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Highly emissive, naked-eye solvatochromic probe based on styryl tetrahydrodibenzo[a,i]phenanthridine for acidochromic applications

机译:基于STYRYL四氢二苯甲苯的高发光,裸眼溶色溶解探针[A,I]苯吖啶用于抗性化学应用

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A new series of 5-styryl tetrahydrodibenzo[ a , i ]phenanthridines was readily synthesized from β-tetralone, ammonium acetate and cinnamaldehydes. These dyes emitted light with large Stokes shift values of 3894–7265 cm ~(?1) , depending on the nature of the substituent. The dyes displayed positive solvatochromism in their emission spectra, suggestive of a more polar excited state. Dye 3c exhibited aggregation-induced emission (AIE) property in 10% THF–water mixture besides a ratiometric response to pH from 10.75 to 2.16 with blue shift of 84 nm in emission. The emission ratio ( I _(526) ?:? I _(442) ) further displayed a good linearity with pH in the range of 4.1 to 6.8 and the corresponding p K _(a) value was found to be 4.55 ± 0.03. The addition of TFA led to a prominent bathochromic shift in spectra along with clear colour changes owing to protonation at the phenanthridine segment. Further, a second protonation of the phenanthrinium segment could take place based on the p K _(a) strength of the acid added. The pH dependent spectral changes were successfully applied to quantitatively detect pH in biological fluids and acid impurities in solvents.
机译:一种新的5-styryl四氢二苯并苯并[a,i]菲利番素易于从β-tetralone,醋酸铵和肉桂醛合成。根据取代基的性质,这些染料具有3894-7265cm〜(α1)的大小换档值。染料在其发射光谱中显示出阳性溶性溶解度,提示更极地激发态。除了对10%的THF-水混合物中,染料3C在10%THF-水混合物中表现出聚集诱导的发射(AIE)性能,除了10.75至2.16,发射中的84nm的蓝色移位。发射比(I _(526)?:ΔI_(442))进一步展示了4.1至6.8的pH的良好线性,并且发现相应的Pκ(a)值为4.55±0.03。 TFA的添加导致光谱中的突出的碱基转变,并且由于菲素段的质子化而显然的颜色变化。此外,菲蒽段的第二质子化可以基于添加的酸的Pκ_(a)强度进行。成功地应用pH依赖性光谱变化以在溶剂中定量地检测在生物流体和酸杂质中的pH。

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