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A novel pyrazoline-based fluorescence probe armed by pyrene and naphthol system for the selective detection of Cu2+ and its biological application

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Abstract

A photo-induced electron transfer cationic fluorescence probe L1 based on pyrene-naphthol system was designed to detect the change of Cu2+ with fluorescence. The probe L1 was found to selectively recognize Cu2+ in aqueous ethanol solution [10.0 mmol/L HEPES, pH 7.4, EtOH–H2O = 1:1 (v/v)] without interference from other coexisting metal ions. The response of the sensor to Cu2+ is transient and reversible, and anions generally have no impact on the selectivity of Cu2+. Probe L1 forms complex with Cu2+ in 1:1 ratio as supported by Job’s plot analysis. The binding constants of Cu2+ was calculated to be 6.322 × 104 L/mol using a nonlinear curve-fitting method. The detection limit of Cu2+ was determined to be 1.620 × 10–7 mol/L. The energy gap between HOMO and LUMO in L1 and L1–Cu2+ was calculated by density functional theory as 3.76 eV and 2.71 eV, respectively. In addition, the probe L1 has extremely low cytotoxicity and can be used for living cell imaging studies.

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Authors and Affiliations

  1. School of Petrochemical Engineering, Lanzhou University of Technology, Lanzhou, 730050, China

    Yun-Shang Yang, Jing-Qi Cao, Chun-Mei Ma & Ying-Peng Zhang

  2. State Key Laboratory of Veterinary Etiological Biology and National Foot and Mouth Disease Reference Laboratory, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences, Lanzhou, 730046, China

    Hui-Chen Guo

  3. State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China

    Ji-Jun Xue

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  1. Yun-Shang Yang
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Correspondence to Yun-Shang Yang or Ying-Peng Zhang.

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Yang, YS., Cao, JQ., Ma, CM. et al. A novel pyrazoline-based fluorescence probe armed by pyrene and naphthol system for the selective detection of Cu2+ and its biological application. J IRAN CHEM SOC 19, 3451–3461 (2022). https://doi.org/10.1007/s13738-022-02536-5

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