Methods for Detecting Picric Acid—A Review of Recent Progress

Fabin, Magdalena; Łapkowski, Mieczysław; Jarosz, Tomasz

doi:10.3390/app13063991

Cited by 14 publications

(4 citation statements)

References 127 publications

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“…Thus, selective sensing of PA has gained a prominence. 56 Q5 also showed its potential for naked-eye detection of PA under a UV lamp. With gradual addition of PA (1.5 mM) to Q5, the compound's mild orange fluorescence steadily diminished, and it eventually became nonfluorescent (Figure 6c).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Synthesis of p-Azaquinodimethane-based Quinoidal Fluorophores

2023

J. Org. Chem.

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Quinoidal π-conjugated systems are sought-after materials for semiconducting applications because of their rich optical and electronic characteristics. However, the analogous fluorescent compounds are extremely rare, with just two reports in the literature. Here, we present the design and development of a third series of quinoidal fluorophores [(2,5-diarylidene)-3,6-bis(hexyloxy)-2,5-dihydropyrazine (Q1–Q5)] that incorporates p-azaquinodimethane. The fluorophores are synthesized in a two-step synthetic approach employing Knoevenagel condensation of N,N-diacetyl-piperazine-2,5-dione with different aromatic aldehydes followed by O-alkylation in high yields. Q1–Q5 are strongly emissive, and by altering the aryl-substituents, the emission colors can be modulated from blue to orange. The compounds possess emission maxima (λem) at 475–555 nm in the solution state and 510–610 nm in the solid state, with fluorescence quantum yields of up to 60%. To the best of our knowledge, the reported systems are the first quinoidal dual-state emissive (solution- and solid-state) compounds. In trifluoroacetic acid, Q5 exhibits halochromic behavior, with a dramatic color change from yellow to blue. Furthermore, the preliminary fluorescent sensing studies demonstrated that Q5 could act as a selective turn-off fluorescence probe for electron-deficient picric acid (PA), with an emission quenching of >90% in the solution state. The thin-layer chromatography (TLC) strip sensor of Q5 was also designed to detect PA in water.

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…PA has been widely employed in producing medicines, dyes, insecticides, and rocket propellants, but its high water solubility and high toxicity, even at trace-level concentrations, raise serious concerns for human health and environmental contamination. Thus, selective sensing of PA has gained a prominence …”

Section: Resultsmentioning

confidence: 99%

Synthesis of p-Azaquinodimethane-based Quinoidal Fluorophores

2023

J. Org. Chem.

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“…To overcome these limitations, molecules incorporating imidazole with a basic nitrogen atom attracted us toward their facile synthesis (one-pot reaction), and it promotes distinct emission behavior after the interaction with nitro explosives. However, most of the receptors exhibit fluorescence quenching response toward explosives through a photoinduced electron transfer (PET) mechanism − or energy transfer mechanism. − Turn-off fluorescence sensing is inferior to turn-on or ratiometric fluorescence detection, as the former is efficiently inhibited by instabilities in background fluorescence, resulting in a lack of reliability. Hence, there is a crucial need to develop a fluorophore with desired characteristics such as significant Stokes shift, high quantum yield, ratiometric optical response, and greater selectivity for developing a vital fluorescent probe for the detection of target analytes.…”

Section: Introductionmentioning

confidence: 99%

D–π–A–π–D-Configured Imidazole-Tethered Benzothiadiazole-Based Sensor for the Ratiometric Discrimination of Picric Acid: Applications in Latent Fingerprint Imaging

Manoj Kumar,

Kulathu Iyer

2024

J. Org. Chem.

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A tetraphenyl imidazole-appended benzothiadiazole-based fluorogenic probe (4,7-bis(4-(1,4,5-triphenyl-1H-imidazol-2-yl)phenyl)benzo [c][1,2,5]thiadiazole (BIPT)) has been successfully synthesized and characterized by NMR and high-resolution mass spectrometry (HRMS) spectral analyses. A low limit of detection (LOD) can be achieved to detect picric acid (PA; 7.89 nM). When benzothiadiazole acceptors are incorporated in the D−A−D probe, it can produce a large Stokes shift (206 nm) as a result. Fascinatingly, the fluorescence signals of BIPT were ratiometrically induced by the interaction with PA and exhibited an apparent emission shift from pink to green. The detection process of BIPT is triggered by an intermolecular charge transfer process, as the charge transfer takes place from the electron-rich imidazole to the electron-deficient PA. Moreover, fluorescence detection of PA has been employed in paper strips. Advantageously, sensor BIPT can potentially be applied to contact mode and real-time detection of PA in environmental water samples. Additionally, the BIPT sensor has been successfully employed for latent fingerprint imaging. The study provides clear insights into the rational design of chemosensors for sensing and real-time applications.

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“…[ 62–67 ] In contrast, a significant number of picric acid explosive sensors are known from emissive crystalline materials. [ 60,61,68 ] Surprisingly, the sensing functionalities of halogen‐bonded cocrystals for acid vapors and picric acid explosive have not been explored yet to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

A Halogen‐Bonded Organic Framework (XOF) Emissive Cocrystal for Acid Vapor and Explosive Sensing, and Iodine Capture

Maji

Natarajan

2023

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There is a strong and urgent need for efficient materials that can capture radioactive iodine atoms from nuclear waste. This work presents a novel strategy to develop porous materials for iodine capture by employing halogen bonding, mechanochemistry and crystal engineering. 3D halogen‐bonded organic frameworks (XOFs) with guest‐accessible permanent pores are exciting targets in crystal engineering for developing functional materials, and this work reports the first example of such a structure. The new‐found XOF, namely TIEPE‐DABCO, exhibits enhanced emission in the solid state and turn‐off emission sensing of acid vapors and explosives like picric acid in nanomolar quantity. TIEPE‐DABCO captures iodine from the gas phase (3.23 g g−1 at 75 °C and 1.40 g g−1 at rt), organic solvents (2.1 g g−1), and aqueous solutions (1.8 g g−1 in the pH range of 3–8); the latter with fast kinetics. The captured iodine can be retained for more than 7 days without any leaching, but readily released using methanol, when required. TIEPE‐DABCO can be recycled for iodine capture several times without any loss of storage capacity. The results presented in this work demonstrate the potential of mechanochemical cocrystal engineering with halogen bonding as an approach to develop porous materials for iodine capture and sensing.

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Methods for Detecting Picric Acid—A Review of Recent Progress

Cited by 14 publications

References 127 publications

Synthesis of p-Azaquinodimethane-based Quinoidal Fluorophores

Synthesis of p-Azaquinodimethane-based Quinoidal Fluorophores

D–π–A–π–D-Configured Imidazole-Tethered Benzothiadiazole-Based Sensor for the Ratiometric Discrimination of Picric Acid: Applications in Latent Fingerprint Imaging

A Halogen‐Bonded Organic Framework (XOF) Emissive Cocrystal for Acid Vapor and Explosive Sensing, and Iodine Capture

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