“On–off” fluorescence detection of exposed phosgene via pyrazine ring formation on a triphenyl amine backbone supplemented with a theoretical approach and practical environmental applications

Abstract

Using 4-(diphenylamino)benzaldehyde as the fluorophore and 2,3-diaminomaleonitrile, a fluorescent probe known as 2-amino-3-(((E)-4-(diphenylamino)benzylidene)amino)-maleonitrile (ADM) has been developed for the selective detection of phosgene through a unique cyclization pathway producing a substituted pyrazine derivative attached to a triphenyl amine backbone. This reaction led to a notable reduction in the emission intensity of ADM at 565 nm. This is the first study that reports ADM as a sensory material for the selective detection of phosgene, achieved by forming a new heterocyclic pyrazine structure. With a quick response time of only 80 seconds, the detection limit of the probe ADM towards phosgene has been calculated as 4.23 μM. Several spectroscopic methods, including UV-vis, emission spectroscopy, mass spectrometry, and computational investigations are used to study the sensing behavior. In practical applications, the sensor ADM can be used for soil analysis, the dipstick method, and the detection of phosgene from chlorinated hydrocarbon sources such as dichloromethane, chloroform and household solvents like paint remover.