Open AccessRational Design of an ICT-Based Chemodosimeter with Aggregation-Induced Emission for Colorimetric and Ratiometric Fluorescent Detection of Cyanide in a Wide pH Range
Author(s) -
Sachin D. Padghan,
Li-Ching Wang,
Wei-Kai Lin,
Jiun-Wei Hu,
Wen-Ching Liu,
KewYu Chen
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.0c05409
Subject(s) - cyanide , fluorescence , chemistry , intramolecular force , photochemistry , titration , naked eye , absorption (acoustics) , alkoxy group , nucleophilic addition , aqueous solution , inorganic chemistry , detection limit , organic chemistry , materials science , chromatography , optics , catalysis , alkyl , composite material , physics
An alkoxy-substituted 1,3-indanedione-based chemodosimeter 1 with an aggregation-induced emission (AIE) characteristic was rationally designed and synthesized for the ultrasensitive and selective sensing of cyanide in a wide pH range of 3.0-12.0. The nucleophilic addition of cyanide to the β-conjugated carbon of the 1,3-indanedione group obstructs intramolecular charge transfer (ICT) and causes a significant change in the absorption and fluorescence spectra, enabling colorimetric and ratiometric fluorescent detection of cyanide in a 90% aqueous solution. The cyanide-sensing mechanism is supported by single-crystal X-ray diffraction analysis, time-dependent density functional theory (TD-DFT) calculations, and 1 H NMR titration experiments. Sensor 1 exhibits strong yellow fluorescence in the solid state due to the AIE effect, and the paper probes containing 1 can be conveniently used to sense cyanide by the naked eye. Furthermore, chemodosimeter 1 was successfully used for sensing cyanide in real environmental water samples.