Abstract
The fluorescent sensor (3) based on the 1,3-alternate conformation of the thiacalix[4]arene bearing the coumarin fluorophore, appended via an imino group, has been synthesised. Sensing properties were evaluated in terms of a colorimetric and fluorescence sensor for Zn2+ and F−. High selectivity and excellent sensitivity were exhibited, and ‘off-on’ optical behaviour in different media was observed. All changes were visible to the naked eye, whilst the presence of the Zn2+ and F− induces fluorescence enhancement and the formation of a 1:1 complex with 3. In addition, 3 exhibits low cytotoxicity and good cell permeability and can readily be employed for assessing the change of intracellular levels of Zn2+ and F−.
Highlights
Cations and anions are ubiquitous in nature and play critical roles in many biological, chemical and environmental systems, for example zinc ions are indispensable metal ions in living systems
Upon the addition of F, Cl, Br, I, HSO4, AcO, NO3, ClO4, PF6- and H2PO4- anions to an CH3CN solution of 3, no significant spectral changes were observed in the UV-vis absorption spectra apart from in the case of the F- ion (Fig. 4)
The results indicated that no significant variation was found in the absorbance with or without the other anions present, the sensing of F- by the sensor was hardly affected by the previously listed anions (Fig. S9)
Summary
Cations and anions are ubiquitous in nature and play critical roles in many biological, chemical and environmental systems, for example zinc ions are indispensable metal ions in living systems. When Zn2+ was added to the solution of 3, a dramatic fluorescent enhancement was observed, suggesting that 3 showed a specific response to Zn2+ ions (Fig. 2A).
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