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A new phenothiazine-based selective visual and fluorescent sensor for cyanide

A new donor-π-acceptor derived from phenothiazine, namely 2-(2-((10-hexyl-10H-phenothiazin-3-yl)methylene)-3-oxo-2,3-dihydroinden-1-ylidene) malononitrile (PTZON) was synthesized and fully characterized, and its potential as a fluorescent sensor for cyanide anion was investigated. The PTZON showed a...

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Autores principales: Al-Zahrani, Fatimah A. M., El-Shishtawy, Reda M., Asiri, Abdullah M., Al-Soliemy, Amerah M., Mellah, Khloud Abu, Ahmed, Nahed S. E., Jedidi, Abdesslem
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer International Publishing 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6945606/
https://www.ncbi.nlm.nih.gov/pubmed/31922151
http://dx.doi.org/10.1186/s13065-019-0656-x
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author Al-Zahrani, Fatimah A. M.
El-Shishtawy, Reda M.
Asiri, Abdullah M.
Al-Soliemy, Amerah M.
Mellah, Khloud Abu
Ahmed, Nahed S. E.
Jedidi, Abdesslem
author_facet Al-Zahrani, Fatimah A. M.
El-Shishtawy, Reda M.
Asiri, Abdullah M.
Al-Soliemy, Amerah M.
Mellah, Khloud Abu
Ahmed, Nahed S. E.
Jedidi, Abdesslem
author_sort Al-Zahrani, Fatimah A. M.
collection PubMed
description A new donor-π-acceptor derived from phenothiazine, namely 2-(2-((10-hexyl-10H-phenothiazin-3-yl)methylene)-3-oxo-2,3-dihydroinden-1-ylidene) malononitrile (PTZON) was synthesized and fully characterized, and its potential as a fluorescent sensor for cyanide anion was investigated. The PTZON showed a visible absorption band at 564 nm corresponds to an intramolecular charge transfer (ICT) and an emission band at 589 nm in CH(3)CN/H(2)O. The results of cyanide anion titration revealed ratiometric changes in both absorption and fluorescence spectra as a result of the nucleophilic addition of cyanide anion via Michael addition. The optical studies, FT-IR spectra, NMR, high-resolution mass, and DFT calculations confirmed the sensing mechanism. The selectivity of PTZON as a cyanide anion fluorescent sensor was proved in mixed solvent solutions, and the sensitivity was as low as 0.011 µM, which is far lower than the value allowed by the United States Environmental Protection Agency for drinking water (1.9 µM). Also, the detection limit of PTZON was assessed to be 3.39 μM by the spectrophotometric method. The binding stoichiometry between PTZON and cyanide anion was found to be 1:1 as evidenced by mass spectra. TLC silica-coated plates test strips demonstrated the fluorescent detection of cyanide anion.
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spelling pubmed-69456062020-01-09 A new phenothiazine-based selective visual and fluorescent sensor for cyanide Al-Zahrani, Fatimah A. M. El-Shishtawy, Reda M. Asiri, Abdullah M. Al-Soliemy, Amerah M. Mellah, Khloud Abu Ahmed, Nahed S. E. Jedidi, Abdesslem BMC Chem Research Article A new donor-π-acceptor derived from phenothiazine, namely 2-(2-((10-hexyl-10H-phenothiazin-3-yl)methylene)-3-oxo-2,3-dihydroinden-1-ylidene) malononitrile (PTZON) was synthesized and fully characterized, and its potential as a fluorescent sensor for cyanide anion was investigated. The PTZON showed a visible absorption band at 564 nm corresponds to an intramolecular charge transfer (ICT) and an emission band at 589 nm in CH(3)CN/H(2)O. The results of cyanide anion titration revealed ratiometric changes in both absorption and fluorescence spectra as a result of the nucleophilic addition of cyanide anion via Michael addition. The optical studies, FT-IR spectra, NMR, high-resolution mass, and DFT calculations confirmed the sensing mechanism. The selectivity of PTZON as a cyanide anion fluorescent sensor was proved in mixed solvent solutions, and the sensitivity was as low as 0.011 µM, which is far lower than the value allowed by the United States Environmental Protection Agency for drinking water (1.9 µM). Also, the detection limit of PTZON was assessed to be 3.39 μM by the spectrophotometric method. The binding stoichiometry between PTZON and cyanide anion was found to be 1:1 as evidenced by mass spectra. TLC silica-coated plates test strips demonstrated the fluorescent detection of cyanide anion. Springer International Publishing 2020-01-07 /pmc/articles/PMC6945606/ /pubmed/31922151 http://dx.doi.org/10.1186/s13065-019-0656-x Text en © The Author(s) 2020 Open AccessThis article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article's Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article's Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated in a credit line to the data.
spellingShingle Research Article
Al-Zahrani, Fatimah A. M.
El-Shishtawy, Reda M.
Asiri, Abdullah M.
Al-Soliemy, Amerah M.
Mellah, Khloud Abu
Ahmed, Nahed S. E.
Jedidi, Abdesslem
A new phenothiazine-based selective visual and fluorescent sensor for cyanide
title A new phenothiazine-based selective visual and fluorescent sensor for cyanide
title_full A new phenothiazine-based selective visual and fluorescent sensor for cyanide
title_fullStr A new phenothiazine-based selective visual and fluorescent sensor for cyanide
title_full_unstemmed A new phenothiazine-based selective visual and fluorescent sensor for cyanide
title_short A new phenothiazine-based selective visual and fluorescent sensor for cyanide
title_sort new phenothiazine-based selective visual and fluorescent sensor for cyanide
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6945606/
https://www.ncbi.nlm.nih.gov/pubmed/31922151
http://dx.doi.org/10.1186/s13065-019-0656-x
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