Synthesis of Oxadiazolones with Hydrazides: The Mechanism and the Sensing Application as Sensitive, Rapid, and Visual Fluorescent Sensors for Phosgene

Abstract

The reaction of hydrazides with triphosgene in the presence of triethylamine is a facile method to construct various oxadiazolones. Utilizing this reaction, a new class of colorimetric and fluorogenic phosgene chemosensors were developed with the BODIPY as fluorophore, five BODIPYbased hydrazides, which exhibited highly effective reactions with phosgene. The mechanism was updated. Finally, the test paper with a hydrazide was fabricated for facile, selective, and visual detection of phosgene gas.

Synthesis, Reactivity, and Properties of a Class of π-Extended BODIPY Derivatives

“…The detection limit toward GSH was determined to be 0.33 nM (LOD = 3δ/k, Figure S14). 17 In order to test the selectivity of 2b toward GSH, the fluorescent response kinetics of 2b in the presence of the same concentration of GSH, Cys, and Hcy were investigated under the identical conditions (Figure 6c). Upon addition of GSH, the fluorescence of 2b increased rapidly and reached a plateau (∼40 s, Figure 6c), while the addition of both Cys and Hcy hardly enhanced the emission intensity.…”

Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications

“…Thus, it is essential to develop facile, fast, and reliable molecular probes . In recent years, the design and synthesis of phosgene fluorescent probes have attracted extensive attention . As described above, 2g may be a good candidate to be used as a “turn-on” fluorescent probe for phosgene.…”

Fluorescent probes for the detection of chemical warfare agents

“…31). Similarly, Gangopadhyay et al functionalized anthracene with a primary amide to afford the fluorescent probe 9-AM (193). 195 The phosgene-mediated conversion of the primary amide to nitrile was rapid (o1.5 min) and afforded a substantial increase in fluorescence emission intensity at 440 nm.…”