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Issue 9, 2017
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A benzothiadiazole-based fluorescent sensor for selective detection of oxalyl chloride and phosgene

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Abstract

Oxalyl chloride and phosgene are highly toxic chemicals but are widely used in industrial processes, which have been regarded as a serious threat to our health and public security. Thus, it is imperative to develop a convenient and reliable detection method for these noxious agents. In this research, we report the rational design of a fluorescent sensor (denoted as BTA) for simultaneously detecting oxalyl chloride and phosgene, in which o-phenylenediamine (OPD) as the reactive recognition site and benzothiadiazole (BTD) as the fluorophore moiety are coupled into one single benzo-fused motif. The probe works in a “turn-on” fluorescence mode due to the formation of piperazine-2,3-dione and 2-imidazolidinone rings by intramolecular cyclization reactions between the OPD part with oxalyl chloride and phosgene, respectively, which greatly inhibits the intramolecular charge transfer (ICT) process from two amines to the BTD core in the sensor BTA. The detection limit of oxalyl chloride and phosgene is as low as 3 nM and 20 nM in solutions, respectively. Moreover, the sensor exhibits outstanding selectivity toward oxalyl chloride and phosgene over the nerve-agent mimic diethyl chlorophosphate and various acyl chlorides. Furthermore, a portable test paper with BTA has been facilely fabricated for visual on-site detection of the two toxic chemicals in the gas phase.

Graphical abstract: A benzothiadiazole-based fluorescent sensor for selective detection of oxalyl chloride and phosgene

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Publication details

The article was received on 15 May 2017, accepted on 08 Jun 2017 and first published on 12 Jun 2017


Article type: Research Article
DOI: 10.1039/C7QO00378A
Citation: Org. Chem. Front., 2017,4, 1719-1725
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    A benzothiadiazole-based fluorescent sensor for selective detection of oxalyl chloride and phosgene

    W. Zhang, K. Cheng, X. Yang, Q. Li, H. Zhang, Z. Ma, H. Lu, H. Wu and X. Wang, Org. Chem. Front., 2017, 4, 1719
    DOI: 10.1039/C7QO00378A

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