An amino-substituted 2-(2′-hydroxyphenyl)benzimidazole for the fluorescent detection of phosgene based on an ESIPT mechanism

Abstract

An easily prepared phosgene probe, 5′-amino-2-(2′-hydroxyphenyl)benzimidazole (P1), is designed and studied. Based on ESIPT mechanism, P1 exhibits ratiometric, sensitive and selective detection of phosgene both in solution and gas phase.

Fluorescent probes for the detection of chemical warfare agents

“…Li et al reported the ESIPT-based fluorescent probe, P1 ( 185 ), for phosgene detection. 191 The hydroxyl and imidazole groups of 185 reacted with phosgene to form a six-membered ring product. Due to the inhibition of ESIPT, a ratiometric fluorescence response was observed in CH 2 Cl 2 with a decrease in fluorescence emission at 540 nm and increase at 358 nm, displaying a LOD of 5.3 nM.…”

Synthesis and characterization of dicarboxamide derivative: Cu+2 selective turn‐on fluorometric and colorimetric chemosensor

“…Considering the UV spectra, when Compound 3 was excited at 355 nm, emission of 3 was determined with a large Stokes' shift (191 nm) at 546 nm in the fluorescence spectrum (see Figure 1A). Molecules bearing 2-(2 0 -Hydroxyphenyl) benzothiazole (HBT), 2-(2 0 -Hydroxyphenyl) benzoxazole (HBO), 2-(2 0 -Hydroxyphenyl) benzimidazole or 2-(2 0 -Aminophenyl) benzimidazole (APBI) moiety exhibit ESIPT [31][32][33], AIE [34], ICT [35], and PCET [36] process, and they have been applied to detect various analytes. At first, we explored different solvent effect on the absorption and fluorescence feature of Compound 3 to evaluate AIE phenomena.…”

ESIPT-PET based triphenylamine-anthraquinone probe for the detection of phosgene: DFT studies, real-time application in soil samples and test strips

“…For the detection of phosgene, a small number of probes with ESIPT-like behaviours have also been created. [44][45][46] These probes are depicted in Table 1. This gave rise to the concept of an ESIPT probe with a triphenylamine core structure.…”