Colorimetric and Ratiometric Chemosensor for Visual Detection of Gaseous Phosgene Based on Anthracene Carboxyimide Membrane

Abstract

In this work, we reported an anthracene carboxyimide-based chemosensor (AC-Phos) for colorimetric and ratiometric fluorescence detection of highly toxic phosgene, which displayed rapid response (<5 min) toward phosgene with a high selectivity and a low detection limit (2.3 nM). Furthermore, a facile testing membrane with a polystyrene immobilizing chemosensor has been fabricated for real-time visualizing of gaseous phosgene.

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

“…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] …”

An amino-substituted 2-(2′-hydroxyphenyl)benzimidazole for the fluorescent detection of phosgene based on an ESIPT mechanism

“…Nowadays, fluorescent detection methods are well developed and widespread due to their easy manipulation, fast response, high sensitivity and selectivity, and the possibility of real-time detection. Among them, reports on the fluorescent detection of phosgene are still limited 12–14 and mainly based on: (i) twice carbamylation reactions of fluorescence probes, which employ o -phenylenediamine, 21 o -hydroxyaniline, 22 o -aminobenzyl amine, 23 catechol, 24 ethylenediamine, 25 ethanolamine 26 or other moieties 27 as reactive site; (ii) phosgene-promoted dehydration reaction of fluorescence probes, which employ oxime 28 or amide 29 as reactive site; and (iii) several other phosgene-induced reactions, including intermolecular reaction of two fluorophores, 30 intramolecular reaction of cinnamic acids, 31 ring opening reaction of benzimidazole-fused rhodamine dye 32 and Beckmann rearrangement of ketoxime 33 (Table S2 † ). However, most of these fluorescence probes are based on mechanisms of photoinduced electron transfer (PeT), intramolecular charge transfer (ICT) or aggregation-induced emission (AIE), which might be disturbed by acetylating, 21 c phosphorylating agents 21 h or oxidizing chemicals, 21 e ,27 g resulting to false response.…”

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

“…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 .…”