An acidic pH fluorescent probe based on Tröger's base

Yuan, Chunxue; Zhang, Yanmin; Xi, He; Tao, Xiaofeng

doi:10.1039/c7ra11228a

Cited by 21 publications

(21 citation statements)

References 33 publications

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“…Most fluorescence pH probes are practical in a near-neutral pH region, and probes for detecting the pH changes in the acidic range are limited [55]. Moreover, fluorescence pH sensors are still subject to limitations based on their limited photostability.…”

Section: Applicability Of 26-diphenylpyridine Derivatives As Fluoresmentioning

confidence: 99%

Double Role of Diphenylpyridine Derivatives as Fluorescent Sensors for Monitoring Photopolymerization and the Determination of the Efficiencies of the Generation of Superacids by Cationic Photoinitiators

Topa

Petko²,

Galek³

et al. 2020

Sensors

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Novel fluorescent sensors with electron-donating or electron-withdrawing substituents incorporated into a chromophore group based on 2,6-diphenylpyridine were designed and synthesised. The spectroscopic properties of these compounds were studied. Moreover, the positive solvatochromism of 2,6-bis-(4-methylsulphanylphenyl)pyridine (PT-SCH3) in selected solvents was studied by measurement of the absorption and emission spectra and analysed using the Dimroth–Reichardt solvent parameter set. After that, the performance of a series of 2,6-diphenylpyridine derivatives as fluorescent molecular sensors for monitoring free-radical and cationic photopolymerization processes by the Fluorescence Probe Technique (FPT) was studied. As a consequence of this stage of research, the effect of substituents on the sensitivity of the 2,6-diphenylpyridine derivatives as sensors during photopolymerization has been evaluated and discussed. It has been found that compounds containing strong electron-donating substituent (PT-SCH3) slightly shift their fluorescence spectrum during the free-radical polymerization of monomer, which enables the monitoring of the polymerization progress using the fluorescence intensity ratio measured at two different wavelengths as the progress indicator. The position of the fluorescence spectrum of 2,6-diphenylpyridine derivatives with electron-withdrawing substituents is practically insensitive to changes occurring in their environment. Hence, it is recommended to use these compounds with different indicators of the progress of the photopolymerization process based on normalised intensity of fluorescence (Imax/I0). Among the compounds studied, 2,6-bis(4-methylsulphanylphenyl)pyridine (PT-SCH3) turned out to be the best fluorescent sensor for the purpose of monitoring free-radical polymerization by FPT. Consequently, the dual application of the selected 2,6-diphenylpyridine derivatives is proposed: (a) as fluorescent sensors for monitoring the free-radical photopolymerization progress, and (b) as spectroscopic sensors for the determination of efficiencies of the generation of superacids by cationic photoinitiators during the cationic photopolymerization process. Finally, a new method for determining the relative efficiency of the photogeneration of superacids during the photo cleavage of onium salt has been devised and applied for the evaluation of the performance of 2,6-diphenylpyridine derivatives.

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Section: Applicability Of 26-diphenylpyridine Derivatives As Fluoresmentioning

confidence: 99%

Double Role of Diphenylpyridine Derivatives as Fluorescent Sensors for Monitoring Photopolymerization and the Determination of the Efficiencies of the Generation of Superacids by Cationic Photoinitiators

Topa

Petko²,

Galek³

et al. 2020

Sensors

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“…Such behavior enables it to work as a fluorescent turn-off pH sensor in solution state. 1H NMR spectroscopy analysis suggests that the change in electron affinity of the pyridinyl unit upon protonation and deprotonation is responsible for such sensing processes [11].…”

Section: Related Researchmentioning

confidence: 99%

Development of pH Sensing Devices Based on Optical Fluorescents with Rapid Measurement, Low Cost and Wireless Monitoring

Siregar

Mujiono

2020

JAREE

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The level of acid or base in water based on solution (pH) is a very important measure for living things because about 70% in the body consists of water. Most of the metabolism in the body requires a certain pH level. Having a rapid and accurate pH meter is very demanding, but most of the available pH meters take several minutes to measure the pH of the liquid. The measured water is mixed with fluorescent liquid and then excited with violet light at a wavelength of 405 nm. We have developed a pH meter based on optical fluorescent using pyranine extracted from yellow highlighter using isopropyl alcohol. The pH meter based on optical fluorescent have advantage compared to other methods in terms of measurement time. The intensity of the green fluorescent emitted from the liquid sample is then captured by the AS7262 spectral sensor. A pH sensing device has been developed, tested and verified to be able to measure pH from a range of 4 to 11 with an accuracy of 98.13%, a reading error value of ±0.13 and only takes less than 3 seconds to take measurements.

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“…Up to now, several strategies concerning the molecular design have been developed to promote stimuli‐responsive fluorescent materials performances, like adopting donor‐acceptor systems that have readily perturbed twisted structure and relatively loose arrangement . Hence, a large number of stimuli‐responsive fluorescent materials have been reported, including mechanochromic (MC) materials, thermal‐stimuli responsive materials, pH‐stimuli responsive materials and so on . In addition, picric acid (PA), as an external stimulus, which is one of the main nitroaromatics (NACs) and widely applied in explosives, dyes and other field.…”

Section: Introductionmentioning

confidence: 99%

Conformation of D‐π‐A Molecular with Functional Imidazole Group: Achieving High Color Contrast Mechanochromic Behavior and Selectively Detection of Picric Acid in Aqueous Medium

et al. 2019

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Multi‐stimuli responsive D‐π‐A molecular (named CZIZ) comprising of carbazole as D, dicyano as A and imidazole as functional group was designed and synthesized. The photophysical properties showed that CZIZ possessed the property of aggregation‐induced emission enhancement (AIEE) property, which was verified by UV‐vis absorption and fluorescence spectra. In addition, the large twisted structure and loose arrangement induced CZIZ performed high color contrast mechanochromic (MC) behaviors from 537 nm to 584 nm, which was successfully applied in ink‐free rewritable paper. Furthermore, CZIZ showed high selective detection for picric acid (PA) in aqueous medium due to the excellent proton‐binding property of the imidazole group, which was verified by1H NMR spectra. The density functional theory verified that the fluorescent quenching mechanism is a photoinduced electron transfer (PET) process between CZIZ and PA. The compound CZIZ described herein will efficiently expand the development of design principles to supply diverse multifunctional tools for material science and material engineering.

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An acidic pH fluorescent probe based on Tröger's base

Abstract: A pH fluorescent probeTBPPincorporating an amine moiety and pyridine group through Tröger's base linker was designed and synthesized. The absorption and fluorescence titrations indicated that it can serve as a sensitive probe for pH measuring.

Cited by 21 publications

References 33 publications

Double Role of Diphenylpyridine Derivatives as Fluorescent Sensors for Monitoring Photopolymerization and the Determination of the Efficiencies of the Generation of Superacids by Cationic Photoinitiators

Double Role of Diphenylpyridine Derivatives as Fluorescent Sensors for Monitoring Photopolymerization and the Determination of the Efficiencies of the Generation of Superacids by Cationic Photoinitiators

Development of pH Sensing Devices Based on Optical Fluorescents with Rapid Measurement, Low Cost and Wireless Monitoring

Conformation of D‐π‐A Molecular with Functional Imidazole Group: Achieving High Color Contrast Mechanochromic Behavior and Selectively Detection of Picric Acid in Aqueous Medium

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