A Fluorescent Chemosensor Based on Coumarin for Squential Recognition of Al3+ and Pyrophosphate (PPi) in Aqueous Solution

doi:10.6023/cjoc202010007

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1161-1167.DOI: 10.6023/cjoc202010007 Previous Articles Next Articles

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一种基于香豆素骨架的荧光化学传感器于水溶液中实现对Al³⁺和焦磷酸根(PPi)的连续识别

孟宪娇^a, 赵晋忠^a, 张永坡^a, 李志春^b, 袁长春^b^,^*(), 马文兵^b^,^*()

a 山西农业大学基础部山西晋中 030801
b 中北大学化学工程与技术学院太原 030051

收稿日期:2020-10-06 修回日期:2020-10-28 发布日期:2020-11-12
通讯作者: 袁长春, 马文兵
基金资助:
山西省基础应用研究(201801D221087); 山西农业大学科技创新(2020BQ18); 山西省优秀博士来晋工作奖励(SXYBKY2019046); 山西省高等学校创新(2020L0140)

A Fluorescent Chemosensor Based on Coumarin for Squential Recognition of Al³⁺ and Pyrophosphate (PPi) in Aqueous Solution

Xianjiao Meng^a, Jinzhong Zhao^a, Yongpo Zhang^a, Zhichun Li^b, Changchun Yuan^b^,^*(), Wenbing Ma^b^,^*()

a Basic Sciences Depart, Shanxi Agricultural University, Jinzhong, Shanxi 030801
b School of Chemical Engineering and Technology, North University of China, Taiyuan 030051

Received:2020-10-06 Revised:2020-10-28 Published:2020-11-12
Contact: Changchun Yuan, Wenbing Ma
About author:
* Corresponding authors. E-mail: mawenbing@nuc.edu.cn;
ycc870108@126.com
Supported by:
Applied Basic Research Programs of Shanxi Province(201801D221087); Science and Technology Innovation Project of Shanxi Agricultural University(2020BQ18); Shanxi Excellent Doctor Grant Award(SXYBKY2019046); Science and Technology Innovation Project of Colleges and Universities(2020L0140)

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Abstract

A novel fluorescent chemosensor (E)-N'-(3-((bis(pyridin-2-ylmethyl)amino)methyl)-2-hydroxy-5-methylbenzyl- idene)-7-(diethylamino)-2-oxo-2H-chromene-3-carbohydrazide (1) has been synthesized and showed an obviously “off-on-off” fluorescence response toward Al ³⁺ and pyrophosphate (PPi) in aqueous solution. The detection limits of sensor 1 were 0.26 μmol/L to Al ³⁺ and 0.1 μmol/L to PPi, and the binding stoichiometry was 1∶1. In addition, the binding mechanism was further confirmed by fluorescence titration, nuclear magnetic titration and ESI-MS. The effective determination pH range for Al ³⁺ and PPi was from 2 to 10, and the cycle response test could reach 4 times.

Key words: coumarin, fluorescent chemosensor, Al³⁺, PPi, sequential recognition

Cite this article

Xianjiao Meng, Jinzhong Zhao, Yongpo Zhang, Zhichun Li, Changchun Yuan, Wenbing Ma. A Fluorescent Chemosensor Based on Coumarin for Squential Recognition of Al³⁺ and Pyrophosphate (PPi) in Aqueous Solution[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1161-1167.

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Fig. & Tab. 11

Scheme 1. Synthesis of sensor 1

Figure 1. Fluorescence spectra of sensor 1 in aqueous solution [trace amounts of N,N-dimethylformamide (DMF)] with the addition of 20 equiv. of metal ions Inset: the solution fluorescence change of sensor 1 (1 μmol/L) in the absence and presence of 20 equiv. Al 3+ (λex: 450 nm)

Figure 2. Fluorescence intensity of sensor 1 (1 μmol/L) with selected cations (20 equiv.) in the absence or presence of Al 3+ in aqueous solution

Figure 3. Fluorescence titration spectra of sensor 1 upon addition of Al3+ in aqueous solution (trace amounts of DMF) [Al3+]: 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 3.0, 4.0 and 5.0 equiv. The Job plot showed that sensor 1 formed a 1∶1 complex with Al3+

Figure 4. Fluorescence spectra of complex 1-Al3+ in aqueous solution (trace amounts of DMF) with the addition of 10 equiv. of different anions

Figure 5. Fluorescence intensity of complex 1-Al3+ (1 μmol/L) with selected anions (10 equiv.) in the absence or presence of pyrophosphate (PPi) in aqueous solution

Figure 6. Fluorescence titration spectra of complex 1-Al3+ upon addition of PPi in aqueous solution (trace amounts of DMF) [PPi]: 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, 3.0, 4, 5, 6, 7, 8, 9 and 10 equiv. The Job plot indicated that 1-Al3+ formed a 1∶1 complex with Ppi

Figure 7. 1H NMR titration spectra of sensor 1 upon addition of 0.2 equiv. Al3+

Scheme 2. Possible mechanism of sensor 1 for Al3+ and 1-Al3+ for PPi

Figure 8. Change of fluorescence intensity recorded for sensor 1 toward Al3+ and PPi under various pH values in aqueous solution (trace amounts of DMF) medium at room temperature

Figure 9. Sequential recognition of sensor 1 (1 μmol/L) upon alternate addition of Al 3+ and PPi in aqueous solution (trace amounts of DMF) The inset shows the alternate change of the fluorescence color of the test solution after Al3+ and PPi are alternately added.

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一种基于香豆素骨架的荧光化学传感器于水溶液中实现对Al³⁺和焦磷酸根(PPi)的连续识别

A Fluorescent Chemosensor Based on Coumarin for Squential Recognition of Al³⁺ and Pyrophosphate (PPi) in Aqueous Solution

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