Fluorescent Signaling Based on Sulfoxide Profluorophores: Application to the Visual Detection of the Explosive TATP

Abstract

The first visual fluorescence-based assay for the peroxide explosive triacetone triperoxide (TATP) is described. The assay is based on a conceptually new fluorescence signaling mechanism, in which nonemissive pyrenyl sulfoxide profluorophores are oxidized to visibly emissive pyrenyl sulfones. Although not without limitations, these first-generation fluorescent probes can provide a visual response to ca. 100 nmol of TATP. In addition, the success of this assay suggests the potential for broader application of aryl sulfoxides in fluorescent chemosensing.

Fluorescent Detection of 2,4‐DNT and 2,4,6‐TNT in Aqueous Media by Using Simple Water‐Soluble Pyrene Derivatives

“…Due to the high fluorescence quantum yield (up to 0.32) [18] and the ability to form stable donor-acceptor complexes with NACs, [19] pyrene derivatives are commonly used as fluorophores and/or single-molecule chemosensors for the visual detection of nitro-and some other explosives. [20,21] In addition, some pyrene-based hybrid materials, for example, films, fibers, silica microspheres, nanoparticlesa nd crystalline wafers are widely studied as potential sensory elements fort race detection systemsa nd devicesf or nitro-explosives. [14,16,22] For example, cellulose triacetate membranesw ith pyrene-1-butyric acid as fluorophore wereu sed for screening of TNT,2 ,4-DNT and hexogen (RDX) in groundwater.…”

A Dual-Emission Amphiphile /Dye Modified Mesoporous Silica as Fluorescent Sensor for the Detection of Fe3+, Cr3+and Al3+

“…[12][13][14][15] Finally, fluorescence probe can give a fast (usually less than 1 second) and selective response to analytes, which has a low concentration. These specialties of fluorescence probes can be applied to detect trace substances, such as heavy metal ions, pesticides, [16] explosives, [17][18][19] neurotoxins, endocrine disruptors and stimulant, in the environment and human body. [20,21] Furthermore, the fluorescence with a wavelength in the range of visible light can be observed by naked eyes.…”

Detection of triacetone triperoxide using temperature cycled metal‐oxide semiconductor gas sensors

“…In the field of portable and cost efficient sensors, different technologies were tested with various advantages and disadvantages. Some of them focus on detection in liquids, such as electrochemical detection , fluorescence , chemiluminescence or biosensors , and other biologically inspired systems . Unlike most other explosives the vapor pressure of TATP (6.39 Pa at 25 °C corresponding to a concentration of approximately 63 ppm), is very high and even higher than that of TNT (9.27 × 10 −4 Pa at 25 °C, ∼9 ppb) .…”