Benzo[ghi]perylene and coronene as ratiometric fluorescence probes for the selective sensing of nitroaromatic explosives

Hussain, Ejaz; Li, Yongxin; Cheng, Cheng; Zhuo, Huipeng; Shahzad, Sohail Anjum; Ali, Sajjad; Ismail, Muhammad; Qi, Hong; Yu, Cong

doi:10.1016/j.talanta.2019.120316

Cited by 25 publications

(16 citation statements)

References 22 publications

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“…16,17 These PAHs have been studied in the field of materials science because of their relationship with graphene 18 and to understand the behavior of phase transitions under extreme pressure and temperature conditions 19,20 or even to synthesize graphene nanoribbons by encapsulation. 21 Furthermore, PAHs have been explored in applications such as nano-sensors of oxygen, 22 detection of nitroaromatic-based compounds, 23 applications in energy conversion and molecular electronics, 4,5 catalysis, 24 and charge mobility. 25,26 Thin films of PAHs have been explored in several surfaces (Al 2 O 3 , Au(111), Si(111) and Si (100), Cu(111), graphite, Ag(111), Ge(001), and Ge(111), nanoporous gold, an alloy of gold/ silver(Au/Ag), titanium dioxide, and graphene nanosheets) to study the morphology, structure, and stability of thin films to applications in materials science and engineering.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, PAHs have been explored in applications such as nano-sensors of oxygen, detection of nitroaromatic-based compounds, applications in energy conversion and molecular electronics, , catalysis, and charge mobility. , Thin films of PAHs have been explored in several surfaces (Al 2 O 3 , Au(111), Si(111) and Si(100), Cu(111), graphite, Ag(111), Ge(001), and Ge(111), nanoporous gold, an alloy of gold/silver(Au/Ag), titanium dioxide, and graphene nanosheets) to study the morphology, structure, and stability of thin films to applications in materials science and engineering. − …”

Section: Introductionmentioning

confidence: 99%

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On the Aromatic Stabilization of Fused Polycyclic Aromatic Hydrocarbons

et al. 2021

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The thermodynamic properties and band gap energies were evaluated for six ortho- and peri-fused polycyclic aromatic hydrocarbons (PAHs): triphenylene; benzo[a]pyrene; benzo[e]pyrene; perylene; benzo[ghi]perylene; coronene. The standard molar enthalpies of formation in the crystalline state and the standard molar enthalpies of sublimation were measured by high precision combustion calorimetry and Knudsen effusion methodology, respectively. The combination of the molar enthalpies of formation in the crystalline state with the respective enthalpies of sublimation was used to evaluate the energetics of the progressive peri-fusion of the aromatic moieties from triphenylene to coronene aiming to investigate the hypothetical superaromaticity character of coronene. The linear trend of the enthalpy of formation in crystalline and gaseous phases in the series (from benzo[e]pyrene to coronene) is an irrefutable indication of a non-superaromaticity character of coronene. High accurate thermodynamic properties of sublimation (volatility, enthalpy, and entropy of sublimation) were derived by the measurement of vapor pressures as a function of temperature, using a Knudsen/quartz crystal effusion methodology. Furthermore, the π-electronic conjugation of these compounds was explored by evaluation of the optical band gaps along with this series of compounds. The morphology of perylene, benzo[ghi]perylene, and coronene thin films, deposited by physical vapor deposition onto transparent conductive oxide substrates (ITO and FTO), was used to analyze the nucleation and growth mechanisms. The morphologies observed were found to be related to the cohesive energy and entropy of the bulk.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

On the Aromatic Stabilization of Fused Polycyclic Aromatic Hydrocarbons

et al. 2021

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“…Melting points of all the synthesized analogues were measured by using Stuart digital melting point apparatus. 1 H NMR spectra of the synthesized analogues of TPE were recorded at a Bruker Avance III HD 400 MHz NMR using CDCl 3 as a solvent. The structures of the synthesized TPE analogues were further confirmed by MALDI-TOF mass spectrometry.…”

