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Syntheses and modifications of bisdiazonium salts of 3,8-benzo[c]cinnoline and 3,8-benzo[c]cinnoline 5-oxide onto glassy carbon electrode and the characterization of the modified surfaces

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Abstract

The goal of this study was to prepare novel glassy carbon electrode surfaces using two similar bis-diazonium salts, 3,8-benzo[c]cinnoline (3,8-BCC-BDAS) and 3,8-benzo[c]cinnoline 5-oxide (3,8-BCCNO-BDAS) at the glassy carbon (GC) surface. These diazonium salts were reduced electrochemically and covalently electrografted onto the glassy carbon electrode surface to form modified electrodes. Electrochemical reduction of 3,8-BCC-BDAS and 3,8-BCCNO-BDAS salts on the electrode surface yielded a compact and stable film. The existence of BCC moieties on the GC surface was characterized by X-ray photoelectron spectroscopy, reflectance-adsorption infrared spectroscopy, cyclic voltammetry, ellipsometry, and electrochemical impedance spectroscopy. The stability and working potential range of the novel modified electrodes were also studied. The possibility of analytical application of these novel surfaces for inorganic cations and especially selectivity to copper ions was investigated. 3,8-diaminobenzo[c]cinnoline (3,8-DABCC) and its 5-oxide derivative (3,8-DABCCNO) were synthesized from the reductive cyclization of 2,2′-dinitrobenzidine and prepared their bisdiazonium salts via the tetrazotization reactions of the diamines with NaNO2. The structures of 3,8-DABCC and 3,8-DABCCNO and their corresponding bisdiazonium salts are confirmed by spectral analysis.

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Acknowledgments

This work was supported by the Ankara University Scientific Research Fund with Project Grant numbers of 2000-07-05-019 and 2003-07-05-084 and by the TUBITAK (Scientific and Technological Research Council of Turkey) project with a number of 106T622.

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Authors and Affiliations

  1. Faculty of Science, Department of Chemistry, Ankara University, 06100, Tandogan, Ankara, Turkey

    Aybüke A. İsbir-Turan, Emine Kılıç, Haslet Ekşi, Ali Osman Solak & Betül Zorer

  2. Faculty of Art and Sciences, Department of Chemistry, Dumlupınar University, Kütahya, Turkey

    Zafer Üstündağ

  3. Faculty of Engineering, Department of Chemical Engineering, Kyrgyz-Turk Manas University, Bishkek, Kyrgyzstan

    Ali Osman Solak

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  1. Aybüke A. İsbir-Turan
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  2. Emine Kılıç
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Correspondence to Ali Osman Solak.

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İsbir-Turan, A.A., Kılıç, E., Üstündağ, Z. et al. Syntheses and modifications of bisdiazonium salts of 3,8-benzo[c]cinnoline and 3,8-benzo[c]cinnoline 5-oxide onto glassy carbon electrode and the characterization of the modified surfaces. J Solid State Electrochem 16, 235–245 (2012). https://doi.org/10.1007/s10008-011-1319-6

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  • DOI: https://doi.org/10.1007/s10008-011-1319-6

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