A diketopyrrolopyrrole-based near-infrared sensor for selective recognition of fluoride ions

Yang, Xiaofeng; Xie, Lijun; Rui, Ning; Gong, Xiaoqian; Liu, Zheng; Li, Yexin; Zheng, Luyi; Zhang, Gege; Gao, Bin; Cui, Yu; Sun, Guangmin; Zhang, Guangyou

doi:10.1016/j.snb.2015.01.025

Cited by 43 publications

(13 citation statements)

References 85 publications

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“…In light of their demand of instrument and pretreatment, they are not suitable for the rapid and low‐cost detection of organophosphorus pesticides. Fluorescence analysis method has attracted widespread attention in recent years in view of its fast response, high sensitivity and easy operation . In this regard, 1,8‐naphthalimide derivatives are a type of luminophore compounds which possess excellent optical properties, good chemical stability and easy modification.…”

Section: Methodsmentioning

confidence: 99%

A Naphthalimide‐Based Fluorescent Turn‐On Sensor for the Selective Detection of Diethyl Chlorophosphate

Zhang

Cao

et al. 2018

ChemistrySelect

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A naphthalimide derivative, named 4-(2-aminophenoxy)-N-(2ethylhexyl)-naphthalimide (AEN), was synthesized and characterized by NMR and ESI-MS. The photophysical behaviors of AEN toward diethyl chlorophosphate (DCP) were investigated by fluorescence spectrometry. Moreover, the detection mechanism of AEN for DCP was evaluated by 1 H, 31 P NMR and ESI-MS spectroscopy. These results show that the fluorescence intensity of AEN significantly increased with the augment of DCP concentration. No obvious interference with the DCP detection was observed in the presence of other common solvents (e. g. tetrahydrofuran, dimethyl sulfoxide, n-hexane, N,N-dimethylformamide, and isopropanol), phosphorus-containing reagents (e. g. dimethyl methylphosphonate, and triethyl phosphate), brominated compounds (1-bromobutane) and chlorinated compounds (e. g. 1,2-dichloroethane, chlorobenzene, carbon tetrachloride), indicating that AEN possesses satisfactory selectivity and sensitivity for the detection of DCP.

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Section: Methodsmentioning

confidence: 99%

A Naphthalimide‐Based Fluorescent Turn‐On Sensor for the Selective Detection of Diethyl Chlorophosphate

Zhang

Cao

et al. 2018

ChemistrySelect

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“…In DTITPE, the imidazole N-H bond length was calculated to be 1.009 Å, which elongated to 1.474 Å in the presence of F − ion as a result of hydrogen bond formation to give the complex DTITPE.F − (Figure 6). In the adduct DTITPE.F − (Scheme 2), the H--F bond length was calculated to be 1.025 Å, significantly shorter than characteristic H--F bond lengths, which typically range between 1.73 to 1.77 Å [63,64]. From geometrical aspects, it can be seen that the DTITPE, DTITPE.F − , and DTITPE − molecules are non-planar in nature with the tetraphenyl groups as well as the two thienyl groups existing in two different planes (Table S1) [65].…”

Section: Computational Studiesmentioning

confidence: 99%

Tetraphenylethylene-Substituted Bis(thienyl)imidazole (DTITPE), An Efficient Molecular Sensor for the Detection and Quantification of Fluoride Ions

et al. 2021

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Fluoride ion plays a pivotal role in a range of biological and chemical applications however excessive exposure can cause severe kidney and gastric problems. A simple and selective molecular sensor, 4,5-di(thien-2-yl)-2-(4-(1,2,2-triphenylvinyl)-phenyl)-1H-imidazole, DTITPE, has been synthesized for the detection of fluoride ions, with detection limits of 1.37 × 10−7 M and 2.67 × 10−13 M, determined by UV-vis. and fluorescence spectroscopy, respectively. The variation in the optical properties of the molecular sensor in the presence of fluoride ions was explained by an intermolecular charge transfer (ICT) process between the bis(thienyl) and tetraphenylethylene (TPE) moieties upon the formation of a N-H—F− hydrogen bond of the imidazole proton. The sensing mechanism exhibited by DTITPE for fluoride ions was confirmed by 1H NMR spectroscopic studies and density functional theory (DFT) calculations. Test strips coated with the molecular sensor can detect fluoride ions in THF, undergoing a color change from white to yellow, which can be observed with the naked eye, showcasing their potential real-world application.

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“…This causes a bathochromic shift in absorption from 520 to 700 nm and hypsochromic shift in emission from 660 to 510 nm. Similarly, deprotonation of a diketopyrrolopyrrole dye 156 [224] by fluoride was also caused a bathochromic shift of absorption from 504 to 771 nm, and a quenching of fluorescence at 598 nm. Unfortunately, DMSO had to be used as a co-solvent for both probes, so that they may not be suitable for measurements in aqueous solutions.…”

Section: Probes For Other Analytesmentioning

confidence: 99%

Long-wavelength analyte-sensitive luminescent probes and optical (bio)sensors

Staudinger

Borisov

2015

Methods Appl. Fluoresc.

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Long-wavelength luminescent probes and sensors become increasingly popular. They offer the advantage of lower levels of autofluorescence in most biological probes. Due to high penetration depth and low scattering of red and NIR light such probes potentially enable measurements in tissues and some of them have already reached a high level of reliability required for such applications. This review focuses on the recent progress in development and application of long-wavelength analyte-sensitive probes which can operate both reversibly and irreversibly. Photophysical properties, sensing mechanisms, advantages and limitations of individual probes are discussed.

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A diketopyrrolopyrrole-based near-infrared sensor for selective recognition of fluoride ions

Cited by 43 publications

References 85 publications

A Naphthalimide‐Based Fluorescent Turn‐On Sensor for the Selective Detection of Diethyl Chlorophosphate

A Naphthalimide‐Based Fluorescent Turn‐On Sensor for the Selective Detection of Diethyl Chlorophosphate

Tetraphenylethylene-Substituted Bis(thienyl)imidazole (DTITPE), An Efficient Molecular Sensor for the Detection and Quantification of Fluoride Ions

Long-wavelength analyte-sensitive luminescent probes and optical (bio)sensors

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