Fluorogenic and chromogenic detection of biologically important fluoride anion in aqueous media with a fluorescein-linked hydrogen-bonding receptor via “off–on” approach

Abstract

A new kind of fluorescein-based chemosensor L toward anions was designed and synthesized. The chemosensor L could selectively sense F -and AcO -among test anions, which was accompanied by the ''off-on'' fluorescence enhancement and ''colorless-to-yellow'' color changes. The anion bonding ability of L was checked by UV-vis, FL, and 1 HNMR titration experiments. Notably, the compound L could detect F -in 30 % aqueous solution (DMSO: Water = 7:3, v: v) with 0.36 ppm sensitivity through selectively fluorescence enhancement by cooperative interaction of ''ring-open'' reaction and hydrogen bonding.

Green and Red Fluorescent Dyes for Translational Applications in Imaging and Sensing Analytes: A Dual‐Color Flag

“…Several fluorescein derivatives for fluoride detection have been synthesized; however, these probes do not selectively detect fluoride, as they suffer from interference from other anions. Asthana and co‐workers report the synthesis of fluoride‐selective “turn‐on” fluorescein probe 41 containing nitrobenzenesulfonyl chloride as a masking unit (see Figure ).…”

The Exception That Proves the Rule: How Sodium Chelation Can Alter the Charge‐Cell Binding Correlation of Fluorescein‐Based Multimodal Imaging Agents

“…This apparently aberrant behavior is explainable assuming a previously undescribed mechanism of chelation of sodium ions by fluorescein. Interactions of fluorescein derivatives with metal ions have been reported in literature and exploited for their application as fluorescent chemosensors for the detection of both cations and anions [19–22] . The binding mode proposed in this work consists of an interaction between the phenolic and the carboxylic group of fluorescein and one sodium ion (Figure 4A).…”

“…Interactions of fluorescein derivatives with metal ions have been reported in literature and exploited for their application as fluorescent chemosensors for the detection of both cations and anions. [19][20][21][22] The binding mode proposed in this work consists of an interaction between the phenolic and the carboxylic group of fluorescein and one sodium ion (Figure 4A). As a result, the introduction of a positively charged metal ion in the predicted proteolytic conformation of the fluorescein moiety can entail a masking of one anionic group and a reduction of the total net charge of compound 1 a, explaining its unexpected GRPR binding behavior.…”

Fluorogenic and chromogenic detection of biologically important fluoride anion with schiff-bases containing 4-amino-1,8-naphthalimide unit

“…Moreover, the Hs of phenyl group showed no changes, which also indicated the strong hydrogen-bonding interactions rather than deprotonation process between L2 and fluoride anions (Fig. 9b) [7]. From the above results, the selectivity of L1 over L2 toward F À could be explained by the following reason: the electron withdrawing effect of anions and planarity of the resulting complex were the main factors for the fluorescence quenching of L1.…”

“…Three kinds of signals such as optical, electrochemical, and mass signals are extensively used to study the anion recognition events. Among them, colorimetric and fluorescent sensors are especially attractive, since they allow the so called "naked-eye" detection, and they are qualified with fast response, high selectivity as well as inexpensive installations [6,7]. Especially, the probes possessing optical signals in NIR region are of great interest owing to its merit of avoiding interference from endogenous chromophores in biological system [8][9][10].…”