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一种新型的基于吩噻嗪的氰化物选择性视觉和荧光传感器。

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

作者信息

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

机构信息

1Chemistry Department, Faculty of Science, King Khalid University, P.O.Box 9004, Abha, 61413 Saudi Arabia.

2Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589 Saudi Arabia.

出版信息

BMC Chem. 2020 Jan 7;14(1):2. doi: 10.1186/s13065-019-0656-x. eCollection 2020 Dec.

DOI:10.1186/s13065-019-0656-x
PMID:31922151
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6945606/
Abstract

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 CHCN/HO. 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.

摘要

合成并全面表征了一种源自吩噻嗪的新型供体-π-受体，即2-(2-((10-己基-10H-吩噻嗪-3-基)亚甲基)-3-氧代-2,3-二氢茚-1-亚基)丙二腈(PTZON)，并研究了其作为氰化物阴离子荧光传感器的潜力。PTZON在564 nm处有一个可见吸收带，对应分子内电荷转移(ICT)，在CHCN/HO中于589 nm处有一个发射带。氰化物阴离子滴定结果表明，由于氰化物阴离子通过迈克尔加成进行亲核加成，吸收光谱和荧光光谱均发生了比例变化。光学研究、傅里叶变换红外光谱、核磁共振、高分辨率质谱和密度泛函理论计算证实了传感机制。在混合溶剂溶液中证明了PTZON作为氰化物阴离子荧光传感器的选择性，其灵敏度低至0.011 μM，远低于美国环境保护局规定的饮用水允许值(1.9 μM)。此外，通过分光光度法评估PTZON的检测限为3.39 μM。质谱表明PTZON与氰化物阴离子之间的结合化学计量比为1:1。硅胶板薄层层析测试条展示了对氰化物阴离子的荧光检测。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/fa596d6dd4cf/13065_2019_656_Fig15_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/ec2b51f76f4f/13065_2019_656_Sch1_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/2591548944e5/13065_2019_656_Fig2_HTML.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/b6800ec15215/13065_2019_656_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/cb6c04d16636/13065_2019_656_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/5de0d21a1ab9/13065_2019_656_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/c4b0adcac957/13065_2019_656_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/661c1ca30bac/13065_2019_656_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/890f81ea07cd/13065_2019_656_Fig12_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/2f737440f71c/13065_2019_656_Fig13_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/771b67c1aba1/13065_2019_656_Fig14_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/fa596d6dd4cf/13065_2019_656_Fig15_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/ec2b51f76f4f/13065_2019_656_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/58833512dda8/13065_2019_656_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/2591548944e5/13065_2019_656_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/19486b15b789/13065_2019_656_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/69778ddeff35/13065_2019_656_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/b718ee858833/13065_2019_656_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/f172b0ae5880/13065_2019_656_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/b6800ec15215/13065_2019_656_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/cb6c04d16636/13065_2019_656_Fig8_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/5de0d21a1ab9/13065_2019_656_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/c4b0adcac957/13065_2019_656_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/661c1ca30bac/13065_2019_656_Fig11_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/890f81ea07cd/13065_2019_656_Fig12_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/2f737440f71c/13065_2019_656_Fig13_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/771b67c1aba1/13065_2019_656_Fig14_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c9f3/6945606/fa596d6dd4cf/13065_2019_656_Fig15_HTML.jpg

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