NL2030223A - MOLECULAR PROBE CAPABLE OF DYNAMICALLY DETECTING Fe3+ and AI3+ IN WATER AND USE THEREOF - Google Patents
MOLECULAR PROBE CAPABLE OF DYNAMICALLY DETECTING Fe3+ and AI3+ IN WATER AND USE THEREOF Download PDFInfo
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Abstract
The present disclosure relates to the technical field of performance detection of organic compounds, and discloses an aminofluorene Schiff base molecular probe. The 5 aminofluorene Schiff base molecular probe is prepared by a one-step polymerization reaction with 2,3-dihydroxybenzaldehyde and 2,7-diaminofiuorene as reaction raw materials. The molecular probe contains three metal ion action sites of imine and 0- dihydroxy and has a significant "off—on" fluorescence detection response to Al3+, an "off- on-off“ dual fluorescence detection signal to different concentrations of Fe“, sensitive quantitative detection performance for Fe3+ and a significant use value. In addition, a preparation method of the molecular probe has a high yield, a simple preparation process, easy implementation and other advantages and is suitable for industrial popularization, and favorable conditions are created for popularization and use of the aminofiuorene Schiff base molecular probe.
Description
MOLECULAR PROBE CAPABLE OF DYNAMICALLY DETECTING Fe’ and
AB" IN WATER AND USE THEREOF
[01] The present disclosure relates to the technical field of performance detection of organic compounds, and specifically relates to an aminofluorene Schiff base molecular probe having sensitive off-on-off and off-on fluorescence detection signals for Fe** and
Al** in water respectively and use thereof.
[02] With development of society, environmental pollution has become a hotspot of global concern and also one of main problems in sustainable development of economy and society in China. For example, metals such as iron and aluminum are widely used in current industrial production. However, when the metals are discharged into nature in the form of cations with industrial wastewater, an entire water system is seriously polluted, and great harm is caused to an ecosystem and a human living environment. In particular, the metal ions discharged into an ecological environment are difficult to degrade and easy to enrich and expand in biological chains. After water and food polluted by the metals are drunk or eaten by people, the metal ions are accumulated in the human body, resulting in serious harm to the human body. For example, the iron is one of essential trace elements in the human body, but when there are too much iron ions in the human body, abnormal liver functions, myocardial damage, diabetes, tumors, osteoporosis and the like may be caused; and when the aluminum is accumulated in the brain, brain neurodegeneration, memory decline and even Alzheimer disease may be caused. Therefore, development of a method for sensitive and rapid detection of the metal ions in the water has a great meaning in chemistry and chemical engineering, industrial and agricultural production, environmental science and other fields.
[03] In many methods for analyzing and detecting the metal ions, fluorescent molecular probes have become one of hotspots of researches due to high sensitivity, low cost, easy operation and other characteristics. The fluorescent molecular probes are used for converting recognition information in a microscopic world into easy-to-detect optical signals on the basis of molecular recognition, and usually dispersed in a detection system in an independent molecular state for emitting detection signals. Therefore, in-situ and real-time detection at a single-molecule level is realized, and analysis results are sensitive and accurate. According to different detection requirements, a large number of fluorescent molecular probes for detecting Fe’*, Al’ and the like have been prepared.
However, most of the fluorescent molecular probes at present have a sensitive detection function only for a specific metal ion, and the function is relatively monotonous. In addition, fluorescence intensity signals of most of the reported fluorescent molecular probes are only monotonously increased or reduced with changes of concentration of
Fe**, and there are few reports on sensitive molecular probes whose fluorescence signals have an "off-on-off" bidirectional change with the changes of the concentration of Fe**.
In actual work, there are more and more demands for detection of dynamic changes of the concentration of Fe**. Therefore, development of sensitive and easy-to-prepare fluorescent molecular probes for dynamic detection of Fe** is currently needed urgently in various monitoring fields.
