Novel fluorophores based on imidazopyrazine derivatives: Synthesis and photophysical characterization focusing on solvatochromism and sensitivity towards nitroaromatic compounds

• Published in: Dyes and pigments 2019-09, Vol.168, p.248-256
• Main Authors: Verbitskiy, Egor V., Kvashnin, Yuriy A., Baranova, Anna A., Khokhlov, Konstantin O., Chuvashov, Roman D., Yakovleva, Yuliya A., Makarova, Nadezhda I., Vetrova, Elena V., Metelitsa, Anatoly V., Rusinov, Gennady L., Chupakhin, Oleg N., Charushin, Valery N.
• Format: Article
• Language: English
• Subjects: Fluorescence quenching; Imidazole; Nitroaromatic compounds; Pyrazine; Solvatochromism
• ISSN: 0143-7208; 1873-3743
• DOI: 10.1016/j.dyepig.2019.04.073

Novel imidazopyrazine-based dyes of the D–A type, possessing (hetero)aryl electron-donating groups in the imidazole moiety, have been synthesized. Their photophysical properties have been investigated using absorption and emission spectral analyses, both in solution and in solid-state. All dyes exhibit strong emission solvatochromism (Δλem = 146–201 nm) and possess quantum yields up to 0.28, depending on their molecular structure and solvent polarity. Meanwhile, fluorescence studies have shown that emission of all fluorophores is sensitive towards different nitroaromatic compounds, either in solutions or in a vapor phase. Thus, these compounds can be regarded as promising multifunctional chemosensors. To create your abstract, type over the instructions in the template box below.Fonts or abstract dimensions should not be changed or altered. [Display omitted] •Three D–A type dyes on the basis of imidazopyrazine derivatives were characterized.•The dyes act as “naked eye” colorimetric chemosensors towards polarity of solvents.•The fluorophores can sensitively detect nitroaromatics both in solutions or in a vapors.•The original device « Zaslon-M » for detecting of explosives in vapor phase has been tested.