Pyrene-Based Fluorescent Probe for “Off-on-Off” Sequential Detection of Cu2+ and CN with HeLa Cells Imaging

Muthaiah Shellaiah, Parthiban Venkatesan, Natesan Thirumalaivasan*, Shu Pao Wu*, Kien Wen Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations


The novel pyrene-appended Schiff base probe L with aggregation-induced emissions (AIE) relevant to an increase in water fractions (0–90%) is synthesized and applied in sequentially detecting Cu2+ and CN. The pyrene-based probe L firstly induces the excimer formation in the presence of Cu2+. However, the process can be reversed by sequentially adding CN, which is demonstrated using the fluorescence “Off-On-Off” response in semi-aqueous media ethanol water (v/v = 7/3) under physiological pH (5 mM HEPES, pH 7.0). The Job’s plot, mass analysis, 1H NMR titrations, and density functional theory (DFT) interrogations confirm the 2:1 stoichiometry of excimer complex L–Cu2+-L*, preferential binding atoms, and CN tuned complex reversibility. Based on the photoluminescence (PL) titration, the association constant of L to Cu2+ is determined as 4.95 × 106 M−1. From standard deviation and linear fittings, the detection limits (LODs) of Cu2+ and CN are estimated as 219 nM and 580 nM, respectively. The practicality of Cu2+ and CN detection is demonstrated using a TLC plate and a blended polymer membrane through which significant color changes under a UV lamp can be monitored. Moreover, utility of the designed probe L towards biological application with low toxicity is demonstrated by detecting Cu2+ and CN inside HeLa cells. The responses of the probe to Cu(II) ions were also verified using living HeLa cells imaging.

Original languageEnglish
Article number115
Issue number2
StatePublished - Feb 2023


  • aggregation-induced emissions
  • biocompatibility
  • cell imaging
  • chemosensor
  • copper ion
  • cyanide ion
  • polymer membrane sensor
  • pyrene derivative sequential detection


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