Pyrene Based Chemosensor for Selective Sensing of Fluoride in Aprotic and Protic Environment

Abstract

A new aromatic hydrazone based on pyrene-1-aldehyde was synthesized and characterized by (1)H NMR and mass spectrometric analyses. The sensing properties of the hydrazone were studied by absorption and fluorescence studies in the aprotic solvent DMSO. It was capable of visual and fluorescent detection of fluoride over competitive ions (Cl(-), Br(-), H2PO4 (-), AcO(-)). Moreover, the in-situ prepared iron(III) complex of the hydrazone was investigated as a turn off fluorescent fluoride sensor in aqueous medium by displacement mechanism.

BODIPY-Pyridylhydrazone Probe for Fluorescence Turn-On Detection of Fe3+ and Its Bioimaging Application

“…As displayed in Figure 7, the hydrazone proton signal (H4) at 8.06 ppm completely disappeared and the amine proton resonance (H5) at 10.98 ppm almost completely disappeared upon the addition of Fe 3+ . The rest of the proton peaks of pyridylhydrazone moiety became broader indicating that Fe 3+ bound to the PH unit which is consistent with the previous findings [25,53,54]. In addition, the detections of molecular ions at m/z = 639.0923 {[(BODIPY-PH-H)Fe(NO3)(DMSO)] + } and 684.0762 {[(BODIPY-PH-H)Fe(NO3)(DMSO)(EtOH)] from electrospray ionization mass spectra (ESI-MS) confirmed the existence of iron-BODIPY complex (Figure S4).…”

“…As displayed in Figure 7, the hydrazone proton signal (H 4 ) at 8.06 ppm completely disappeared and the amine proton resonance (H 5 ) at 10.98 ppm almost completely disappeared upon the addition of Fe 3+ . The rest of the proton peaks of pyridylhydrazone moiety became broader indicating that Fe 3+ bound to the PH unit which is consistent with the previous findings [25,53,54] FT-IR spectroscopy was also carried out to confirm the complex formation between Fe 3+ and BODIPY-PH (Figure 8). For the BODIPY-PH spectrum, the characteristic peaks at 3181, 2978, 2926, 1597, and 1584 cm −1 were assigned to N-H, Cmethyl-H, Cmethyl-H, C=N, and C=N stretching vibrations, respectively.…”

“…As part of our continuing interest in the development of boron-based imaging agents [22][23][24], we decided to synthesize a novel fluorescence compound based on boron difluoride dipyrromethene (BODIPY) and functionalize it with a pyridylhydrazone (PH) unit acting as a metal-binding site (Figure 1). Although the capability of PH unit in Fe 3+ complexation has been demonstrated in pyrene-based compounds (I), the sensing properties of the PH-functionalized fluorescent probe toward ferric ions have not been systematically reported elsewhere [25]. Apart from metal binding, the PH moiety is involved in reaction-based fluorescence turn-on sensor for Au 3+ ions and hypochlorous acid (HOCl) in BODIPY (II) and rhodamine (III) backbones, respectively (Figure 1) [26,27].…”

Real‐Time Probe for the Efficient Sensing of Inorganic Fluoride and Copper Ions in Aqueous Media

“…Furthermore, this limitation could be a great set back to use these probes in field studies. Therefore, designing a probe which could detect ions present in aqueous media is of high interest ,. Furthermore, preparation of inorganic‐organic hybrid materials for the detection of cations in real‐time is of considerable interest.…”

“…Therefore, designing a probe which could detect ions present in aqueous media is of high interest. [45,46] Furthermore, preparation of inorganic-organic hybrid materials for the detection of cations in real-time is of considerable interest. Thus, there are few reports based on adsorption of these probes on silica microspheres for the detection of cations.…”