An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent

Cicekbilek, Fulya; Yılmaz, Bahar; Bayrakcı, Mevlüt; Gezici, Orhan

doi:10.1007/s10895-019-02462-5

Cited by 21 publications

(6 citation statements)

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“…This downfield shift of -HCN protons of RH-DMAC (donar) in the presence of Au 3+ manifests the charge transfer between RH-DMAC and Au 3+ . Moreover, the signals attributed to benzene protons were observed to be broadened upon the addition of the Au 3+ ion and this was attributed to the ring-opening reaction of the spirolactum moiety in the rhodamine framework . As a result, the existence of noncovalent interactions between the fluorophore RH-DMAC and Au 3+ changed the position and shape of the proton signals in 1 H NMR spectra.…”

Section: Resultsmentioning

confidence: 98%

“…Moreover, the signals attributed to benzene protons were observed to be broadened upon the addition of the Au 3+ ion and this was attributed to the ringopening reaction of the spirolactum moiety in the rhodamine framework. 51 As a result, the existence of noncovalent interactions between the fluorophore RH-DMAC and Au 3+ changed the position and shape of the proton signals in 1 H NMR spectra. Furthermore, the ESI-MS analysis was conducted to corroborate the sensing mechanism.…”

Section: Effect Of Phmentioning

confidence: 99%

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AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au³⁺ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

et al. 2023

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In this study, a novel rhodamine-based optically and electrochemically active chemosensor, integrated with a p-DMAC moiety, demonstrated extremely selective identification of Au3+ ions relative to other metal species, including (Li+, Na+, K+, Ba2+, Ca2+, Mg2+, Co2+, Mn2+, Zn2+, Pb2+, Ni2+, Fe2+, Hg2+, Fe3+, Cd2+, Pd2+, Al3+, Cr3+, Cu2+, and nitrate salt of Ag+). These compounds demonstrated a novel and outstanding aggregation-induced emission enhancement (AIEE) behavior by aggregating in DMF/H2O medium. Furthermore, the degree of quenching was varying linearly with a Au3+ concentration from 0 to 40 nM, with a lower detection limit by RH-DMAC nanoaggregates of 118.79 picomolar (40.35 ppm). The Stern–Volmer plots, Job’s plot, Benesi–Hildebrand plot, 1H NMR titrations, ESI-mass, and FTIR all revealed significant interactions between the sensor and Au3+. Moreover, the proposed electrochemical sensor afforded a linear correlation before the peak current and concentration of Au3+ in the range of 0–40 nM, with a detection limit of 483.73 pM or 164.36 ppt (by cyclic voltammetry method) and 298.0 pM or 101.24 ppt (by the Differential Pulse Voltammetry method). Furthermore, the proposed sensing assay was used to measure Au3+ ion in spiked water samples (tap, drinking, waste, and river water), achieving acceptable accuracy and precision with high recovery rates. Furthermore, RH-DMAC-coated fluorescence paper test strips were designed for on-site Au3+ detection. Apart from this, the use of smartphone-based RGB (Red Green Blue) color analysis shortened the operating process, accelerated the detection technique, and provided a novel methodology for the instantaneous, real-time examination of Au3+ in real water samples.

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Section: Resultsmentioning

confidence: 98%

Section: Effect Of Phmentioning

confidence: 99%

AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au³⁺ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

et al. 2023

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“…MCF7 cells were incubated with 10μM of Al 3+ ions in the culture medium at37 ο C for 1 h and washed with phosphate buffered saline (PBS)followed by the addition of 20μM SB-2. Bright field and fluorescent images were taken from Leica DM3000 fluorescence microscopy (FM) (Cicekbilek et al, 2019). Antimicrobial susceptibility was tested by the disk diffusion method on LB and NB agar, according to the guidelines of the National Committee for Clinical Laboratory Standards (NCCLS) (Fiebelkorn et al, 2013).…”

