Ratiometric Fluorescent/Colorimetric Cyanide-Selective Sensor Based on Excited-State Intramolecular Charge Transfer−Excited-State Intramolecular Proton Transfer Switching

A novel salicylideneaniline-based fluorescent sensor, SB1, with a unique excited-state intramolecular charge transfer–excited-state intramolecular proton transfer (ESICT–ESIPT) coupled system was synthesized and demonstrated to fluorescently sense CN– with specific selectivity and high sensitivity i...

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Bibliographic Details
Published in:Analytical chemistry (Washington) 2014-05, Vol.86 (10), p.4648-4652
Main Authors: Lin, Wei-Chi, Fang, Sin-Kai, Hu, Jiun-Wei, Tsai, Hsing-Yang, Chen, Kew-Yu
Format: Article
Language:English
Subjects:
Analytical chemistry
Aqueous solutions
Biosensors
Charge
Charge transfer
Chemical compounds
Colorimetry
Cyanides - analysis
Excitation
Fluorescence
Fluorescent Dyes
Joining
Protons
Sensors
Spectrometry, Fluorescence
Switching
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Summary:A novel salicylideneaniline-based fluorescent sensor, SB1, with a unique excited-state intramolecular charge transfer–excited-state intramolecular proton transfer (ESICT–ESIPT) coupled system was synthesized and demonstrated to fluorescently sense CN– with specific selectivity and high sensitivity in aqueous media based on ESICT–ESIPT switching. A large blue shift (96 nm) was also observed in the absorption spectra in response to CN–. The bleaching of the color could be clearly observed by the naked eye. Moreover, SB1-based test strips were easily fabricated and low-cost, and could be used in practical and efficient CN– test kits. Density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations further support the cyanide-induced ESICT–ESIPT switching mechanism. The results provide the proof of concept that the colorimetric and ratiometric fluorescent cyanide-selective chemodosimeter can be created based on an ESICT–ESIPT coupled system.
ISSN:0003-2700
1520-6882
DOI:10.1021/ac501024d