[04] During construction of the fluorescent molecular probes, structural characteristics of easy coordination of the metal ions are combined. When ion receptors are designed, groups containing N, O, S and other atoms with a strong coordination ability are generally selected as metal ion binding sites and connected to fluorescent signal groups by a specific connection method. The microscopic recognition information of the metal ions is converted into easy-to-test spectral signals, and the fluorescent molecular probes with metal ion detection performance are obtained. Due to high photostability, easy structural modification and other characteristics, a rigid conjugated fluorene group is an excellent fluorescence signal group. An easy-to-synthesize imine
Schiff base (-C=N-) group has a strong metal coordination ability. After the -C=N- group is introduced into a fluorescent molecule, complexation and selectivity between the molecule and the metal ions can be improved. In addition, due to a p-z conjugation effect after the C=N- group is connected to the fluorescence group, conjugation of the fluorescent molecule can be improved. After a nitrogen atom in the -C=N- group is coordinated with a heavy metal ion, a conjugation degree of the fluorescent molecule can be changed, so that the fluorescent molecule has sensitive spectral signal changes.
After the two groups above are combined, a series of fluorescent molecular probes having different recognition properties are prepared [A. Hens, A. Maity, K. K. Rajak,
Inorg. Chim. Acta, 2014, 423, 408; J. Zhang, Z. Zhao , H. Shang, Q. Liu, F. Liu, New J.
Chem., 2019, 43, 14179; F. Wang, C. Li, X. Zhang, A. Wang, L. Zhou, C. Jia, J. Xu, Y.
Chen, Dves and Pigments, 2019, 171, 107667]. However, there are no reports on multifunctional fluorene Schiff base fluorescent molecular probes having sensitive "off- on-off" and "off-on" fluorescence detection signals for Fe'* and AI" respectively.
[05] A technical objective of the present disclosure is to provide a multifunctional fluorescent molecular probe having sensitive "off-on-off" and "off-on" fluorescence detection signals for Fe?” and AI** in water respectively.
[06] Another technical objective of the present disclosure is to provide a method for dynamically detecting Fe** and Al*" in water for people to work and live. The method has a fast and sensitive effect, easy operation, a low cost, easy popularization and other advantages.
[07] In order to achieve the objectives above, the present disclosure adopts the following technical solutions.
[08] An aminofluorene Schiff base fluorescent molecular probe capable of dynamically detecting Fe’ and Al°* in water has a molecular structure shown as follows:
HO OH
4
U CDR
HO OH
[09]
[10] A preparation method of the aminofluorene Schiff base fluorescent molecular probe capable of dynamically detecting Fe** and AI** in water includes the following steps:
[11] placing a mmol of 2,3-dihydroxybenzaldehyde into a round-bottom flask containing B mL of absolute ethanol, and raising the temperature for reflux; adding y mmol of 2,7-diaminofluorene for a continuous reaction for 3-5 hours; and then conducting filtration, washing with absolute ethanol and drying on a mixture obtained after the reaction to obtain the deep red aminofluorene Schiff base fluorescent molecular probe; where a:B:y is 2:20:1.
[12] A preparation reaction formula of the aminofluorene Schiff base fluorescent molecular probe capable of dynamically detecting Fe’* and AI?” in water is as follows:
HO OH a HO OH
[13]
[14] The present disclosure has the following technical effects: a receptor unit of the aminofluorene Schiff base fluorescent molecular probe contains three metal ion action sites of imine and o-dihydroxy. When concentration of Fe’ in a solution is constantly increased, the maximum fluorescence emission of the molecule at 410 nm is significantly increased first and then reduced, there is a sensitive “off-on-off" dual fluorescence detection signal, and the molecular probe has sensitive quantitative detection performance for Fe**. However, when concentration of AlI** in the solution is constantly increased, the maximum fluorescence emission intensity of the molecule at 410 nm is significantly improved, and the molecule has many detection functions and a high use value. A preparation process of the aminofluorene Schiff base fluorescent molecular probe provided in the present disclosure has a simple preparation process, mild reaction conditions, a high yield and other advantages, industrial implementation is suitable, and favorable conditions are created for popularization and use of the aminofluorene Schiff base fluorescent molecular probe.
[15] FIG. 1 is a hydrogen nuclear magnetic resonance (NMR) spectrum of compounds obtained in Examples 1 to 2.
[16] FIG. 2 is a fluorescence emission spectrum of an aminofluorene Schiff base fluorescent molecular probe in a 95% N,N-dimethylformamide (DMF) aqueous solution after different metal ions are added.
[17] FIG. 3 is a fluorescence emission spectrum of an aminofluorene Schiff base fluorescent molecular probe in a 95% DMF aqueous solution after different concentrations of Fe’* are added.