Section: Biological Applicationsmentioning

confidence: 99%

Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application

Bayrakcı

Yılmaz

2020

Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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A series of facile optical probe has been easily developed by a one-step Schiff base type reaction of 2,4-dihydroxybenzaldehyde and ortho, meta or para aminophenol. Schiff base compounds as fluorescence sensor were utilized to identify metal ions by spectrophotometric techniques. The data of absorption and emission spectra displayed the extraordinary selective and sensitive sensor properties for Schiff base probe derived from ortho aminophenol (SB-2) toward Al 3+ ions. Upon introducing Al 3+ ions, an excellent increase in the fluorescence intensity of the probe (SB-2) resulting in color change was observed because of blocking the photoinduced electron transfer (PET) mechanism of azomethine unit. The specific bonding mode of probe (SB-2) with Al 3+ was verified by using a series of spectroscopic techniques such as FT-IR, 1 H NMR, and UV-vis (Job-plot data). The detection limit of probe (SB-2) toward Al 3+ was determined around 10 −7 M. Furthermore, cell imaging studies of probe (SB-2) were also performed and from these experiments, it was seen that the presence of even trace amounts of Al 3+ in living cells could be noticeably detected by (SB-2). In this study, antimicrobial properties of Schiff base compounds were also carried out towards some selected bacteria species. This presented work provides a method for design, facile synthesis and application of effective fluorescence probes toward Al 3+ ions in biological systems.

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“…After adding cations, these probes emitted a powerful fluorescence and showed a pink color because the cyclic structure of the spirolactam or spirolactone was opened through a reversible complexation or nonreversible chemical interaction. The above sensing mechanism has also been applied to construct rhodamine-based Hg 2+ fluorescent probes. − However, there are still more or less limitations for some of these Hg 2+ fluorescent probes including the delayed response, a narrow pH range, and cross interference. − Thus, developing unusual rhodamine-based fluorescent probes for Hg 2+ is still very important.…”

Section: Introductionmentioning

confidence: 99%

Rhodamine-Based Fluorescent Probe for Highly Selective Determination of Hg²⁺

Zhu

et al. 2022

ACS Omega

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The determination of mercuric ions (Hg 2+ ) in environmental and biological samples has attracted the attention of researchers lately. In the present work, a novel turn-on Hg 2+ fluorescent probe utilizing a rhodamine derivative had been constructed and prepared. The probe could highly sensitively and selectively sense Hg 2+ . In the presence of excessive Hg 2+ , the probe displayed about 52-fold fluorescence enhancement in 50% H 2 O/CH 3 CH 2 OH (pH, 7.24). In the meantime, the colorless solution of the probe turned pink upon adding Hg 2+ . Upon adding mercuric ions, the probe interacted with Hg 2+ and formed a 1:1 coordination complex, which had been the basis for recognizing Hg 2+ . The probe displayed reversible dual colorimetric and fluorescence sensing of Hg 2+ because rhodamine’s spirolactam ring opened upon adding Hg 2+ . The analytical performances of the probe for sensing Hg 2+ were also studied. When the Hg 2+ concentration was altered in the range of 8.0 × 10 –8 to 1.0 × 10 –5 mol L –1 , the fluorescence intensity showed an excellent linear correlation with Hg 2+ concentration. A detection limit of 3.0 × 10 –8 mol L –1 had been achieved. Moreover, Hg 2+ in the water environment and A549 cells could be successfully sensed by the proposed probe.

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An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent

Abstract: A facile synthesis procedure, whereby 9-Anthraldehyde (AA) is coupled to aminated rhodamine (AR) via a Schiff base-type reaction, is reported. The applicability and performance of the obtained material (AA-AR) as a sensing agent was studied towards 16 metal cations (i.

Cited by 21 publications

References 30 publications

AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au³⁺ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au³⁺ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application

Rhodamine-Based Fluorescent Probe for Highly Selective Determination of Hg²⁺

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An Application of a Schiff-Base Type Reaction in the Synthesis of a New Rhodamine-Based Hg(II)-Sensing Agent

Abstract: A facile synthesis procedure, whereby 9-Anthraldehyde (AA) is coupled to aminated rhodamine (AR) via a Schiff base-type reaction, is reported. The applicability and performance of the obtained material (AA-AR) as a sensing agent was studied towards 16 metal cations (i.

Cited by 21 publications

References 30 publications

AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au3+ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au3+ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

Synthesis and Spectroscopic Properties of Optical Probe Based on Schiff Base with Biological Application

Rhodamine-Based Fluorescent Probe for Highly Selective Determination of Hg2+

Contact Info

Product

Resources

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AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au³⁺ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

AIEE Active Azomethine-Based Rhodamine Derivative For Ultrasensitive Multichannel Detection of Au³⁺ Through a Fluorimetrically, Electrochemically, and RGB-Based Sensing Assay

Rhodamine-Based Fluorescent Probe for Highly Selective Determination of Hg²⁺