Section: Discussionmentioning

confidence: 99%

“…Among the different classes, nitroaromatic compounds (NACs) are most widely used volatile compounds in various explosive formulations. 1 Nitroaromatics vapors, even at a low level, are hazardous for the human health as well as for the environment. 2 Therefore, their real-time trace detection to avert pre-planned terrorist activities is in high demand.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Tetraphenylethylene-Based Aggregation-Induced Emission Probe for Rapid Detection of Nitroaromatic Compounds in Aqueous Media

et al. 2021

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Tetraphenylethylene (TPE) can be used to construct fluorescent probes with typical aggregation-induced emission (AIE) behavior for next-generation sensing applications. McMurry coupling and Suzuki cross coupling strategies provided the desired sensor thiophene-substituted tetraphenylethylene (THTPE). The synthesized TPE analogues were characterized by NMR spectroscopy and mass spectrometry. Maximum AIE of THTPE was observed in 90% water (H2O/THF) content due to extensive formation of aggregates. The AIE properties of THTPE have been utilized for facile detection of nitroaromatic compounds (NACs) (1.0 nM) through a fluorescence quenching mechanism. A paper strip adsorbed with the AIE-based THTPE fluorophore is developed for rapid and convenient detection of NAC-based analytes. Further, interaction of THTPE with analytes is also studied via Gaussian software at the DFT/B3LYP/6-31G(d) level of theory. Interaction energy, frontier molecular orbitals (FMOs), and non-covalent interaction (NCI) analyses are studied by using the same method. Computational results revealed that nitrobenzene (NB) has the strongest interaction while 1,3-dinitrobenzene (DNB) exhibits the least interaction with the sensor molecule. These computational results clearly demonstrate good agreement with experimental data.

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“…As a part of our on-going research on the development of fluorescence sensors for sensitive detection of NACs, − fluorene-based three CPs ( CP 1 , CP 2 , and CP 3 ) were designed and successfully synthesized through the Suzuki cross coupling reaction. Some of the already reported fluorene-based chemosensors suffer from aggregation-caused quenching (ACQ) because of their planarity in their design .…”

Section: Introductionmentioning

confidence: 99%

Fluorene-Based Fluorometric and Colorimetric Conjugated Polymers for Sensitive Detection of 2,4,6-Trinitrophenol Explosive in Aqueous Medium

et al. 2021

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Nitroaromatic explosives are a class of compounds that are responsible for various health hazards and terrorist outrages. Among these, sensitive detection of 2,4,6-trinitrophenol (TNP) explosive has always been highly desirable considering public health and national security. In this regard, three fluorene-based conjugated polymers (CP 1, CP 2, and CP 3) were synthesized through the Suzuki−Miyaura coupling reaction and were found to be highly sensitive for fluorescence detection of TNP with detection limits of 3.2, 5.7, and 6.1 pM, respectively. Excellent selectivity of CPs toward TNP was attributed to their unique π-π interactions based on fluorescence studies and density functional theory (DFT) calculations. The high sensitivity of CPs to TNP was attributed to the static quenching mechanism based on the photoinduced electron transfer process and was evaluated by fluorescence, UV−visible absorption, dynamic light scattering, Job's plots, the Benesi−Hildebrand plots, and DFT calculations. CPs were also used for colorimetric and real-water sample analysis for the detection of TNP explosive. Meanwhile, sensor-coated test strips were fabricated for on-site detection of TNP, which makes them convenient solid-supported sensors.

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Benzo[ghi]perylene and coronene as ratiometric fluorescence probes for the selective sensing of nitroaromatic explosives

Cited by 25 publications

References 22 publications

On the Aromatic Stabilization of Fused Polycyclic Aromatic Hydrocarbons

On the Aromatic Stabilization of Fused Polycyclic Aromatic Hydrocarbons

Synthesis and Tetraphenylethylene-Based Aggregation-Induced Emission Probe for Rapid Detection of Nitroaromatic Compounds in Aqueous Media

Fluorene-Based Fluorometric and Colorimetric Conjugated Polymers for Sensitive Detection of 2,4,6-Trinitrophenol Explosive in Aqueous Medium

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