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

Abstract

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.

Detection of Residual 2-Phenylphenol on Lemon Rind by Electrochemically Deposited Poly(hydroxybenzaldehyde) and Poly(hydroxybenzoic acid) Polymeric Stackings as Electrode Modifiers

“…As the outlined polymers are hydrophobic, they keep the aqueous solutions away from the electrode surface where they cover it as it was found in a recent work [23]. So there is a simple and fast method to decide whether coherent film forms at the electrode.…”

“…A cavitand bearing four 2-biphenyloxy moieties at the upper rim was used to the properties of the previously deposited phenolic compounds shown in the schem graph of the process (Figure 2). In a recent work this cavitand was copolymerized in sityl oxide with the phenylphenol isomers [23]. The co-deposited polymer in this A cavitand bearing four 2-biphenyloxy moieties at the upper rim was used to alter the properties of the previously deposited phenolic compounds shown in the schematic graph of the process (Figure 2).…”

“…The co-deposited polymer in this A cavitand bearing four 2-biphenyloxy moieties at the upper rim was used to alter the properties of the previously deposited phenolic compounds shown in the schematic graph of the process (Figure 2). In a recent work this cavitand was copolymerized in mesityl oxide with the phenylphenol isomers [23]. The co-deposited polymer in this way showed only a subtle improvement in increase of sensitivity compared with films deposited without this cavitand.…”

“…In fact, a copolymer will be the product of these reactions taking place in mesityl oxide due to the carbon-carbon double bond of solvent also when an electroactive substrate is present in solution. The polymers formed in mesityl oxide showed advantageous properties in electrochemical analysis compared with methyl isobutyl ketone possessing very similar chemical structure as in this solvent organic deposits formed predominantly with tortuosity governed properties [23].…”