An ultrasensitive fluorescent probe for phosgene detection in solution and in air

Bai, Luoyi; Feng, Weiyong; Feng, Guoqiang

doi:10.1016/j.dyepig.2018.12.013

Cited by 64 publications

(27 citation statements)

References 34 publications

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“…Due to their low cost, specificity, high sensitivity, and ease of use, many fluorescent probes for phosgene have been reported [5] with two nucleophilic groups as the active site for the reaction, o ‐diamine (including one amine plus one o ‐aromatic nitrogen), [6a–y] one amine plus one o ‐hydroxy group, [7a–c] o ‐dihydroxy [8] group and others, [9a–l] and summarized in Table S1 in the Supporting Information. Among the largest class of probes, with o ‐phenylenediamine as the active site, would produce a similar fluorescence response to nitric oxide (NO), [6e, f] which induces o ‐phenylenediamine to form benzotriazole [10] …”

Section: Introductionmentioning

confidence: 99%

Sensitive and Visual Detection of Phosgene by a TICT‐Based BODIPY Dye with 8‐(o‐Hydroxy)aniline as the Active Site

Chong

et al. 2021

Chemistry A European J

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Phosgene and its substitutes (diphosgene and triphosgene) are widely utilized as chemical industrial materials and chemical warfare agents and pose a threat to public health and environmental safety due to their extreme toxicity. Research efforts have been directed to develop selective and sensitive detection methods for phosgene and its substitutes. In this paper, we have prepared two BODIPY‐based fluorescent probes, o‐Pah and o‐Pha, which are two isomers with different active sites, ortho‐aminohydroxy (3′,4′ or 4′,3′) phenyls at meso position of BODIPY, and compared their sensing performance toward triphosgene. The probe with o‐(4′‐amino‐3′‐hydroxyl), o‐Pha, exhibits better sensing performance over the o‐(3′‐amino‐4′‐hydroxyl), o‐Pah, for instance, a lower limit of detection (LOD) (0.34 nm vs. 1.2 nm), and more rapid response (10 s vs. 200 s). Furthermore, based on the above comparative studies, a red‐fluorescence probe o‐Phae has been constructed through extending 3,5‐conjugation of o‐Pha. The probe o‐Phae displays rapid response (60 s), high sensitivity to triphosgene (LOD=0.88 nm), and high selectivity for triphosgene over relevant analytes including nitric oxide. Finally, a facile test strip for phosgene was fabricated by immobilizing o‐Phae in a polyethylene oxide membrane for sensitive (<2 ppm) and selective detection of phosgene in the gas phase.

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Section: Introductionmentioning

confidence: 99%

Sensitive and Visual Detection of Phosgene by a TICT‐Based BODIPY Dye with 8‐(o‐Hydroxy)aniline as the Active Site

Chong

et al. 2021

Chemistry A European J

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“…However, little attention has been devoted to this process. Up to now, there are only two AIE sensors based on tetraphenylethene 23 and 2-(2′-hydroxyphenyl)benzothiazole 24 with low detections limits of 1.87 and 0.34 ppm for detecting phosgene in gas phase, respectively. Nevertheless, the development of AIE-based probes for sensing gaseous phosgene with high sensitivity, fast response, and noticeable color changes still remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

“…In contrast, fluorescence-based sensing systems are strikingly advantageous because of their low cost, high sensitivity, simple operation, and great convenience for field detection . Over the past years, a variety of fluorescent sensors for phosgene have been developed by utilizing different fluorophores, such as BODIYs, − coumarins, , rhodamines, , naphthalimides, − and others. − In general, the molecular design strategy mainly depends on phosgene-mediated reactions with electron-donating amine or hydroxyl groups in these sensors, resulting in the generation of electron-withdrawing carbamate, urea, or nitrile. These specific transformations typically lead to the suppression of fluorescence quenching processes, including photoinduced electron transfer (PET), − ,, intramolecular charge transfer (ICT), ,,− , or excited state intramolecular proton transfer (ESIPT). , Additionally, other sensing reactions mediated by phosgene involve the ring-opening of amino-containing spiro-(deoxy)lactam, cyclization of hydroxyl cinnamic acids, and hetero-cross-linking of amino-containing acceptor and donor fluorophores to give a FRET process …”

Section: Introductionmentioning

confidence: 99%

Selectively Light-up Detection of Phosgene with an Aggregation-Induced Emission-Based Fluorescent Sensor

Cheng

Yang

et al. 2019

ACS Omega

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Phosgene, a widely used but highly toxic substance, may pose a serious risk to public safety and health because of the potential abuse and possible accidental leakage. Consequently, it is of great significance to develop a rapid, reliable, and sensitive detection method for this noxious agent. In this work, an aggregation-induced emission-based sensor, 3,6-bis(1,2,2-triphenylvinyl)benzene-1,2-diamine (DATPE), has been rationally designed for detecting phosgene by conjugation of o-phenylenediamine (OPD) core as the reactive recognition moiety decorated with two peripheral triphenylethylene (TPE) units. A light-up fluorescence response is achieved by the fast cyclization reaction of OPD part and phosgene along with the formation of 2-imidazolidinone ring, thus inhibiting the intramolecular charge transfer quenching process in the sensor. Moreover, an easy-to-use test paper with DATPE is fabricated for onsite visual detection of phosgene in the gas phase even at a concentration of as low as 0.1 ppm.

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“…In each of these cases the acylation reaction has culminated in a measurable fluorescence spectral change through the involvement of a fluorescence signalling species such as courmarin, rhodamine, benzothiazole etc. Other functional groups have also been utilized such as oxime, ethanolamino, imino and carboxylic acid . Recently, a relatively less reactive functional group, the primary amide has been employed by Yang et al .…”

Section: Introductionmentioning

confidence: 99%

A Powerful Turn‐On Fluorescent Probe for Phosgene: A Primary Amide Strategically Attached to an Anthracene Fluorophore

2019

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We report here the application of a robust, selective primary amide moiety appended to a fluorescence signalling entity‐ anthracene, the sensing platform, 9‐AM with a view to fluorescent chemosensing of hazardous phosgene gas. The impressively fast (reaction time<1.5 min) detection of phosgene was achieved through the dehydration of the primary amide functionality to a nitrile group. A low detection limit of 5.56 nm ensures applicability of the probe for sensing of minute levels of phosgene well below prescribed safe limits. In addition, TLC sticks impregnated with the probe function as efficient gas phase phosgene sensors with real‐time applicability.

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An ultrasensitive fluorescent probe for phosgene detection in solution and in air

Cited by 64 publications

References 34 publications

Sensitive and Visual Detection of Phosgene by a TICT‐Based BODIPY Dye with 8‐(o‐Hydroxy)aniline as the Active Site

Sensitive and Visual Detection of Phosgene by a TICT‐Based BODIPY Dye with 8‐(o‐Hydroxy)aniline as the Active Site

Selectively Light-up Detection of Phosgene with an Aggregation-Induced Emission-Based Fluorescent Sensor

A Powerful Turn‐On Fluorescent Probe for Phosgene: A Primary Amide Strategically Attached to an Anthracene Fluorophore

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