A CH-Controlled Colorimetric Probe Based on Anthracene Carboximide for Near-Infrared Cyanide Detection

Abstract

A chemical sensor that can induce near-infrared red-shifted response represents a promising strategy for the design and development of anion probes. In this work, novel CH-controlled colorimetric probe 3 based on anthracene carboximide was developed for near-infrared detection of cyanide. Probe 3 consisted of CHCN binding site to anthracene carboximide fluorophore, and showed a significant visual change from yellow-green (535 nm) to deep violet (825 nm) with a larger redshift (≈ 290 nm) and fluorescence quenching at 480 nm and 520 nm upon interacting with cyanide. Job curves determined 1:1 binding stoichiometry of probe 3 with cyanide. Additonally, probe 3 detected cyanide ion conveniently in aqueous solution and could be reused after trifluoroacetic acid treatment. Colorimetric test paper was used to detect cyanide in aqueous solutions. The C-H deprotonation sensing mechanism was confirmed by ¹H NMR titration. The near-infrared detection of cyanide by CH-controlled probes was founded for the first time.

Keywords: Anthracene carboximide; Cyanide probe; Deprotonation; Near-infrared.