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Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol

Abstract

4-(4-Nitrobenzylideneamine)phenol was used in two strategies allowing the highly selective detection of F{sup -} and CN{sup -}. Firstly, the compound in acetonitrile acts as a chromogenic chemosensor based on the idea that more basic anions cause its deprotonation (colorless solution), generating a colored solution containing phenolate. The discrimination of CN{sup -} over F{sup -} was obtained by adding 1.4% water to acetonitrile: water preferentially solvates F{sup -}, leaving the CN{sup -} free to deprotonate the compound. Another strategy involved an assay comprised of the competition between phenolate dye and the analyte for calyx[4]pyrrole in acetonitrile, a receptor highly selective for F{sup -}. Phenolate and calyx[4]pyrrole form a hydrogen-bonded complex, which changes the color of the medium. On the addition of various anions, only F{sup -} was able to restore the original color corresponding to phenolate in solution due to the fact that the anion dislodges phenolate from the complexation site. (author)
Authors:
Nicoleti, Celso R; Marini, Vanderleia G; Zimmermann, Lizandra M; Machado, Vanderlei G., E-mail: vanderlei.machado@ufsc.br [1] 
  1. Departamento de Quimica, Universidade Federal de Santa Catarina (UFSC), Florianopolis, SC (Brazil)
Publication Date:
Aug 15, 2012
Product Type:
Journal Article
Resource Relation:
Journal Name: Journal of the Brazilian Chemical Society; Journal Volume: 23; Journal Issue: 8
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; ACETONITRILE; BENZALDEHYDE; BUTYL RADICALS; CHEMICAL SHIFT; CYANIDES; ETHANOL; HYDROGEN 1; INFRARED SPECTRA; NMR SPECTRA; PH VALUE; PHENOLATES; PYRROLES; STOICHIOMETRY; TEMPERATURE DEPENDENCE; TITRATION; ULTRAVIOLET SPECTRA
OSTI ID:
22028861
Country of Origin:
Brazil
Language:
English
Other Identifying Numbers:
Journal ID: ISSN 0103-5053; CODEN: JOCSET; TRN: BR12V3049116990
Availability:
Available from http://www.scielo.br/pdf/jbchs/v23n8/aop055_12.pdf
Submitting Site:
BRN
Size:
page(s) 1488-1500
Announcement Date:
Jan 31, 2013

Citation Formats

Nicoleti, Celso R, Marini, Vanderleia G, Zimmermann, Lizandra M, and Machado, Vanderlei G., E-mail: vanderlei.machado@ufsc.br. Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol. Brazil: N. p., 2012. Web. doi:10.1590/S0103-50532012005000007.
Nicoleti, Celso R, Marini, Vanderleia G, Zimmermann, Lizandra M, & Machado, Vanderlei G., E-mail: vanderlei.machado@ufsc.br. Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol. Brazil. https://doi.org/10.1590/S0103-50532012005000007
Nicoleti, Celso R, Marini, Vanderleia G, Zimmermann, Lizandra M, and Machado, Vanderlei G., E-mail: vanderlei.machado@ufsc.br. 2012. "Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol." Brazil. https://doi.org/10.1590/S0103-50532012005000007.
@misc{etde_22028861,
title = {Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol}
author = {Nicoleti, Celso R, Marini, Vanderleia G, Zimmermann, Lizandra M, and Machado, Vanderlei G., E-mail: vanderlei.machado@ufsc.br}
abstractNote = {4-(4-Nitrobenzylideneamine)phenol was used in two strategies allowing the highly selective detection of F{sup -} and CN{sup -}. Firstly, the compound in acetonitrile acts as a chromogenic chemosensor based on the idea that more basic anions cause its deprotonation (colorless solution), generating a colored solution containing phenolate. The discrimination of CN{sup -} over F{sup -} was obtained by adding 1.4% water to acetonitrile: water preferentially solvates F{sup -}, leaving the CN{sup -} free to deprotonate the compound. Another strategy involved an assay comprised of the competition between phenolate dye and the analyte for calyx[4]pyrrole in acetonitrile, a receptor highly selective for F{sup -}. Phenolate and calyx[4]pyrrole form a hydrogen-bonded complex, which changes the color of the medium. On the addition of various anions, only F{sup -} was able to restore the original color corresponding to phenolate in solution due to the fact that the anion dislodges phenolate from the complexation site. (author)}
doi = {10.1590/S0103-50532012005000007}
journal = []
issue = {8}
volume = {23}
journal type = {AC}
place = {Brazil}
year = {2012}
month = {Aug}
}