[18] FIG. 4 is a fluorescence emission spectrum of an aminofluorene Schiff base fluorescent molecular probe in a 95% DMF aqueous solution after different concentrations of A[** are added.
[19] FIG. 5 is a fluorescence emission spectrum of an aminofluorene Schiff base fluorescent molecular probe in a 95% DMF aqueous solution after 10 times of Al** and other different metal ions are added.
5 [20] The present disclosure discloses an aminofluorene Schiff base fluorescent molecular probe capable of dynamically detecting Fe’* and AI** in water, and a molecular structure of the molecular probe is shown as follows:
HO OH
SCH
—
HO OH
[21]
[22] The molecular probe can be prepared by a one-step polymerization reaction with 2,3-dihydroxybenzaldehyde and 2,7-diaminofluorene as reaction raw materials, and a preparation reaction formula is as follows:
HO OH a HO oH
SL Hd oH
[23]
[24] Example 1
[25] 2 mmol of 2,3-dihydroxybenzaldehyde was placed into a round-bottom flask containing 20 mL of absolute ethanol, and the temperature was raised for reflux; 1 mmol of 2,7-diaminofluorene was added for a continuous reaction for 3 hours; and then filtration, washing with absolute ethanol and drying were conducted on a mixture obtained after the reaction to obtain 235.4 mg of a deep red aminofluorene Schiff base fluorescent molecular probe A with a yield of 54%.
[26] Example 2
[27] 2 mmol of 2,3-dihydroxybenzaldehyde was placed into a round-bottom flask containing 20 mL of absolute ethanol, and the temperature was raised for reflux; 1 mmol of 2,7-diaminofluorene was added for a continuous reaction for 5 hours; and then filtration, washing with absolute ethanol and drying were conducted on a mixture obtained after the reaction to obtain 236 mg of a deep red aminofluorene Schiff base fluorescent molecular probe B with a yield of 54%.
[28] The compounds A and B obtained in Examples 1 to 2 were analyzed and determined, and hydrogen NMR spectra of the two compounds were consistent. Data were as follows: in tH NMR (DMSO-ds, 400 MHz), there were 4 OH proton signal peaks of 13.79 (s, 2H) and 9.75 (s, 2H), 2 proton signal peaks of 8.90 (s, 2H) on C=N-carbon, 12 aromatic ring proton signal peaks of 8.51 (s, 2H), 7.97 (d, 2H), 7.64 (s, 4H), 7.44 (d, 2H), 6.99 (d, 2H) and 6.46 (d, 2H) and 2 CH2-proton signal peaks of 4.02 (s, 2H) on a fluorene group. The data were basically consistent with theoretical values of an aminofluorene Schiff base fluorescent molecule. Therefore, it could be confirmed that the compounds A and B had a molecular structure shown as follows:
HO OH
Es 3
CAD
HO OH
[29] ‚ and the molecular structure showed the aminofluorene Schiff base fluorescent molecule.
[30] Example 3
Fluorescence detection performance of an aminofluorene Schiff base fluorescent molecule for different metal ions in a 95% DMF aqueous solution: In the 95% DMF aqueous solution, the aminofluorene Schiff base fluorescent molecule with a concentration of 2x10” mol/L had a weak fluorescence emission peak near 410 nm.
After a 10 times molar equivalent of Fe** was added, the maximum fluorescence emission intensity of the aminofluorene Schiff base fluorescent molecule at 410 nm was improved by 2.4 times and blue-shifted to a position near 405 nm. After a 10 times molar equivalent of AlI** was added, the maximum fluorescence emission of the probe molecule was blue-shifted to a position near 403 nm, and the fluorescence intensity was improved by 17.8 times. After other metal ions such as Lit, Na’, K*, Ba?*, Ca",
Mg**, Ag”, Co?*, Hg?*, Mn**, Ni?*, Cd?* and Zn?" were added, the maximum fluorescence emission of the compound was changed slightly at 410 nm. These data indicated that the aminofluorene Schiff base fluorescent molecule had different fluorescence detection responses to Fe** and AD".
