BODIPY-Based Fluorescent Sensor for the Recognization of Phosgene in Solutions and in Gas Phase

Abstract

As a highly toxic and widely used chemical, phosgene has become a serious threat to humankind and public security because of its potential use by terrorists and unexpected release during industrial accidents. For this reason, it is an urgent need to develop facile, fast, and selective detection methods of phosgene. In this Article, we have constructed a highly selective fluorescent sensor o-Pab for phosgene with a BODIPY unit as a fluorophore and o-phenylenediamine as a reactive site. The sensor o-Pab exhibits rapid response (∼15 s) in both colorimetric and turn-on fluorescence modes, high selectivity for phosgene over nerve agent mimics and various acyl chlorides and a low detection limit (2.7 nM) in solutions. In contrast to most undistinguishable sensors reported, o-Pab can react with phosgene but not with its substitutes, triphosgene and biphosgene. The excellent discrimination of o-Pab has been demonstrated to be due to the difference in highly reactive and bifunctional phosgene relative to its substitutes. Furthermore, a facile testing paper has been fabricated with poly(ethylene oxide) immobilizing o-Pab on a filter paper for real-time selective monitoring of phosgene in gaseous phase.

Blue-Emitting BODIPY Dyes

“…In the same year, Song and co-workers reported a similar approach using orthophenylenediamine (OPD)-introduced BODIPY for phosgene sensing (o-Pab, Figure 6) [38]. Unlike the ethylenediamine-substituted fluorescent probe as described above (8-EDAB), o-Pab shows no fluorescence in sensing media (chloroform, 1% triethylamine) due to photoinduced electron transfer (PET) quenching [39] from OPD to the BODIPY core and rotational deactivation along the aryl-amine-aryl single bonds.…”

Derivatization and rapid GC-MS screening of chlorides relevant to the Chemical Weapons Convention in organic liquid samples

“…For these reasons on-site methods using sensors and probes to detect phosgene in air have continuously been developed. [18][19][20][21][22][23][24] Due to the instability of phosgene in air it has been collected in impingers and sorbent tubes containing a reagent to derivatize phosgene to a stable chemical. 25 Chemical reactions of phosgene are similar to those of acid chlorides and it reacts easily with alcohols.…”

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

“…The development of portable test strips for real time sensing has made this method all the more attractive and given it an edge over other sensing methods targeted toward phosgene. It is no surprise thus that a plethora of fluorescent chemodosimetric sensors for phosgene exist many of which have utilized the phosgene mediated acylation of amines . 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.…”