An OFF–ON–OFF type fluorescent probe based on a naphthalene derivative for Al³⁺ and F⁻ ions and its biological application

Abstract

A novel fluorescent probe-based naphthalene Schiff, 1-(C2-glucosyl-ylimino-methyl)-naphthalene-2-ol (L) was synthesized by coupling d-glucosamine hydrochloride with 2-hydroxy-1-naphthaldehyde. It exhibited excellent selectivity and highly sensitivity for Al in ethanol with a strong fluorescence response, while other common metal ions such as Pb , Mg , Cu , Co , Ni , Cd , Fe , Mn , Hg , Li , Na , K , Fe , Cr , Zn , Ag , Ba and Ca did not cause the same fluorescence response. The probe selectively bound Al with a binding constant (K ) of 5.748 × 10 M and a lowest detection limit (LOD) of 4.08 nM. Moreover, the study found that the fluorescence of the L - Al complex could be quenched after addition of F in the same medium, while other anions, including Cl , Br , I , NO , NO , ClO , CO , HCO , SO , HSO , CH COO , PO , HPO , S and S O had nearly no influence on probe behaviour. Binding of the [L - Al ] complex to a F anion was established by different fluorescence titration studies, with a detection limit of 3.2 nM in ethanol. The fluorescent probe was also successfully applied in the imaging detection of Al and F in living cells.

The detection of multiple analytes by using visual colorimetric and fluorometric multimodal chemosensor based on the azo dye

“…The coordinate interaction between fluoride ions and hard metal ions is strong according to hard and soft acid base theory (such as [FeF 6 ] 3- and [AlF 6 ] 3- ), and it has been proved that the interactions between hard metal ions and F − would break the metal-ligand coordination bond [ 33 ]. To study the binding properties of “M n+ -MP ” (M n+ = Fe 3+ , Al 3+ ) with F ¯ , UV/Vis spectra titration was performed (Figures 6 and 7 ).…”

A Significant Fluorescence Turn-On Probe for the Recognition of Al3+ and Its Application

“…Enlightened by our previous work, a novel Schiff base fluorescent probe (E)-4-(benzo[d]thiazol-2-yl)-2-(((2-hydroxyphenyl)imino)methyl)-6-methoxyphenol (BHMMP) was easily synthesized and systematically investigated (Scheme 1), presenting a turn-on fluorescent response towards Al 3+ , which was ascribed to the inhibition of C=N isomerization and photo-induced electron transfer (PET) processes. A comparison of the probe BHMMP with the ones with the similar group was provided in Table S1 [45][46][47][48][49][50][51]. The unique advantages of BHMMP showed high sensitivity, good water solubility, significant recognition signal, and excellent potential application capabilities.…”

Investigating the Influence of Electronic Effects of Functional Groups on the Fluorescence Mechanism of Probes in Water Samples

“…Both Naph3 and its reaction product with formaldehyde (Naph3-S) do not produce fluorescence. Various fluorescent probes based on naphthalene derivatives have been designed, − but a distinct explanation for the quenching mechanism has not been provided. Thus, it is crucial to study the quenching mechanisms of fluorescent probes based on naphthalene derivatives.…”