Synthesis of Novel One-Walled meso-Phenylboronic Acid-Functionalized Calix[4]pyrrole: A Highly Sensitive Electrochemical Sensor for Dopamine

Facile access to new one-walled meso-substituted phenylboronic acid-functionalized calix[4]­pyrrole (C4P) has been revealed for the first time, starting from cost-effective and easily accessible materials. The structures of both the intermediate dipyrromethane (DPM) and the targeted functionalized C...

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Published inACS omega Vol. 7; no. 17; pp. 15082 - 15089
Main Authors Rather, Ishfaq Ahmad, Sofi, Feroz Ahmad, Bhat, Mohsin Ahmad, Ali, Rashid
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 03.05.2022
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Abstract Facile access to new one-walled meso-substituted phenylboronic acid-functionalized calix[4]­pyrrole (C4P) has been revealed for the first time, starting from cost-effective and easily accessible materials. The structures of both the intermediate dipyrromethane (DPM) and the targeted functionalized C4P have been confirmed by means of 1H-NMR, 13C-NMR, IR, and HRMS spectral data. The voltammetric investigations of the functionalized C4P films cast over a glassy carbon electrode (C4P-GCE) clearly establish the redox stability and redox accessibility of the boronic acid functional moiety present in the C4P framework. We demonstrate that the presence of the unique boronic acid functionality in the C4P endows it with an excellent potential for the highly sensitive electrochemical sensing of the neurotransmitter dopamine (DA). A linear correlation between the strength of the Faradaic signals corresponding to the electro-oxidation of DA over C4P-GCE and the concentration of DA was observed in a concentration range as wide as 0.165–2.302 μM. The C4P-GCE has revealed exceptional stability and reproducibility in the electrochemical sensing of DA, with a nanomolar level limit of detection as low as 15 nM.
AbstractList Facile access to new one-walled -substituted phenylboronic acid-functionalized calix[4]pyrrole (C4P) has been revealed for the first time, starting from cost-effective and easily accessible materials. The structures of both the intermediate dipyrromethane (DPM) and the targeted functionalized C4P have been confirmed by means of H-NMR, C-NMR, IR, and HRMS spectral data. The voltammetric investigations of the functionalized C4P films cast over a glassy carbon electrode (C4P-GCE) clearly establish the redox stability and redox accessibility of the boronic acid functional moiety present in the C4P framework. We demonstrate that the presence of the unique boronic acid functionality in the C4P endows it with an excellent potential for the highly sensitive electrochemical sensing of the neurotransmitter dopamine (DA). A linear correlation between the strength of the Faradaic signals corresponding to the electro-oxidation of DA over C4P-GCE and the concentration of DA was observed in a concentration range as wide as 0.165-2.302 μM. The C4P-GCE has revealed exceptional stability and reproducibility in the electrochemical sensing of DA, with a nanomolar level limit of detection as low as 15 nM.
Facile access to new one-walled meso -substituted phenylboronic acid-functionalized calix[4]pyrrole (C4P) has been revealed for the first time, starting from cost-effective and easily accessible materials. The structures of both the intermediate dipyrromethane (DPM) and the targeted functionalized C4P have been confirmed by means of 1 H-NMR, 13 C-NMR, IR, and HRMS spectral data. The voltammetric investigations of the functionalized C4P films cast over a glassy carbon electrode (C4P-GCE) clearly establish the redox stability and redox accessibility of the boronic acid functional moiety present in the C4P framework. We demonstrate that the presence of the unique boronic acid functionality in the C4P endows it with an excellent potential for the highly sensitive electrochemical sensing of the neurotransmitter dopamine (DA). A linear correlation between the strength of the Faradaic signals corresponding to the electro-oxidation of DA over C4P-GCE and the concentration of DA was observed in a concentration range as wide as 0.165–2.302 μM. The C4P-GCE has revealed exceptional stability and reproducibility in the electrochemical sensing of DA, with a nanomolar level limit of detection as low as 15 nM.
Facile access to new one-walled meso-substituted phenylboronic acid-functionalized calix[4]­pyrrole (C4P) has been revealed for the first time, starting from cost-effective and easily accessible materials. The structures of both the intermediate dipyrromethane (DPM) and the targeted functionalized C4P have been confirmed by means of 1H-NMR, 13C-NMR, IR, and HRMS spectral data. The voltammetric investigations of the functionalized C4P films cast over a glassy carbon electrode (C4P-GCE) clearly establish the redox stability and redox accessibility of the boronic acid functional moiety present in the C4P framework. We demonstrate that the presence of the unique boronic acid functionality in the C4P endows it with an excellent potential for the highly sensitive electrochemical sensing of the neurotransmitter dopamine (DA). A linear correlation between the strength of the Faradaic signals corresponding to the electro-oxidation of DA over C4P-GCE and the concentration of DA was observed in a concentration range as wide as 0.165–2.302 μM. The C4P-GCE has revealed exceptional stability and reproducibility in the electrochemical sensing of DA, with a nanomolar level limit of detection as low as 15 nM.
Author Rather, Ishfaq Ahmad
Sofi, Feroz Ahmad
Ali, Rashid
Bhat, Mohsin Ahmad
AuthorAffiliation Department of Chemistry
Organic and Supramolecular Functional Materials Research Laboratory, Department of Chemistry
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Snippet Facile access to new one-walled meso-substituted phenylboronic acid-functionalized calix[4]­pyrrole (C4P) has been revealed for the first time, starting from...
Facile access to new one-walled -substituted phenylboronic acid-functionalized calix[4]pyrrole (C4P) has been revealed for the first time, starting from...
Facile access to new one-walled meso -substituted phenylboronic acid-functionalized calix[4]pyrrole (C4P) has been revealed for the first time, starting from...
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Title Synthesis of Novel One-Walled meso-Phenylboronic Acid-Functionalized Calix[4]pyrrole: A Highly Sensitive Electrochemical Sensor for Dopamine
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