Optical Properties of Three Differently Colored Crystal Modifications of a 2,3-Dicyanopyrazine Dye

Okada, Naoya; Eto, Ryohei; Horiguchi-Babamoto, Emi; Kobayashi, Takashi; Naito, Hiroyoshi; Shiro, Motoo; Takahashi, H.; Matsumoto, Shinya

doi:10.1246/bcsj.20140409

Cited by 6 publications

(3 citation statements)

References 28 publications

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“…Several AQ dyes bearing different amino and hydroxy donor moieties were selected and their electronic properties were investigated experimentally and theoretically (PM5/RPA, 13,14,46 ZINDO/CI 47,48 and TD-DFT). 49 The positions of non-hydrogen atoms were based on the atomic coordinates from the obtained structural data and the positions of hydrogen atoms were normalised using Mercury 4.2.0 50 in all calculations.…”

Section: Methodsmentioning

confidence: 99%

Comparison of semi‐empirical and density functional approaches for the colour and constitution of anthraquinone dyes using X‐ray structure

Hwang

Kim

Matsumoto

2022

Coloration Technology

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Theoretical calculations with density functional theory, semi-empirical PM5 random phase approximation and Zerner's intermediate neglect of differential overlap CI were carried out for various amino and hydroxy anthraquinones using X-ray structure data. Comparing quantum chemical calculation results based on X-ray structure, the PM5 random phase approximation method was the most promising for the prediction of λ max for anthraquinone dyes among the computational methods studied here. From the results of calculated gross population, p z , it was found that the value of p z using the time-dependent density functional theory method was greater than the values calculated by semi-empirical methods. The overestimation of p z could be attributed to the incorrect density functional theory calculation results. The results of PM5 random phase approximation-calculated oscillator strength and torsion angle showed reasonable agreement with the observed results for sterically hindered anthraquinone dyes.

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Section: Methodsmentioning

confidence: 99%

Comparison of semi‐empirical and density functional approaches for the colour and constitution of anthraquinone dyes using X‐ray structure

Hwang

Kim

Matsumoto

2022

Coloration Technology

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“…Exciton interactions [40,41] and molecular deformations [42,43] play an important role in the colour change of organic dyes observed upon crystallisation. In this case, the effect of exciton interaction, which is inversely proportional to the cube of the distance between two dipoles in a dipole approximation [44], was expected to be small due to the relatively large distance between neighbouring chromophores (Table S3).…”

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confidence: 99%

A variety of solid-state fluorescence properties of pyrazine dyes depending on terminal substituents

et al. 2017

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The optical properties of 2,5-diamino-3,6-dicyanopyrazine derivatives bearing singly methyl-or halogen-substituted benzyl groups were studied in both solution and crystalline phases. In solution, all derivatives showed similar absorption and fluorescence properties, since the electronic state of their fluorophore was not altered by substituents attached to the benzyl groups. In contrast, crystalline compounds exhibited a variety of fluorescence colours (yellow, orange, and red), since their solid-state absorption and fluorescence properties were correlated with a change in the electron-donating ability of amino groups due to crystallisation. The absolute fluorescence quantum yields of crystalline dyes (0.14−0.91) showed broad variability, depending on the nature and positions of terminal substituents.

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“…Furthermore, pyrazine derivatives are easily functionalised by substitution of donor groups at the 2, 3, 5, 6-positions, resulting in a small CT state with a separation of the HOMO and the LUMO [15]. Some pyrazine dyes have been reported to exhibit several different solid forms with different optical properties [16][17][18]. 2,5-Diamino-3,6-dicyanopyrazine (1) shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of liquid pyrazine dyes

et al. 2020

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Optical Properties of Three Differently Colored Crystal Modifications of a 2,3-Dicyanopyrazine Dye

Cited by 6 publications

References 28 publications

Comparison of semi‐empirical and density functional approaches for the colour and constitution of anthraquinone dyes using X‐ray structure

Comparison of semi‐empirical and density functional approaches for the colour and constitution of anthraquinone dyes using X‐ray structure

A variety of solid-state fluorescence properties of pyrazine dyes depending on terminal substituents

Synthesis and properties of liquid pyrazine dyes

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