Pyrazoline-based colorimetric and fluorescent probe for detection of sulphite

Uchacz, Tomasz; Jajko, Gabriela; Danel, Andrzej; Szlachcic, Paweł; Zapotoczny, Szczepan

doi:10.1039/c8nj05017a

Cited by 30 publications

(9 citation statements)

References 36 publications

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“…This result indicates that a large charge separation occurred in the neutral form of 4 , whereas no charge separation occurred in the protonated form of 4 . This further suggests that protonated and unprotonated 4 prefer the locally excited (LE) character in the excited state and ICT process, respectively. , Therefore, the LE characteristics of the protonated species of 4 formed in MeOH were strong even in polar solvents such as MeOH without emission quenching through the TICT state.…”

Section: Resultsmentioning

confidence: 96%

“…This further suggests that protonated and unprotonated 4 prefer the locally excited (LE) character in the excited state and ICT process, respectively. 37,38 Therefore, the LE characteristics of the protonated species of 4 formed in MeOH were strong even in polar solvents such as MeOH without emission quenching through the TICT state.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpK_a of Methanol and Ethanol

et al. 2022

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An optical pH probe is a simple and effective tool for determining an accurate pH value in its localized area. However, basic pH probes with pK BH+ values above 8 have rarely been reported, although many components with high pK a such as arginine play important roles in vivo. Herein, we introduce novel colorimetric and fluorescent basic probes 1–5, which are designed using push–pull-type aminoquinoline and aminobenzoquinoline fluorophores, with pK BH+ values ranging from 8.4 to 9.9. After the basicity of the remarkably sensitive basic probe 4 was tuned, it was able to successfully distinguish between the pK a values of MeOH (15.5) and EtOH (15.9), thus displaying selective protonation and fluorescence enhancement in MeOH over EtOH. Our pH probes can be used to detect MeOH poisoning in commercial EtOH products such as hand sanitizers, providing an effective solution to this problem observed during the COVID-19 pandemic.

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Section: Resultsmentioning

confidence: 96%

Section: ■ Results and Discussionmentioning

confidence: 99%

Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpK_a of Methanol and Ethanol

et al. 2022

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“…Pyrazoline derivatives as a kind of important five-member nitrogen-containing compound are ubiquitous in natural products. , With the CNNHC functional group, pyrazoline derivatives possess a broad spectrum of biological activities and have attracted considerable interests in functional materials such as medicine, − fluorescent substances, − and energetic fuel precursors. , …”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃

Xia

Zhang²,

Liu

et al. 2020

Ind. Eng. Chem. Res.

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Pyrazoline derivatives as valuable five-membered heterocyclic compounds could be readily prepared through the intramolecular cyclization of ketazines. In this paper, transition metals (Zn 2+ , Cu 2+ , Cr 3+ , Mn 2+ , Co 2+ , Ni 2+ , and Fe 3+ ) were applied for the catalytic synthesis of 3,5,5-trimethyl-2-pyrazoline, and FeCl 3 showed the best catalytic performance with 95% conversion and 99% selectivity. Substrate screening exhibited that the steric hindrance of ketazines is a key factor on the conversions of R-substituted pyrazolines, following the order of R as methyl (95%) > ethyl (83%) > propyl (68%) > butyl (55%). Moreover, the mechanism of the cyclization of ketazines catalyzed by FeCl 3 is calculated by density functional theory. The energetic profile shows that the cyclization reaction consists of two steps and FeCl 3 can efficiently reduce their barrier energies. This work provides a feasible method for the preparation of pyrazoline derivatives using inexpensive, less toxic, and environmentally friendly FeCl 3 as a catalyst.

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“…Nevertheless, the practical application of the probes was illustrated by utilizing a paper test strip method for HSO 3 − detection. It was observed that the paper discolored from orange or yellow to blue [ 104 ], confirming its potentiality to detect HSO 3 − in water samples. In this study, a simple replacement of end groups by thiophene surpassed the response time by 1.2 times and the detection limit by 1.5 times.…”

Section: Fluoridementioning

confidence: 96%

A Comprehensive Review on Thiophene Based Chemosensors

et al. 2021

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The recognition and sensing of various analytes in aqueous and biological systems by using fluorometric or colorimetric chemosensors possessing high selectivity and sensitivity, low cost has gained enormous attention. Furthermore, thiophene derivatives possess exceptional photophysical properties compared to other heterocycles, and therefore they can be employed in chemosensors for analyte detection. In this review, we have tried to explore the design and detection mechanism of various thiophene-based probes, practical applicability, and their advanced models (design guides), which could be thoughtful for the synthesis of new thiophene-based probes. This review provides an insight into the reported chemosensors (2008-2020) for thiophene scaffold as effective emission and absorption-based chemosensors.

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Pyrazoline-based colorimetric and fluorescent probe for detection of sulphite

Abstract: This work reports a novel Michael addition based sensor for fluorescence detection of sulphite in river water samples.

Cited by 30 publications

References 36 publications

Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpK_a of Methanol and Ethanol

Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpK_a of Methanol and Ethanol

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃

A Comprehensive Review on Thiophene Based Chemosensors

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Pyrazoline-based colorimetric and fluorescent probe for detection of sulphite

Abstract: This work reports a novel Michael addition based sensor for fluorescence detection of sulphite in river water samples.

Cited by 30 publications

References 36 publications

Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpKa of Methanol and Ethanol

Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpKa of Methanol and Ethanol

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl3

A Comprehensive Review on Thiophene Based Chemosensors

Contact Info

Product

Resources

About

Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpK_a of Methanol and Ethanol

Basic Fluorescent Protonation-Type pH Probe Sensitive to Small ΔpK_a of Methanol and Ethanol

Highly Efficient Conversion of Ketazines to Pyrazoline Derivatives Catalyzed by FeCl₃