Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media
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 electrooxi...
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2022-08-01
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| author | László Kiss Zoltán Nagymihály Péter Szabó László Kollár Sándor Kunsági-Máté |
| author_facet | László Kiss Zoltán Nagymihály Péter Szabó László Kollár Sándor Kunsági-Máté |
| author_sort | László Kiss |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T01:31:40Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T01:31:40Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-6f6874b3a68844508b10bced87aaf49c2023-11-23T13:40:46ZengMDPI AGMolecules1420-30492022-08-012717536610.3390/molecules27175366Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic MediaLászló Kiss0Zoltán Nagymihály1Péter Szabó2László Kollár3Sándor Kunsági-Máté4Department of Organic and Medicinal Chemistry, University of Pécs, Honvéd Street 1, H 7624 Pécs, HungaryJános Szentágothai Research Center, Ifjúság útja 20, H 7624 Pécs, HungaryEnvironmental Analytical and Geoanalytical Research Group, Szentágothai Research Center, Ifjúság útja 20, H 7624 Pécs, HungaryJános Szentágothai Research Center, Ifjúság útja 20, H 7624 Pécs, HungaryDepartment of Organic and Medicinal Chemistry, University of Pécs, Honvéd Street 1, H 7624 Pécs, HungaryThe 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.https://www.mdpi.com/1420-3049/27/17/5366phenylphenolsmethyl isobutyl ketonemesityl oxidecavitand |
| spellingShingle | László Kiss Zoltán Nagymihály Péter Szabó László Kollár Sándor Kunsági-Máté Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media Molecules phenylphenols methyl isobutyl ketone mesityl oxide cavitand |
| title | Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media |
| title_full | Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media |
| title_fullStr | Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media |
| title_full_unstemmed | Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media |
| title_short | Anodic Polymerization of Phenylphenols in Methyl Isobutyl Ketone and Mesityl Oxide: Incorporation of a Cavitand into the Layers Formed for Sensing Phenols in Organic Media |
| title_sort | anodic polymerization of phenylphenols in methyl isobutyl ketone and mesityl oxide incorporation of a cavitand into the layers formed for sensing phenols in organic media |
| topic | phenylphenols methyl isobutyl ketone mesityl oxide cavitand |
| url | https://www.mdpi.com/1420-3049/27/17/5366 |
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