Early events in 2,4,6-trinitrotoluene (TNT) degradation by porphyrins: Binding of TNT to porphyrin by hydrophobic and hydrogen bonds

Hikal, Walid M.; Harmon, H. James

doi:10.1016/j.jhazmat.2007.10.098

Cited by 18 publications

(13 citation statements)

References 34 publications

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“…Meanwhile, a trough (decrease in absorbance) at 420 nm and a peak (absorbance increase) at 462 nm are clearly observed when we subtract the PCN-224 absorbance spectrum from the PCN-224 + TNT absorbance spectrum (point-to-point subtraction) ( Figure S15B, Supporting Information), probably attributing to the formation of a TCPP-TNT complex. 13 This variation trend is similar to the reported free porphyrin molecule sensor through static quenching mechanism for TNT detection. 12,13 Additionally, with the increase of TNT addition, these changes become more visible, indicating that more TNT-porphyrin complex is produced.…”

Section: Resultssupporting

confidence: 87%

Rapid and Specific Aqueous-Phase Detection of Nitroaromatic Explosives with Inherent Porphyrin Recognition Sites in Metal–Organic Frameworks

Yang

Wang

et al. 2015

ACS Appl. Mater. Interfaces

138

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Development of a rapid and effective method for the detection of 2,4,6-trinitrotoluene (TNT) in aqueous phase has attracted great attention. In this work, the fluorescent porphyrin-based metal-organic frameworks (MOFs) of PCN-224 were successfully exploited as a fluorescent probe for the rapid and selective TNT detection in water media. This strategy combined the advantages of fluorescent porphyrin molecules and porous MOFs, which not only overcame the aggregation of hydrophobic tetrakis(4-carboxyphenyl)porphyrin (TCPP) recognition sites but also promoted TNT to interact with recognition sites in virtue of the high surface and intrinsic open structure of MOFs. As a result, a rapid response time of as short as 30 s was obtained for the elaborated fluorescent probe. Meanwhile, the bright red emission of porphyrin units in PCN-224 could be proportionally quenched in correlation with the applied TNT level through the formation of TNT-TCPP complex in the ground state. The specificity of the employed sensory platform for TNT recognition was scarcely affected by other possible coexistent interfering species. Furthermore, this fluorescent PCN-224 probe presented a much higher quenching efficiency for TNT than other structurally similar nitroaromatic compounds and was successfully applied for the quantitative detection of TNT in the mixed nitroaromatic explosive samples. This prefigured their great potentials of practical TNT detection in water media for public safety and security.

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Section: Resultssupporting

confidence: 87%

Rapid and Specific Aqueous-Phase Detection of Nitroaromatic Explosives with Inherent Porphyrin Recognition Sites in Metal–Organic Frameworks

Yang

Wang

et al. 2015

ACS Appl. Mater. Interfaces

138

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“…Hikal and Harmon also used meso-tri(4-sulfonatophenyl)mono(4-carboxyphenyl) porphyrin (C 1 TPP) for the fluorogenic detection of TNT in water. 94 At this respect water solutions at pH 7.0 of C 1 TPP presented an intense absorption band in the Soret region at 413 nm. Addition of increasing quantities of TNT induced a reduction of the extinction coefficient of the band centred at 413 nm together with the apparition of a broad shoulder centred at 424 nm.…”

Section: Heterocyclesmentioning

confidence: 85%

Optical chemosensors and reagents to detect explosives

et al. 2012

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“…The interaction between porphyrins and TNT was further explored by UV-vis and fluorescence spectroscopy, which suggested binding of TNT to the pyrrole nitrogens in porphyrins via hydrogen bonds. 135 A series of porphyrins doped porous silica films were developed by Li et al with high fluorescence quenching efficiencies towards NAC vapors. [136][137][138] Porphyrins were directly incorporated onto the silica surface through co-condensation of porphyrinfunctionalized silanes with tetraethoxylsilane (TEOS).…”

Section: Small Molecule Fluorophores For Explosive Detectionmentioning

confidence: 99%

Fluorescence based explosive detection: from mechanisms to sensory materials

2015

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The detection of explosives is one of the current pressing concerns in global security. In the past few decades, a large number of emissive sensing materials have been developed for the detection of explosives in vapor, solution, and solid states through fluorescence methods. In recent years, great efforts have been devoted to develop new fluorescent materials with various sensing mechanisms for detecting explosives in order to achieve super-sensitivity, ultra-selectivity, as well as fast response time. This review article starts with a brief introduction on various sensing mechanisms for fluorescence based explosive detection, and then summarizes in an exhaustive and systematic way the state-of-the-art of fluorescent materials for explosive detection with a focus on the research in the recent 5 years. A wide range of fluorescent materials, such as conjugated polymers, small fluorophores, supramolecular systems, bio-inspired materials and aggregation induced emission-active materials, and their sensing performance and sensing mechanism are the centerpiece of this review. Finally, conclusions and future outlook are presented and discussed.

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Early events in 2,4,6-trinitrotoluene (TNT) degradation by porphyrins: Binding of TNT to porphyrin by hydrophobic and hydrogen bonds

Cited by 18 publications

References 34 publications

Rapid and Specific Aqueous-Phase Detection of Nitroaromatic Explosives with Inherent Porphyrin Recognition Sites in Metal–Organic Frameworks

Rapid and Specific Aqueous-Phase Detection of Nitroaromatic Explosives with Inherent Porphyrin Recognition Sites in Metal–Organic Frameworks

Optical chemosensors and reagents to detect explosives

Fluorescence based explosive detection: from mechanisms to sensory materials

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