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New V-shaped 2,4-di(hetero)arylpyrimidine push-pull systems: Synthesis, solvatochromism and sensitivity towards nitroaromatic compounds

2018; Elsevier BV; Volume: 159; Linguagem: Inglês

10.1016/j.dyepig.2018.05.075

1873-3743

Egor V. Verbitskiy, Ekaterina M. Dinastiya, Anna A. Baranova, Konstantin O. Khokhlov, Roman D. Chuvashov, Yuliya А. Yakovleva, Nadezhda I. Makarova, E. V. Vetrova, А. В. Метелица, Павел А. Слепухин, Gennady L. Rusinov, О. Н. Чупахин, Valery N. Charushin,

Porphyrin and Phthalocyanine Chemistry

Novel D–π–A–π–D type pyrimidine-based dyes, possessing (hetero)aryl electron-donating groups in 2,4-positions were synthesized, and their photophysical properties were investigated by using absorption and emission spectral analyses. All dyes proved to exhibit a strong emission solvatochromism with quantum yields up to 0.96, depending on their molecular structure and solvent polarity. The compounds have been established to undergo a reversible protonation, directed at nitrogen atoms of the pyrimidine ring, and these phenomena are associated with dramatic color changes. In addition, fluorophores 5a-d show a high sensitive response for nitroaromatic traces in solutions or real-time detection of their vapors in air. These findings indicate that the compounds obtained can be regarded as excellent fluorophores for fluorescent material applications.