Oxacalix[4]arene based dual-signalling fluorimetric and electrochemical chemosensor for the selective detection of nitroaromatic compounds

Vora, Manoj; Panchal, Manthan; Dey, Sudip; Pandya, Alok; Athar, Mohd; Verma, Nidhi; Ahmad, Ishfaq; Jain, V. K.

doi:10.1016/j.molliq.2022.119791

Cited by 7 publications

(6 citation statements)

References 51 publications

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“…Owing to critical problems related to national security and environmental safety, selective detection of nitro explosives has attracted significant interest recently. − Picric acid (PA) is widely used as a reagent in chemical industries, leather products, and dyes . However, PA causes severe health hazards such as skin irritation, headache, and respiratory disorders .…”

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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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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“…At this point, fluorescent chemosensors appear as a reliable method that can satisfy these needs. Due to their electron-poor nature, explosives can interact with electron-rich fluorescent probes, providing significant fluorescence quenching with electron and charge transfer mechanisms. , …”

Section: Introductionmentioning

confidence: 99%

Application of aza-BODIPY as a Nitroaromatic Sensor

Sadikogullari,

Koramaz,

Sütay

et al. 2023

ACS Omega

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Nitroaromatic explosive detection with high sensitivity and selectivity is requisite for civilian and military safety and the ecosystem. In this study, aza boron dipyrromethene (aza-BODIPY) dye was selected as a fluorescent-based chemosensor against nitroaromatic compounds (NACs) including 2,4,6-trinitrophenol (picric acid, TNP), 2,4,6-trinitrotoluene (TNT), and 2,4-dinitrotoluene (DNT). This dye molecule exhibits sharp fluorescent behavior with high quantum yields beyond the near-infrared region (NIR) and is considered as a potential candidate for the detection of NACs. O’Shea’s approach was used to synthesize tetraphenyl-conjugated aza-BODIPY molecules. Quenching of fluorescence emission of aza-BODIPY at 668 nm after the exposure to NACs was investigated under acetonitrile–water and acetonitrile–ethanol solvent conditions. The quenching responses and its mechanism were examined by considering the Stern–Volmer relationship Stern–Volmer constants (K sv) for TNP (in water), TNP (in ethanol), TNT, and DNT, which are predicted to be 1420, 1215, 1364, and 968 M–1, respectively, all of which are sufficiently above the limit of detection (LOD) values. Thus, the present study opens up the possibility of the usage of aza-BODIPY molecules as a low-cost, light-weight sensor for the detection of NAC explosives.

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“…At present, the commonly used analytical methods for the detection of o ‐NP include high‐performance liquid chromatography, 4 flow injection analysis, 5 electrochemical analysis, 6 capillary electrophoresis, 7 and gas chromatography‐mass spectrometry 8 . But these methods are generally expensive instruments, complicated process, high detection cost, cannot reach the extent of large‐scale application, and fluorescence detection due to its simple operation, low cost, high sensitivity, good selectivity, real‐time detection, and many other advantages, is considered as one of the most excellent and most promising methods to detect o ‐NP 9,10 …”

Section: Introductionmentioning

confidence: 99%

The synthesis of triazine‐based conjugated microporous polymers via nucleophilic substitution reactions for fluorescence sensing to o‐nitrophenol

Wang

Tong-mou

2023

J of Applied Polymer Sci

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O‐nitrophenol (o‐NP) is a toxic substance that pollutes the environment and harms human health. Therefore, the development of materials for the efficient detection of o‐NP has attracted the attention of researchers in recent years. Triazine‐based porous organic materials are a kind of porous polymer materials with broad application prospects because of their physical and chemical stability. In this paper, two triazine‐based conjugated microporous polymers (CMPs) containing π‐π conjugated structures, TDAPT and HDAPT, are prepared by nucleophilic substitution reactions with the yields of 89.9% and 67.7%, respectively. Through a series of characterization, it is found that both triazine‐based CMPs have good chemical and thermal stabilities, and high pore properties, and their Brunauer–Emmett–Teller (BET) surface areas are as high as 1314 and 1315 m2 g−1, respectively. At the same time, the fluorescence sensing abilities of TDAPT and HDAPT are studied. The results show that both TDAPT and HDAPT have high sensitivities to o‐NP, their KSV values are 9.8 × 103 and 9.7 × 103 L mol−1 and limits of detection (LODs) are 7.42 × 10−11 and 8.17 × 10−11 mol L−1, respectively. The fluorescence quenching of TDAPT by o‐NP is only caused by the electron transfer mechanism, while the fluorescence quenching of HDAPT by o‐NP has both the electron transfer mechanism and the energy transfer mechanism.

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Oxacalix[4]arene based dual-signalling fluorimetric and electrochemical chemosensor for the selective detection of nitroaromatic compounds

Cited by 7 publications

References 51 publications

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

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

Application of aza-BODIPY as a Nitroaromatic Sensor

The synthesis of triazine‐based conjugated microporous polymers via nucleophilic substitution reactions for fluorescence sensing to o‐nitrophenol

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