[31] Example 4
[32] Fluorescence detection performance of an aminofluorene Schiff base fluorescent molecule for different concentrations of Fe** in a 95% DMF aqueous solution: In the 95%
DMF aqueous solution containing the aminofluorene Schiff base fluorescent molecule with a concentration of 2x10” mol/L, different concentrations of Fe’* were separately added, where molar equivalent ratios of the aminofluorene Schiff base fluorescent molecule to Fe** were 1:0, 1:0.2, 1:0.4, 1:0.6, 1:08, 1:1.0, 1:1.2, 1:1.4, 1:1.6, 1:1.8, 1:2.0, 1:2.5, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10 and 1:20 respectively. A detailed fluorescence emission spectrum data research showed that when a mass of Fe’ in the aqueous solution was constantly increased from 0 to 3 times, the maximum fluorescence emission of the aminofluorene Schiff base fluorescent molecule near 410 nm was significantly increased to 11 times and slightly blue-shifted to 405 nm. When the mass of Fe** was continuously increased from 3 times to 10 times, the fluorescence emission intensity was significantly reduced. When the mass of Fe’* was continuously increased to 20 times, a fluorescence emission spectrum was basically unchanged. It was indicated that the aminofluorene Schiff base fluorescent molecular probe had a dynamic "off-on-off" dual fluorescence signal detection potential for different concentrations of Fe" in the 95%
DMF aqueous solution.
[33] Example 5
[34] Fluorescence detection performance of an aminofluorene Schiff base fluorescent molecule for different concentrations of Al** in a 95% DMF aqueous solution: In the 95%
DMF aqueous solution containing the aminofluorene Schiff base fluorescent molecule with a concentration of 2x10” mol/L, different concentrations of AI’ were separately added, where molar equivalent ratios of the aminofluorene Schiff base fluorescent molecule to Al** were 1:0, 1:0.2, 1:0.4, 1:0.6, 1:0.8, 1:1.0, 1:12, 1:1.4, 1:1.6, 1:1.8, 1:2.0, 1:2.5, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10 and 1:20 respectively. A systematic fluorescence emission spectrum property research showed that when the concentration of AI’ in the solution was constantly increased from 0 to a 10 times molar equivalent, the maximum fluorescence emission intensity of the aminofluorene Schiff base fluorescent molecule near 410 nm was significantly improved and blue-shifted to 403 nm. It was indicated that the aminofluorene Schiff base fluorescent molecule had a sensitive "off-on" fluorescence signal detection potential for Al°* in the 95% DMF aqueous solution.
[35] Example 6
[36] Selective competitive performance of an aminofluorene Schiff base fluorescent molecule for Fe** and other metal ions in a 95% DMF aqueous solution: In the 95%
DMF aqueous solution containing the aminofluorene Schiff base fluorescent molecule with a concentration of 2x10” mol/L, 10 times molar equivalents of Fe** and other different metal ions were separately added. A fluorescence emission spectrum research of a mixed system showed that after a 10 times molar equivalent of Fe** was added, the aminofluorene Schiff base fluorescent molecule had a medium-intensity fluorescence emission near 405 nm. After metal ions such as Li*, Nat, K*, Ba?*, Ca?’ Mg?*, Ag’,
Co**, Hg?*, Mn?*, Ni¥*, Cd?*, Zn?" and Al** were added into a mixed system of the aminofluorene Schiff base fluorescent molecule and Fet a fluorescence emission spectrum was basically unchanged. It was indicated that when there were Fe’* and other metal ions, the aminofluorene Schiff base fluorescent molecule stilled had great selective detection performance for Fe**.
[37] Example 7
[38] Ultraviolet and fluorescence performance of different metal ions in a 95% DMF aqueous solution: In a mixed solvent of DMF and water at a volume ratio of 95:5, after metal ions such as Li*, Nat, K*, Ba?*, Ca¥’, Mg?*, Agt, Co’, Hg?*, Mn? Ni?*, Cd,
Zn’*, AI’ and Fe’* were separately added, a fluorescence emission spectrum was unchanged.
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| CN202111145898.8A CN113861067B (en) | 2021-04-26 | 2021-09-28 | But dynamic detection aquatic Fe 3+ Al and Al 3+ Molecular probe and application thereof |
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| CN107699234B (en) * | 2017-10-23 | 2019-06-21 | 东南大学 | A kind of Schiff bases Multifunction fluorescent probe and its preparation method and application |
| CN110407717B (en) * | 2018-04-27 | 2022-09-13 | 北京市环境保护科学研究院 | P-diethylamino salicylaldehyde modified fluorene fluorescent probe and preparation method thereof |
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