Construction of anthraquinone functional zinc phthalocyanine sensor platform for ultra-trace amount of water determination in tetrahydrofuran and N,N-Dimethylformamide

Mustafa Semih Yildirim; Yusuf Alcay; Ozgur Yavuz; Secil Kirlangic Atasen; Zeliha Mermer; Hulya Aribuga; Ismail Yilmaz

doi:10.1016/j.aca.2022.339531

Construction of anthraquinone functional zinc phthalocyanine sensor platform for ultra-trace amount of water determination in tetrahydrofuran and N,N-Dimethylformamide

Mustafa Semih Yildirim, Yusuf Alcay, Ozgur Yavuz, Secil Kirlangic Atasen, Zeliha Mermer, Hulya Aribuga, Ismail Yilmaz^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Anthraquinone functional zinc phthalocyanine sensor platform was utilized for ultra-trace amount of water determination in THF and DMF. Using the fluorometric method, the water content in THF was determined with a LOD of 2.27 × 10⁻⁴ M and a response time of 1 s. The sensor is based on the mechanism of aggregation depended on quenching of emission. Although the aggregation is known as an undesirable property in the application of phthalocyanine, this property has been successfully applied in the quantification of water content in THF. By using the shift of the third reduction wave of the sensor, the water content in DMF was measured with a LOD value of 5.64 × 10⁻⁷ M. The voltammetric response mechanism is based on the hydrogen bonding depended shifting of the reduction potential of quinone moiety on phthalocyanine. Redox potentials of phthalocyanine are used as a calibrant for accurate quantification of water content in DMF. Water molecules (n and m) and equilibrium constants (K¹ and K²) for the formation of hydrogen bonding for the first and third reduction processes were calculated as 1.18 (n), 10.4 (m) and 19.3 (K¹), 1.6 × 10¹¹ (K²) M^−(m-n), which demonstrated why the third reduction process was chosen to set the calibration plots.

Original language	English
Article number	339531
Journal	Analytica Chimica Acta
Volume	1198
DOIs	https://doi.org/10.1016/j.aca.2022.339531
Publication status	Published - 15 Mar 2022

Bibliographical note

Publisher Copyright:
© 2022 Elsevier B.V.

Funding

When the voltammogram belonging to (AQ)4-ZnPc is examined to elucidate the electron transfer mechanism, it is understood that the current of the anodic peak corresponding to the third reduction wave is smaller than that of the first reduction wave (Fig. 7b). The current loss is likely due to the complexation of the neutral form of (AQ)4-ZnPc with the third-reduced product (AQ2−)4-ZnPc− or the adsorption of the third reduced products to the surface of the electrode. Our previous study on the ferrocene-derived naphthoquinone supports this situation [28]. Scheme 1 represents the mechanism of the electron transfer reaction of (AQ)4-ZnPc in the absence and presence of water in DMF in the electrochemical cell. In Scheme 1, the reversible interactions between sensor (AQ)4-ZnPc and water molecules are illustrated through the anion radical and polyanion type of each anthraquinone unit of the Pc.We would like to thank Istanbul Technical University for support.

Funders	Funder number
Istanbul Teknik Üniversitesi

Keywords

Anthraquinone
Electrochemistry
Fluorescence
Phthalocyanine
Water sensor

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title = "Construction of anthraquinone functional zinc phthalocyanine sensor platform for ultra-trace amount of water determination in tetrahydrofuran and N,N-Dimethylformamide",

abstract = "Anthraquinone functional zinc phthalocyanine sensor platform was utilized for ultra-trace amount of water determination in THF and DMF. Using the fluorometric method, the water content in THF was determined with a LOD of 2.27 × 10−4 M and a response time of 1 s. The sensor is based on the mechanism of aggregation depended on quenching of emission. Although the aggregation is known as an undesirable property in the application of phthalocyanine, this property has been successfully applied in the quantification of water content in THF. By using the shift of the third reduction wave of the sensor, the water content in DMF was measured with a LOD value of 5.64 × 10−7 M. The voltammetric response mechanism is based on the hydrogen bonding depended shifting of the reduction potential of quinone moiety on phthalocyanine. Redox potentials of phthalocyanine are used as a calibrant for accurate quantification of water content in DMF. Water molecules (n and m) and equilibrium constants (K1 and K2) for the formation of hydrogen bonding for the first and third reduction processes were calculated as 1.18 (n), 10.4 (m) and 19.3 (K1), 1.6 × 1011 (K2) M−(m-n), which demonstrated why the third reduction process was chosen to set the calibration plots.",

keywords = "Anthraquinone, Electrochemistry, Fluorescence, Phthalocyanine, Water sensor",

author = "Yildirim, {Mustafa Semih} and Yusuf Alcay and Ozgur Yavuz and Atasen, {Secil Kirlangic} and Zeliha Mermer and Hulya Aribuga and Ismail Yilmaz",

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AU - Alcay, Yusuf

AU - Yavuz, Ozgur

AU - Atasen, Secil Kirlangic

AU - Mermer, Zeliha

AU - Aribuga, Hulya

AU - Yilmaz, Ismail

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KW - Anthraquinone

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Construction of anthraquinone functional zinc phthalocyanine sensor platform for ultra-trace amount of water determination in tetrahydrofuran and N,N-Dimethylformamide

Abstract

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Keywords

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