Highly Selective and Sensitive Colorimetric and Fluorescent Chemosensors for Rapid Detection of Cyanide Anions in Aqueous Medium: Investigation on Supramolecular Recognition of Tweezer‑shaped Salophenes

Three tweezer‑shaped salophenes having catechols ( 1 ), phenols ( 2 ) and anisoles ( 3 ) units in conjunction to the dipodal Schiff bases have been applied for the optical sensing of cyanide (CN¯) ions in CH 3 CN-H 2 O (7:3) as solvent of choice. Among them, compounds 1 and 2 recognized CN¯, relying...

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Bibliographic Details
Published in:Journal of fluorescence Vol. 31; no. 4; pp. 1085 - 1097
Main Authors: Darabi, Hossein Reza, Nazarian, Ramo, Alizadeh, Sepideh, Aghapoor, Kioumars, Ebadinia, Leila
Format: Journal Article
Language:English
Published: New York Springer US 01.07.2021
Springer Nature B.V
Subjects:
Analytical Chemistry
Anions
Anions - analysis
Aqueous solutions
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Chemical sensors
Chemoreceptors
Colorimetry
Colorimetry - methods
Cyanides - analysis
Fluorescence
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Hydroxyl groups
Imines
Molecular Structure
NMR spectroscopy
Original Article
Phenols
Recognition
Salicylates - analysis
Salicylates - chemistry
Schiff Bases - chemistry
Selectivity
Spectrometry, Fluorescence
Water - chemistry
Schiff base
Salophenes
Cyanide sensing
IACC process
Test kits
ISSN:1053-0509, 1573-4994, 1573-4994
Online Access:Get full text
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Summary:Three tweezer‑shaped salophenes having catechols ( 1 ), phenols ( 2 ) and anisoles ( 3 ) units in conjunction to the dipodal Schiff bases have been applied for the optical sensing of cyanide (CN¯) ions in CH 3 CN-H 2 O (7:3) as solvent of choice. Among them, compounds 1 and 2 recognized CN¯, relying on distinct color and spectral changes. They are easy-to-use probes that exhibit extremely high sensitivity (limit of detection = 1–10 nM), rapid response (5 s) and excellent selectivity. Moreover, the visual detection and concentration determination of CN¯ by solution test kits of both sensors are the advantages for the practical applications. Based on the fluorescence and NMR spectroscopy, as well as the OH¯ and reversibility experiments, the explicit effect of hydroxyl groups on sensing and as well the different recognition of 1 and 2 toward CN¯ ions was proved. While probe 1 senses CN¯ via deprotonation, probe 2 recognizes it through an intramolecular aldimine condensation cyclization, leading to formation of anions of dihydroxyquinoxaline 4 . This chemodosimetry is being reported for the first time in a Schiff’s base. Furthermore, the similarity of fluorescence and NMR responses of 2 and 4 toward CN¯ supports the proposed process.
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ISSN:1053-0509
1573-4994
1573-4994
DOI:10.1007/s10895-021-02738-9