首页> 外文期刊>The Journal of Organic Chemistry >Nitro-Substituted 4?[(Phenylmethylene)imino]phenolates: Solvatochromism and Their Use as Solvatochromic Switches and as Probes for the Investigation of Preferential Solvation in Solvent Mixtures
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Nitro-Substituted 4?[(Phenylmethylene)imino]phenolates: Solvatochromism and Their Use as Solvatochromic Switches and as Probes for the Investigation of Preferential Solvation in Solvent Mixtures

机译:硝基取代的4?[((苯基亚甲基)亚氨基]酚盐:溶剂致变色及其在溶剂致变色开关中的应用以及用于研究溶剂混合物中优先溶剂化的探针

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Four 4-[[(4-nitrophenyl)methylene]imino]phenols (2a−d) were synthesized. After deprotonation in solution,nthey formed the solvatochromic phenolates 3a−d, which revealed a reversal in solvatochromism. Their UV−vis spectroscopicnbehavior was explained on the basis of the interaction of the dyes with the medium through combined effects, such as nonspecificnsolute−solvent interactions and hydrogen bonding between the solvents and the nitro and phenolate groups. Dyes 3a−c werenused as probes to investigate binary solvent mixtures, and the synergistic behavior observed was attributed to solvent−solventnand solute−solvent interactions. A very unusual UV−vis spectroscopic behavior occurred with dye 3d, which has in its molecularnstructure two nitro substituents as acceptor groups and two phenyl groups on the phenolate moiety. In alcohol/water mixtures,nthe ET(3d) values increase from pure alcohol (methanol, ethanol, and propan-2-ol) until the addition of up to 80−96% water.nSubsequently, the addition of a small amount of water causes a very sharp reduction in the ET(3d) value (for methanol, thisncorresponds to a bathochromic shift from 543 to 732 nm). This represents the first example of a solvatochromic switch triggerednby a subtle change in the polarity of the medium, the color of the solutions being easily reversed by adding small amounts of thenrequired cosolvent.
机译:合成了四个4-[[((4-硝基苯基)亚甲基]亚氨基]苯酚(2a-d)。在溶液中去质子化之后,它们形成溶剂变色酚盐3a-d,这揭示了溶剂变色现象的逆转。通过结合效应,如非特异性溶质-溶剂相互作用以及溶剂与硝基和酚盐基团之间的氢键结合作用,说明了染料与介质的相互作用,解释了它们的紫外可见光谱行为。染料3a-c被用作研究二元溶剂混合物的探针,观察到的协同行为归因于溶剂-溶剂和溶质-溶剂的相互作用。染料3d发生了非常不寻常的UV-vis光谱行为,染料3d的分子结构中有两个硝基取代基作为受体基团,在酚盐部分上具有两个苯基基团。在酒精/水混合物中,从纯酒精(甲醇,乙醇和丙-2-醇)开始直到添加最多80-96%的水为止,其ET(3d)值会增加.n随后添加少量的水导致ET(3d)值急剧下降(对于甲醇,这对应于从543 nm到732 nm的红移)。这代表了溶剂变色开关的第一个例子,该变色开关是由介质极性的细微变化触发的,溶液的颜色很容易通过添加少量然后需要的助溶剂来逆转。

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