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用作pH值和氟离子颜色指示剂的羟基查耳酮染料。

Hydroxychalcone dyes that serve as color indicators for pH and fluoride ions.

作者信息

Du Yanqing, Liang Fengying, Hu Mixia, Bu Ren, Wang Meiling, Tsuda Akihiko, Eerdun Chaolu

机构信息

Department of Pharmaceutical Sciences, Inner Mongolia Medical University Jinshan Economic & Technology Development District Hohhot Inner Mongolia 010110 China

Department of Chemistry, Graduate School of Science, Kobe University 1-1 Rokkodai-cho, Nada-ku Kobe 657-8501 Japan

出版信息

RSC Adv. 2020 Oct 12;10(61):37463-37472. doi: 10.1039/d0ra06719a. eCollection 2020 Oct 7.

DOI:10.1039/d0ra06719a
PMID:35521233
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9057117/
Abstract

A chalcone, which is composed of two aromatic rings bridged by an α,β-unsaturated carbonyl group, exhibits a variety of biological activities. With an objective to develop a novel chalcone-based functional dye, we have synthesized a chalcone diol CLN1, bearing two OH groups at the 2-positions on both phenyl rings, as well as reference compounds CLN2-6, and found that it serves as color indicators for pH and fluoride ions. CLN1 showed a vivid color change from colorless to yellow (halochromism) in water at pH ≥ 10. Furthermore, it presented a selective color change from colorless to red upon the addition of TBAF in an organic solvent such as CHCN. CLN1 provided a strong red-shifted absorption band in the visible region under alkaline conditions in water and upon the addition of TBAF in CHCN. The absorption spectral study together with TD-DFT calculations and X-ray crystallographic analysis revealed that the characteristic π-resonant structures of CLN1 caused by the ionization or OH-F interactions and the planar conformation due to its intramolecular hydrogen bonding may provide a strong charge transfer (CT) absorption in the visible region.

摘要

查尔酮由两个通过α,β-不饱和羰基桥连的芳环组成，具有多种生物活性。为了开发一种新型的基于查尔酮的功能染料，我们合成了一种查尔酮二醇CLN1，其在两个苯环的2-位带有两个羟基，以及参考化合物CLN2-6，并发现它可作为pH和氟离子的颜色指示剂。CLN1在pH≥10的水中呈现从无色到黄色的鲜明颜色变化（加酸显色）。此外，在诸如CHCN的有机溶剂中加入TBAF后，它呈现从无色到红色的选择性颜色变化。CLN1在水中碱性条件下以及在CHCN中加入TBAF后，在可见光区域提供了一个强烈红移的吸收带。吸收光谱研究结合TD-DFT计算和X射线晶体学分析表明，由电离或OH-F相互作用引起的CLN1的特征π共振结构以及由于其分子内氢键导致的平面构象可能在可见光区域提供强烈的电荷转移（CT）吸收。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/a38fb10ebadc/d0ra06719a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/4a8c325a434f/d0ra06719a-c1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/10d6d1930e30/d0ra06719a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/93413e7494e2/d0ra06719a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/54ab70b51957/d0ra06719a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/e9ba032390d7/d0ra06719a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/2c87bef5e7ce/d0ra06719a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/02e703d7fa75/d0ra06719a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/dfcff66b1658/d0ra06719a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/a38fb10ebadc/d0ra06719a-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/4a8c325a434f/d0ra06719a-c1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/10d6d1930e30/d0ra06719a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/93413e7494e2/d0ra06719a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/54ab70b51957/d0ra06719a-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/e9ba032390d7/d0ra06719a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/2c87bef5e7ce/d0ra06719a-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/02e703d7fa75/d0ra06719a-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/dfcff66b1658/d0ra06719a-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/52f6/9057117/a38fb10ebadc/d0ra06719a-f6.jpg

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2
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Inorg Chem. 2017 Oct 2;56(19):11577-11590. doi: 10.1021/acs.inorgchem.7b01304. Epub 2017 Sep 19.
3
Chalcone: A Privileged Structure in Medicinal Chemistry.
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Chem Rev. 2017 Jun 28;117(12):7762-7810. doi: 10.1021/acs.chemrev.7b00020. Epub 2017 May 10.
4
Diverse Molecular Targets for Chalcones with Varied Bioactivities.具有多种生物活性的查耳酮的不同分子靶点。
Med Chem (Los Angeles). 2015 Aug;5(8):388-404. doi: 10.4172/2161-0444.1000291. Epub 2015 Aug 22.
5
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J Enzyme Inhib Med Chem. 2016;31(1):23-30. doi: 10.3109/14756366.2014.1003215. Epub 2015 Feb 16.
6
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7
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8
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