Department of Organic and Medicinal Chemistry, University of Pécs, Honvéd Street 1, H 7624 Pécs, Hungary.
János Szentágothai Research Center, Ifjúság útja 20, H 7624 Pécs, Hungary.
Molecules. 2022 Aug 23;27(17):5366. doi: 10.3390/molecules27175366.
The electropolymerization of three phenylphenol isomers was studied in methyl isobutyl ketone and mesityl oxide, and the remarkable differences highlighted the importance of the carbon-carbon double bond in mesityl oxide. In the case of each substrate, a brownish deposit formed during the electrooxidation. The obvious difference between the polymers formed from the two solvents was recognized via voltammetric signal enhancement of 4-methoxyphenol and 4-chlorophenol, and it was only observed in the case of mesityl oxide. The experiments highlighted that incorporation of a cavitand with biphenyl groups on the upper rim of the polymers of phenylphenols improved the results to a small extent. The cavitand was, itself, electroactive without any fouling effect. As 2-phenylphenol is by far the cheapest of the three isomers, a cavitand was incorporated into its polymer, which was exploited to solve analytical problems while mesityl oxide was used as solvent. Useful quantifications were achieved in organic solvents; however, it failed under aqueous conditions due to the high hydrophobicity of the deposit. Application of differential pulse voltammetry for 4-methoxyphenol and 4-chlorophenol gave detection limits of 9.28 and 50.8 μM in acetonitrile, respectively. This procedure resulted in the immobilization of cavitand derivatives onto the electrode's surface, and the layer formed offered selective sensing of phenols by electrochemical methods.
三种苯二酚异构体在甲基异丁基酮和均三甲氧基苯中的电化学聚合进行了研究，碳-碳双键在均三甲氧基苯中的重要性得到了显著体现。在每种底物的情况下，电氧化过程中都会形成棕褐色沉积物。通过对 4-甲氧基苯酚和 4-氯苯酚的伏安信号增强，发现了两种溶剂形成的聚合物之间的明显差异，而这种差异仅在均三甲氧基苯中观察到。实验表明，在苯二酚聚合物的上边缘引入具有联苯基团的杯芳烃，在一定程度上改善了结果。杯芳烃本身没有任何污垢效应，具有电化学活性。由于三种异构体中 2-苯二酚是最便宜的，因此将杯芳烃引入其聚合物中，利用均三甲氧基苯作为溶剂来解决分析问题。在有机溶剂中实现了有用的定量，但由于沉积物的高疏水性，在水相条件下失败。差分脉冲伏安法用于 4-甲氧基苯酚和 4-氯苯酚的检测限分别为 9.28 和 50.8 μM，在乙腈中。该程序导致杯芳烃衍生物固定在电极表面，形成的层通过电化学方法提供了对酚类物质的选择性传感。
