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Spectroscopic study of cyclen-based 19F NMR probe for detection of hydrogen sulfide

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Abstract

A cyclen-based 19F NMR probe (F-cyclen) for hydrogen sulfide (H2S) has been prepared and evaluated for its complex formation ability with Cu2+ ions and responsivity to H2S. F-Cyclen was readily synthesized by reacting cyclen with 4-(trifluoromethyl)benzyl bromide. Visible absorption spectrophotometry showed that, same as the original cyclen, F-cyclen formed a 1:1 complex with Cu2+ ions. The 19F NMR signal of F-cyclen at 16.5 ppm gradually decreased in intensity with increasing CuCl2 concentration, with trifluoromethane sulfonic acid sodium salt (TFMSNa) used as an internal standard (0 ppm). When the Cu2+–F-cyclen complex was subjected to an increasing concentration of Na2S (as H2S donor), its corresponding 19F NMR signal of F-cyclen at 16.5 ppm gradually increased in intensity. The regression curve between the 19F NMR signal intensity ratio of F-cyclen to TFMSNa and Na2S concentration showed good linearity (r = 0.986) over the Na2S concentration range of 25–150 μM.

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Acknowledgements

We thank two undergraduate students, Mr. D. Yamamoto and Mr. Y. Hariki, for their experimental assistance. We also thank Simon Partridge, PhD, from Edanz (https://jp.edanz.com/ac) for editing a draft of this manuscript.

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Authors and Affiliations

  1. Department of Analytical Chemistry, Kyoto Pharmaceutical University, 5 Misasaginakauchi-cho, Yamashina-ku, Kyoto, 607-8414, Japan

    Shigehiko Takegami, Yuki Aramoto & Atsuko Konishi

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  1. Shigehiko Takegami
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  2. Yuki Aramoto
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  3. Atsuko Konishi
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Correspondence to Shigehiko Takegami.

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Takegami, S., Aramoto, Y. & Konishi, A. Spectroscopic study of cyclen-based 19F NMR probe for detection of hydrogen sulfide. ANAL. SCI. 38, 813–820 (2022). https://doi.org/10.1007/s44211-022-00100-y

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