Construction of a ratiometric phosgene probe by chromophore formation from auxochrome

Abstract

A new fluorescent probe for ratiometric detection of phosgene is reported. This probe was constructed with classic 1,8-naphthalimide and 2-(2-aminophenyl)benzimidazole by Ullmann coupling reaction. After exposure to phosgene, yellow fluorescence weakened while blue fluorescence enhanced significantly. There was a ratiometric response between 542 nm and 490 nm. The detection limit (LOD) was 6.7 nM and the response time was within 200 s in CHCl3. Meaningfully, a new chromophore, benzo [4,5]imidazo[1,2-c]quinazolin-6(5H)-one, was formed after 2-(2-aminophenyl)benzimidazole unit reacted with phosgene, and the ratiometric response was achieved by two chromophores in which the mechanism was confirmed by 1H NMR spectra, HRMS and theoretical calculation. Furthermore, test papers and nanofibers were fabricated with the probe, which could sensitive detection of phosgene within 10 min and 1 min respectively.