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Synthesis and fluorescence properties of a 1,3-disubstituted thiacalix[4]arene crown-5 armed with phenothiazine moieties

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Abstract

A new thiacalix[4]arene phenothiazine derivative (2) based on a thiacalix[4]crown with a 1,3-alternate conformation has been synthesized and characterized. In THF-water mixture, Compound 2 exhibits a strong fluorescence emission, with a large Stokes shift (λex/em = 357 nm/505 nm, Δλ = 148 nm), which helps to avoid interference in excitation and emission. For the metal ions tested, the fluorescence of Compound 2 was quenched only by Fe3+ and Cr3+ ions. Evidence for the hydrolysis reaction promoted by the metal ions is given by X-ray crystallography, mass spectra (MS), infrared (IR) spectra, and fluorescence spectroscopy data.

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Authors and Affiliations

  1. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, 550025, China

    Qiang Sun, Lan Mu & Xi Zeng

  2. Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga, 840-8502, Japan

    JiangLin Zhao & Takehiko Yamato

  3. The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang, 550002, China

    JianXin Zhang

Authors
  1. Qiang Sun
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  2. Lan Mu
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  3. Xi Zeng
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  4. JiangLin Zhao
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  5. Takehiko Yamato
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  6. JianXin Zhang
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Correspondence to Xi Zeng or Takehiko Yamato.

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Sun, Q., Mu, L., Zeng, X. et al. Synthesis and fluorescence properties of a 1,3-disubstituted thiacalix[4]arene crown-5 armed with phenothiazine moieties. Sci. China Chem. 58, 539–544 (2015). https://doi.org/10.1007/s11426-014-5202-z

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  • DOI: https://doi.org/10.1007/s11426-014-5202-z

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