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

Abstract

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.

Fluorescent probes for the detection of chemical warfare agents

“…Cheng et al developed the AIE-based fluorescent probe, DATPE ( 159 ), for phosgene detection in THF–H 2 O. 170 o -Phenylenediamine was chosen as the recognition moiety, while two peripheral triphenylethylene units were employed as the AIEgens. In the presence of phosgene, 159 formed the expected product with an increase in fluorescence emission at 496 nm.…”

ESIPT-PET based triphenylamine-anthraquinone probe for the detection of phosgene: DFT studies, real-time application in soil samples and test strips

“…Alternative methods include altering the fluorescence resonance energy transfer (FRET) by either generating the ring opening of rhodamine derivatives 44 by phosgene-induced covalent cross-linking 31 or by cyclizing a flexible chromophore precursor. 43 The specifics of these two strategies are covered in the sections that follow. For the detection of phosgene, a small number of probes with ESIPT-like behaviours have also been created.…”

“…41,42 The vast majority of fluorescent phosgene probes created and published to date employ a conventional sensing strategy. The acylation of amine-containing fluorophores, such as coumarin, 23,31 naphthalimide, 23,41 BODIPY, 36,43 rhodamine, 44 pyronin, 27 and benzothiadiazole, is required for this approach. Another illustration of this strategy is the acylation reaction.…”

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] …”