyl derivatives 6) . Though many kinds of cationic styryl dyes are known, no liquid derivatives have been reported so far.…”

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confidence: 93%

“…2-Methylpyridine (1) was purchased from Nacalai tesque, Inc. Lithium bis(perfluorobutylsulfonyl)imide (16) were purchased from Wako Chemical Industries, Ltd. 4-[Bis(2-oxa-4-butanyl)amino]benzaldehyde (8), 4-[bis(2,5-dioxa-7-heptanyl)amino]benzaldehyde (9), and 4-[bis(2,5,8-trioxa-10-octadecanyl)amino]benzaldehyde (10) were prepared as described in the literature 6) .…”

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confidence: 99%

Liquid 2-Pyridinium Styryl Dyes having Oxaalkyl Units

Matsui

Kubota

Funabiki

2014

Journal of the Japan Society of Colour Material

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Dyes and pigments, in which auxochromes such as amino, nitro, and hydroxyl groups are attached in a molecule, are usually solid. In principle, as organic dyes are aromatic compounds, they have strong π/π interactions in the solid state. Furthermore, these auxochromes can give strong polarity to the molecule and/or form hydrogen bonding to show high melting point. Recently, we have reported that any 7-substituted coumarins are liquid at room temperature 1) . Pyridinium cations and bis(perfluoroalkylsulfonyl)imide anions are important components of ionic liquids 2-4) . We consider that even polar cationic dyes in which these ionic liquid components are contained have potentials for liquid derivatives. In our previous paper, 2-[4-(didecylamino)styryl]-1-dodecylpyridinium bis(perfluorobutylsulfonyl)imide was reported to show very low melting point of 27.2 ˚C 5) . In the case of alkyl groups, Van der Walls interactions exist between them. Meanwhile, oxaalkyl groups have intermolecular repulsion between the oxygen atoms due to lone electron pairs on the oxygen atom(s). Therefore, oxaalkyl groups can show weaker intermolecular interactions than alkyl groups. In fact, the melting point, which reflects the degree of intermolecular interactions, of oxaalkyl derivatives is lower than that of the alkyl derivatives 6) . Though many kinds of cationic styryl dyes are known, no liquid derivatives have been reported so far. On the basis of these points, though practical applications of liquid dyes have not been found yet, we hereby report the preparation of liquid styryl dyes in this paper.Melting points were measured with a Yanagimoto MP-S2 micro-melting-point apparatus and SII Technology Co., EXSTAR-6000 instrument. NMR spectra were obtained by a JMN α-400 spectrometer. IR spectra were taken by a Shimadzu Affinity-1 spectrophotometer. UV-vis absorption and fluorescence spectra were taken on Hitachi U-3500 and JASCO FP8600 spectrophotometers, respectively. Fluorescence quantum yields were measured by a Hamamatsu Photonics Quantaurus QY C11347-01.2-Methylpyridine (1) was purchased from Nacalai tesque, Inc. Lithium bis(perfluorobutylsulfonyl)imide (16) were purchased from Wako Chemical Industries, Ltd. 4-[Bis(2-oxa-4-butanyl)amino]benzaldehyde (8), 4-[bis(2,5-dioxa-7-heptanyl)amino]benzaldehyde (9), and 4-[bis(2,5,8-trioxa-10-octadecanyl)amino]benzaldehyde (10) were prepared as described in the literature 6) .To an acetonitrile solution (10 mL) of 2-methylpyridine (1) (0.93 g, 10 mmol) was added oxaalkyl tosylates 2-4 (12 mmol). The mixture was refluxed for 2 days. After the reaction was completed, the reaction mixture was poured into ether. The resulting precipitate was washed with ether and dried. The product was used without further purification. The physical and spectral data are shown below. 2-Methyl-1-(2-oxa-4-butanyl)pyridinium tosylate (5)Yield 92 21.2, 57.6, 59.0, 71.0, 125.86. 125.86 (2C), 128.6 (2C), 129.3, 139.2, 143.5, 144.7, 147.0, 155.7; IR (KBr) ν = 1521, 1478, 1457, 1208, 1192, 1121 Anal. Found: C, 59.51; H, ...

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Crystal Structures and Emitting Properties of Trifluoromethylaminoquinoline Derivatives: Thermal Single‐Crystal‐to‐Single‐Crystal Transformation of Polymorphic Crystals That Emit Different Colors

Abe

Karasawa

Koga

2012

Chemistry A European J

102

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2,4-Trifluoromethylquinoline (TFMAQ) derivatives that have amine (1), methylamine (2), phenylamine (3), and dimethylamine (4) substituents at the 7-position of the quinoline ring were prepared and crystallized. Six crystals including the crystal polymorphs of 2 (crystal GB and YG) and 3 (crystal B and G) were obtained and characterized by X-ray crystallography. In solution, TFMAQ derivatives emitted relatively strong fluorescence (lambda(max)(f)=418-469 nm and Φ(f)(s)=0.23-0.60) depending on the solvent polarity. From Lippert-Mataga plots, Δμ values in the range of 7.8-14 D were obtained. In the crystalline state, TFMAQ derivatives emitted at longer wavelengths (lambda(max)(f)=464-530 nm) with lower intensity (Φ(f)(c)=0.01-0.28) than those in n-hexane solution. The polymorphous crystals of 2 and 3 emitted different colors: 2, lambda(max)(f)=470 and 530 nm with Φ(f)(c)=0.04 and approximately 0.01 for crystal GB and YG, respectively; and 3, lambda(max)(f)=464 and 506 nm with Φ(f)(c)=0.28 and approximately 0.28 for crystal B and G, respectively. In both crystal polymorphs of 2 and 3, crystals GB and G showed emission color changes by heating/melting/cooling cycles that were representative. By following the color changes in heating at the temperature below the melting point with X-ray diffraction measurements and X-ray crystallography, the single-crystal-to-single-crystal transformations from crystal GB to YG for 2 and from crystal B to G for 3 were revealed.

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Fluorescence properties of novel 6-butyl-2,3-dicyano-7-methyl-6H-1,4-diazepine styryl dyes containing ethyleneglycol units

Cited by 7 publications

References 12 publications

Synthesis and properties of liquid pyrazine dyes

Synthesis and properties of liquid pyrazine dyes

Liquid 2-Pyridinium Styryl Dyes having Oxaalkyl Units

Crystal Structures and Emitting Properties of Trifluoromethylaminoquinoline Derivatives: Thermal Single‐Crystal‐to‐Single‐Crystal Transformation of Polymorphic Crystals That Emit Different Colors

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