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Synthesis of 3-Iodoindoles and Their Glucose Electrooxidation Performance as an Anode Catalyst

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Abstract

Herein, indole derivatives namely 3-iodo-1-methyl-2-phenyl-1H-indole (4A), 3-iodo-1-methyl-2-(p-tolyl)-1H-indole (4B), and 2-(2,5-dimethylphenyl)-3-iodo-1-methyl-1H-indole (4C) prepared by Sonogashira coupling and electrophilic cyclization reactions with yield of 70%, 68%, and 67%, respectively. Organic catalysts were characterized by using Liquid Chromatography with tandem mass spectrometry (LC–MS–MS), Transmission Electron Microscopy (TEM), Fourier Transform Infrared Spektrofotometre (FT-IR), and Nuclear Magnetic Resonance (NMR). Cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), and chronoamperometry (CA) were utilized to observe the electrocatalytic behavior of 4A, 4B, and 4C. Specific activity for glucose electrooxidation of 4A was determined as 3.26 mA/cm2. Compound 4A exhibits long-term stability toward glucose electrooxidation. As a metal-free catalyst, Compound 4A may be a good candidate as an electrocatalyst for glucose electrooxidation.

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Data Availability

All data, models, and code generated or used during the study appear in the submitted article.

Abbreviations

LC–MS/MS:

Liquid chromatography with tandem mass spectrometry

FT-IR:

Fourier transform infrared spectroscopy

NMR:

Nuclear magnetic resonance

CV:

Cyclic voltammetry

EIS:

Electrochemical impedance spectroscopy

CA:

Chronoamperometry

DGFC:

Direct glucose fuel cell

PdCl2(PPh3)2 :

Bis(triphenylphosphine)palladium(II) dichloride

Et3N:

Triethylamine

THF:

Tetrahydrofuran

CuI:

Copper(I) iodide

MgSO4 :

Magnesium sulfate

I2 :

Iodine

TLC:

Thin-layer chromatography

KOH:

Potassium hydroxide

RT:

Room temperature

J :

Coupling constant

δ:

Chemical shift in parts per million

CDCl3 :

Deuterochloroform

µL:

Microliter

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Acknowledgements

We acknowledge with gratitude the support provided by the TUBİTAK (120Z928) for chemicals.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Sciences, Van Yuzuncu Yil University, 65080, Van, Turkey

    Hatice Calis

  2. Department of Chemical Engineering, Faculty of Engineering, Van Yuzuncu Yil University, 65000, Van, Turkey

    Berdan Ulas & Yonca Yilmaz

  3. Department of Chemical Engineering, Faculty of Engineering and Architectural Sciences, Eskisehir Osmangazi University, 26040, Eskisehir, Turkey

    Hilal Kivrak & Emrah Kavak

  4. Translational Medicine Research and Clinical Center, Eskisehir Osmangazi University, 26040, Eskisehir, Turkey

    Hilal Kivrak

  5. Department of Chemistry, Faculty of Sciences, Eskişehir Osmangazi University, 26040, Eskisehir, Turkey

    Arif Kivrak

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  1. Hatice Calis
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Calis, H., Ulas, B., Yilmaz, Y. et al. Synthesis of 3-Iodoindoles and Their Glucose Electrooxidation Performance as an Anode Catalyst. Waste Biomass Valor 14, 3285–3295 (2023). https://doi.org/10.1007/s12649-023-02163-y

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