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Synthesis of a tetrapyrazinoporphyrazine-based fluorescent sensor for detection of Cu2+ ion

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Abstract

In this study, a novel tetrapyrazinoporphyrazine-based fluorescent sensor for Cu2+ ion was synthesized and fully characterized by 1H NMR, MALDI-TOF MS, and elemental analysis. A tetrapyrazinoporphyrazine substituent was used as the reporting group and a 2,2′-dipyridylamine moiety was employed as the recognition group. The effects of various metal ions on the absorption and emission spectra of the designed molecule were investigated, demonstrating that this compound shows selectivity and sensitivity toward the Cu2+ ion. Upon addition of Cu2+ ion, a fluorescent intensity of the tetrapyrazinoporphyrazine-based sensor decreased gradually at 655 nm. To confirm a selective binding ability of 2,2′-dipyridylamine moiety toward Cu2+ ion, a comparative study was performed using tetrapyrazinoporphyrazine derivative with bromine instead of 2,2′-dipyridylamine moiety. Furthermore, association constant and detection limit value of the synthesized compound toward Cu2+ ion were derived from a repetitive titration experiment. Also, a reversibility of the prepared sensor was confirmed through additional test using compound and ethylenediaminetetraacetic acid.

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Acknowledgements

This work was supported by the Technology Innovation Program (No. 10047756, Development of tetra-pyrrole type for Color, light-emitting, detecting Devices) funded by the Ministry of Trade, Industry & Energy (MI, Korea).

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Authors and Affiliations

  1. Department of Organic and Nano Engineering, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul, 133-791, South Korea

    Chang Young Jung, Wang Yao, Jong Min Park, Joong Hyun Cho, Dae Hyun Kim & Jae Yun Jaung

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  1. Chang Young Jung
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  2. Wang Yao
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  3. Jong Min Park
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  4. Joong Hyun Cho
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  5. Dae Hyun Kim
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Correspondence to Jae Yun Jaung.

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Jung, C.Y., Yao, W., Park, J.M. et al. Synthesis of a tetrapyrazinoporphyrazine-based fluorescent sensor for detection of Cu2+ ion. J Incl Phenom Macrocycl Chem 89, 85–90 (2017). https://doi.org/10.1007/s10847-017-0735-3

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  • DOI: https://doi.org/10.1007/s10847-017-0735-3

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