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Multi-stimuli-responsive fluorescent aminostyrylquinoxalines: Synthesis, solvatochromism, mechanofluorochromism and acidochromism
Dyes and Pigments ( IF 4.1 ) Pub Date : 2018-01-08 , DOI: 10.1016/j.dyepig.2018.01.005
Jinyu Zhao , Jingbo Sun , Oudjaniyobi Simalou , Haoran Wang , Jiang Peng , Lu Zhai , Pengchong Xue , Ran Lu

New D-π-A type aminostyrylquinoxaline derivatives (QDMA1, QDMA2, QTPA1 and QTPA2) were synthesized via Knoevenagel condensation reactions. It was found that their ICT (intramolecular charge transfer) emission were red-shifted significantly with increasing the solvent polarities. Interestingly, compound QTPA2 bearing two terminal triphenylamine groups exhibited reversible mechanofluorochromism. The emission of the as-synthesized crystals of QTPA2 was located at 542 nm, and it was red-shifted to 592 nm upon grinding, so the emitting color was changed from yellow to carmine. Meanwhile, the emission could be recovered when the ground powders were fumed with DCM vapor. XRD patterns and DSC curves in different solid states demonstrated that the mechanofluorochromism was due to the transformation between the crystalline and amorphous states. In addition, the protonation of the synthesized aminostyrylquinoxalines by TFA could lead to the colors of the solutions to change into dark green from yellow, accompanied with the quenching of the emission. Furthermore, we also found that the emission of QTPA2 in the film could be quenched significantly and rapidly stimulated by TFA vapor, and the detection limit and the decay time were estimated to be 167 ppb and 0.47 s, respectively. Therefore, the aminostyrylquinoxaline derivatives could be used as sensory materials to detect acids in solutions and in the films by naked eyes.



中文翻译:

多刺激响应性荧光氨基苯乙烯基喹喔啉:合成,溶剂变色,机械荧光变色和酸致变色

通过Knoevenagel缩合反应合成了新的D-π-A型氨基苯乙烯基啉衍生物(QDMA1QDMA2QTPA1QTPA2)。发现随着溶剂极性的增加,其ICT(分子内电荷转移)发射显着红移。有趣的是,带有两个末端三苯胺基团的化合物QTPA2表现出可逆的机械荧光变色现象QTPA2的合成晶体的发射原子在542nm处定位,并且在研磨时它被红移至592nm,因此发射颜色从黄色变为胭脂红。同时,将磨碎的粉末用DCM蒸气熏蒸可回收排放物。XRD图谱和DSC曲线在不同的固态下表明,机械氟致变色是由于结晶态和非晶态之间的转变引起的。此外,TFA对合成的氨基苯乙烯基喹喔啉的质子化作用可能导致溶液的颜色从黄色变为深绿色,同时伴随着发射的猝灭。此外,我们还发现QTPA2的排放TFA蒸气可以显着地淬灭膜中的痕量汞,检测限和衰减时间估计分别为167 ppb和0.47 s。因此,氨基苯乙烯基喹喔啉衍生物可用作感官材料,以肉眼检测溶液和薄膜中的酸。

更新日期:2018-01-08
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