Issue 9, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
15 Mei 2017
Accepted
08 Jun 2017
First published
12 Jun 2017

Org. Chem. Front., 2017,4, 1719-1725

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements