A highly sensitive and selective “off-on” porphyrin-based fluorescent sensor for detection of thiophenol

Chen, Guanfan; Tang, Mengzhuo; Fu, Xiufang; Cheng, Fenmin; Long, Yunfei; Li, Yuanyuan; Jiao, Yinchun; Zeng, Rongjin

doi:10.1016/j.molstruc.2018.10.097

Cited by 12 publications

(7 citation statements)

References 29 publications

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“…The LOD based on this was calculated to be 2.83 nM, which is much lower than the value in previous reports. 13,15,17 We have summarized the LOD and response time of the recently thiophenol probes in Table S2. Our probe has an LOD and response time that are comparable to previously reported values.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Long-term exposure to high concentrations of PhSH causes serious hazards, including dizziness, central nervous injury, muscle weakness, and even death. , Thus, development of simple and effective methods for distinguishing between toxic PhSH and biothiols is an important topic. Fluorescent probes have emerged as a fascinating approach in the detection of environmental pollutants because they have the advantages of high sensitivity, low cost, simple operation, and suitability for in vivo analysis. − Indeed, many fluorescent probes have been extensively developed for thiols. − …”

Section: Introductionmentioning

confidence: 99%

“…However, most of these fluorescent probes suffer from poor water solubility and require a large amount of organic solvents (≥30%, v/v). Moreover, the response time of these probes for detecting PhSH is too long (20–90 min) to meet the time requirement for their practical applications in environmental and biological samples. − Therefore, there is still an urgent need for fluorescent probes that have good water solubility, fast response time, and high sensitivity and selectivity for detecting PhSH.…”

Section: Introductionmentioning

confidence: 99%

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β-Cyclodextrin-Promoted Colorimetric and Fluorescence Turn-on Probe for Discriminating Highly Toxic Thiophenol from Biothiols

Zhao

et al. 2020

ACS Sustainable Chem. Eng.

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A complex that was composed of β-cyclodextrin (β-CD) and a flavone derivative (compound 5) was designed as a colorimetric and fluorescence turn-on probe to discriminate thiophenol (PhSH) from biothiols in environmental water samples. The probe worked via a combination of photoinduced electron transfer (PET) and excited-state intramolecular proton transfer (ESIPT) mechanisms. In this complex (β-CD-5), the 2,4-dinitrobenzenesulfonyl group efficiently quenched the fluorescence of compound 5 through a PET mechanism, and sulfonate was cleaved by PhSH to produce a compound that has strong fluorescence. Meanwhile, ESIPT fluorescence that originated from the flavone was observed. Significantly, β-CD improved the response time and sensitivity of compound 5 with respect to PhSH. Under optimized conditions, the response time was 5 min, and the limit of detection of β-CD-5 for PhSH was ∼2.8 nM. The outstanding sensing performance of β-CD-5 was demonstrated to be originated from the geometric match between compound 5 and β-CD and enrichment of PhSH in the β-CD cavity.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

β-Cyclodextrin-Promoted Colorimetric and Fluorescence Turn-on Probe for Discriminating Highly Toxic Thiophenol from Biothiols

Zhao

et al. 2020

ACS Sustainable Chem. Eng.

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“…In cases of Cys and Hcy, the generated NBD-SR can undergo subsequent intermolecular rearrangement with adjacent amine groups to form emissive NBD–NHR derivatives, while such a process cannot occur for H 2 S and GSH. Recently, Chen and Zeng et al synthesized an NBD-O-porphyrin (probe 79 ) (Figure 29b) by installing NBD onto a porphyrin dye at the aromatic ortho -position [160]. Interestingly, probe 79 displayed selective turn-on fluorescence toward PhSH.…”

Section: Probes Based On Other Recognition Moietiesmentioning

confidence: 99%

Recent Progress in the Development of Fluorescent Probes for Thiophenol

et al. 2019

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Thiophenol (PhSH) belongs to a class of highly reactive and toxic aromatic thiols with widespread applications in the chemical industry for preparing pesticides, polymers, and pharmaceuticals. In this review, we comprehensively summarize recent progress in the development of fluorescent probes for detecting and imaging PhSH. These probes are classified according to recognition moieties and are detailed on the basis of their structures and sensing performances. In addition, prospects for future research are also discussed.

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“…Usually, the fluorescent probe based on ESIPT has large Stokes shift, which effectively avoids interference from its own absorption and is widely used. Hence, many fluorescent probes based on ESIPT for PhSH have been reported [23][24][25][26][27][28][29][30]. Among them, fluorescent probes with near-infrared (NIR) emission have unique advantages in bioimaging especially.…”

Section: Introductionmentioning

confidence: 99%

The sensing mechanism of fluorescent probe for PhSH and the process of ESIPT

Zhang

Liu

et al. 2022

Photochem Photobiol Sci

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The detection mechanism of fluorescent probe FQ-DNP (DNP: 2,4-dinitropheno) for PhSH and the detailed ESIPT process of its product 2-(6-(diethylamino) quinolin-2-yl)-3-Hydroxy-4H-chromen-4-one (FQ-OH) have been revealed by density functional theory (DFT) and time-dependent density functional theory (TD-DFT). For FQ-OH, the decreased bond length of H 6 -N 7 and RDG analysis illustrate that the strength of hydrogen bond H 6 -N 7 has been enlarged after photoexcitation, creating a good condition for ESIPT. To illustrate the ESIPT process in detail, the potential energy curves are performed and the transition state reaction energy is calculated. In the S 0 state, the FQ-OH could happen proton transfer (PT) to form keto, but the keto form is more unstable than enol form. After photoexcitation, in the S 1 state, FQ-OH could happen PT to produce stable keto form. Excited dynamic simulation shows that PT happens at 71.5 fs. The calculated absorption and emission spectra are in agreement with the experimental data, and the calculated Stokes shift is 160 nm. Frontier molecular orbitals (FMOs) and hole-electron analysis show that twisted intramolecular charge transfer (TICT) is responsible for the fluorescent quenching of FQ-DNP.

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A highly sensitive and selective “off-on” porphyrin-based fluorescent sensor for detection of thiophenol

Cited by 12 publications

References 29 publications

β-Cyclodextrin-Promoted Colorimetric and Fluorescence Turn-on Probe for Discriminating Highly Toxic Thiophenol from Biothiols

β-Cyclodextrin-Promoted Colorimetric and Fluorescence Turn-on Probe for Discriminating Highly Toxic Thiophenol from Biothiols

Recent Progress in the Development of Fluorescent Probes for Thiophenol

The sensing mechanism of fluorescent probe for PhSH and the process of ESIPT

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