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Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe

Here, we introduced a novel thiourea-based rhodamine compound as a chromo-fluorogenic indicator of nerve agent Soman and its simulant diethyl chlorophosphate (DCP). The synthesized probe N-(rhodamine B)-lactam-2-(4-cyanophenyl) thiourea (RB-CT), which has a rhodamine core linked by a cyanophenyl thi...

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Autores principales: Li, Shengsong, Zheng, Yongchao, Chen, Weiqiang, Zheng, Meiling, Zheng, He, Zhang, Zhe, Cui, Yan, Zhong, Jinyi, Zhao, Chonglin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6429212/
https://www.ncbi.nlm.nih.gov/pubmed/30813539
http://dx.doi.org/10.3390/molecules24050827
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author Li, Shengsong
Zheng, Yongchao
Chen, Weiqiang
Zheng, Meiling
Zheng, He
Zhang, Zhe
Cui, Yan
Zhong, Jinyi
Zhao, Chonglin
author_facet Li, Shengsong
Zheng, Yongchao
Chen, Weiqiang
Zheng, Meiling
Zheng, He
Zhang, Zhe
Cui, Yan
Zhong, Jinyi
Zhao, Chonglin
author_sort Li, Shengsong
collection PubMed
description Here, we introduced a novel thiourea-based rhodamine compound as a chromo-fluorogenic indicator of nerve agent Soman and its simulant diethyl chlorophosphate (DCP). The synthesized probe N-(rhodamine B)-lactam-2-(4-cyanophenyl) thiourea (RB-CT), which has a rhodamine core linked by a cyanophenyl thiosemicarbazide group, enabled a rapidly and highly sensitive response to DCP with clear fluorescence and color changes. The detection limit was as low as 2 × 10(−6) M. The sensing mechanism showed that opening of the spirolactam ring following the phosphorylation of thiosemicarbazides group formed a seven-membered heterocycle adduct, according to MS analysis and TD-DFT calculations. RB-CT exhibited high detecting selectivity for DCP, among other organophosphorus compounds. Moreover, two test kits were employed and successfully used to detect real nerve agent Soman in liquid and gas phase.
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spelling pubmed-64292122019-04-15 Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe Li, Shengsong Zheng, Yongchao Chen, Weiqiang Zheng, Meiling Zheng, He Zhang, Zhe Cui, Yan Zhong, Jinyi Zhao, Chonglin Molecules Article Here, we introduced a novel thiourea-based rhodamine compound as a chromo-fluorogenic indicator of nerve agent Soman and its simulant diethyl chlorophosphate (DCP). The synthesized probe N-(rhodamine B)-lactam-2-(4-cyanophenyl) thiourea (RB-CT), which has a rhodamine core linked by a cyanophenyl thiosemicarbazide group, enabled a rapidly and highly sensitive response to DCP with clear fluorescence and color changes. The detection limit was as low as 2 × 10(−6) M. The sensing mechanism showed that opening of the spirolactam ring following the phosphorylation of thiosemicarbazides group formed a seven-membered heterocycle adduct, according to MS analysis and TD-DFT calculations. RB-CT exhibited high detecting selectivity for DCP, among other organophosphorus compounds. Moreover, two test kits were employed and successfully used to detect real nerve agent Soman in liquid and gas phase. MDPI 2019-02-26 /pmc/articles/PMC6429212/ /pubmed/30813539 http://dx.doi.org/10.3390/molecules24050827 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Li, Shengsong
Zheng, Yongchao
Chen, Weiqiang
Zheng, Meiling
Zheng, He
Zhang, Zhe
Cui, Yan
Zhong, Jinyi
Zhao, Chonglin
Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe
title Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe
title_full Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe
title_fullStr Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe
title_full_unstemmed Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe
title_short Chromo-Fluorogenic Detection of Soman and Its Simulant by Thiourea-Based Rhodamine Probe
title_sort chromo-fluorogenic detection of soman and its simulant by thiourea-based rhodamine probe
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6429212/
https://www.ncbi.nlm.nih.gov/pubmed/30813539
http://dx.doi.org/10.3390/molecules24050827
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